Patent
US 10,014,475GRAPHENE NANORIBBONS AS SEMICONDUCTORS FOR ORGANIC THIN FILM TRANSISTORS
Josef Peter KLEIN
US
Copyright © 2026 Matter42. All rights reserved.
Patent
Atlas literature
Patent
US 10,014,475Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(Currently Amended) A method fo r synt h esizing a g raph ene nanor ibbon, the method c onprising: cou pling a first aryl m ono m er and a second a r y l monomer to provide a linea rly COnTUU gated 4ry compound intennedh ate; end capping the line arl y c onjugated arytl compound intermediate; coupling the lineary cnjugateo try compound intermediate with a mono-subst ituted acetyl eneco.mpo und to p ro vide a line arly conju gat e d ar yl compound h av ing a for mula (B); SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.1.svg 3.03 3.21 Black and white (1) w herei n n is an integer of I to I 00, t)00; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.2.svg 0.22 4.63 Black and white Rs to R, a re i ndep end en tly selected from H, alkyl, aryl, and tri m ethylsily l;[and]] P erf ort ing p olycycl i zatio n of the linearly conj ugated aryl co mpou nd t o provide a gra phene nanco ribbon precursor, wherein perf ormin g polycyclizati o n of the linearly conjugated aryl compound to provide a grap hene nanori bbo n precursor c om prises heatin g to a te m pera ture of about 20 ' C to about 150 * C for ab out I to about 36 hours; and perf i-w ming cyclode hydrogena tion of th e grap hene na noribbon precursor to provide the grap hene nanoribbon, Currently amended
T he method of claim 1, wherein perronin g the cyclodeh y dr o g ena. tion of the gr aphe ne n anoribbon pre cur sor to provide the graphene n anoribbo n comprises performi ng oxidative c ycl ode hyd roge nat ion of the gra phene nan oribbon prec urs or. Previously presented
(Previously Presente d) The method o f claim 1, wh ere in per fornin g the cyc lod ehy drogeu ation of the graphene nanor ibbon precu rs or to provide the graphene na n ori b bon comprises c ontacti ng the gra ph ene nanoribbon precursor with iron (Iii) chloride. Previously presented
(C u rren tl y Amended) A method, f o r synthesizing a ara phen e nan oribb onn the method comprisig, coupling a first aryl monomer and a second ar yl mono m er to provide a linearly on.jugated aryl co mpotmd interm ediat e; coupling the l inearly co n jugat ed aryl compound inte rme diate with a mono- su bst ituted acetylene compound to provid e a linearly conjugated aryl compound h avi n g a fo rmu la (I): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.3.svg 3.03 3.21 Black and white wherein a is an ntcge r of I to 1 09,00 9; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.4.svg 0.23 4.65 Black and white R to 1 ar e indep ende ntly selected f rom 1I, alkyl, aryl and trimethylsilyl; erforming polcyclizauion of the li early convgaled aryl pomnpQoud to provide a graphene nanorib bon precursor; and p erfor ming cycl dehydrogenation of the gr aphen e n anor ibbon precurs o r to pro yide the raphene noribbon. Currently amended
(Pre v iously Pr esented) The method of claim 2, wherein the first ar yl monomer ha s a formul a (V) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.7.svg 1.59 1.86 Black and white (V) wherein R 1 to R. are indep enden tly selected from h ydrog e n, fluorine, chlorine, bromine, iodi n e, lithium, trifiuorometbanesulfonate, mesy late, t osylat e, bismuth, a b oronic acid, a bo r onic ester, a boronate ester, an organobora ne, an o rgan otrifl uorobo rate, a magnesiu m halide, a stannane, a s ili con triha hide, an org anos ilan e, an. acet y lox y, a n d a zinc halide; and wherein the second a ryl mono mer has a fo rnula (VI) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.8.svg 1.59 1.99 Black and white (VI) wherein R 7 to R are indep e nde n tly selected from hydrogen, f luorine, chlorine, bro mine, iodine, lithiu m, tifl [oromethanesulftonate, me sylate, tosyl at e, bis m uth, a b oro nic acid, a b oronic ester, a boronate ester, an or gantobora ne, an or gano mtfluoro borat e, a ma gne sium halide, a stannan e, a si lic on t rihal ide, an orga nosil ane. an acetylo xy, and a zin c halide. Previously presented
The method o f claim 2, wherein coupling a first aryl monom er and a second aryl mono m er to provide a linearly c,.jugated iryl compound imterm ediate further comprises heating to a temperature of about 20 C to about 120 C fo r a period of about 1 hour to about 36 hImus. Previously presented
23. (Original) T he m ethod of claim 2 2, furth er c ompr isi ng adding a solvent. Original
The method of clai m 2, whe rein the f irst aryl m onomer is a dihal ophen yl dibo r onate compound and the second ar yl mono mer is a di ha lodiodobenzene compound. Original
IThe meth o d of c llain 2., whe rein c oup lin g a fir s t ar yl monomer and a seco nd aryl monomer to provide a linearly co nju gated aryl co mpound intermediate comprises con tacti ng the first ar yl m onomer with the s ec ond aryl monome r i n a mol ar ratto o f abo ut 2:1 to about 1:2. Original
10, The method of claim 9, wh erein coupling a first ar yl monomer a n d a second aryl m ono mer to provide a linearly c onju gated aryl compound intermediate furth er comprises ad din g a catalyst, Original
- 18. Canceled
Canceled
2 0. The method of clai m 2, further com prising c oup ling the line ar ly conjug ate d aryl c omp ound inte rme diate with a mono-substituted acetylene c o mpo un d to form the linearly c o njugated aryl compound, whe rein the mono-substituted acetyle n e compound has a f ormula (IV): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.9.svg 0.16 1.45 Black and white (IV) wh erei n R n is s e lected f ro m h ydrogen, aryl, polycyclic aryl., alkyl, c opper, zin c, magresium, tin, boron, si lic on, imdium, a luminum, lit hium, sodium, zin c chloride, mercury chloride, mang anese (11) chloride, magnesium bromide, triutyl boron lithium, tributyl aluminum lithi um, dib u tyl a lumin um., trim ethy l silicon, tributy l tin, or b is(cyc l ope n tadien yl)d imethy l zirconium; and R 1 3 is sel ec ted from hydrog en, t rimethy lsilyl, te rt-buty ldi m ethylsilyl, t ert- but y ldip henylsilyl, triethy lsilyl, tri isoprop yls ily l, alkyl, phenyl, f ura nyl, th i opheny l. pyridyl, or poly (m -phenylene) comprising abo u t 2. to about 20 m-pheny lene u n its. Previously presented
21. (Orig in al) The m ethod of claim 20, wherein R i is hydrogen and R is trimethylsilyl. Original
22. (Origin al) The method of cla im 20, wherein co up ling the li ne arly co n jugated aryl compound inter m ediat e with a mono-suhstituted acetylene co mpou nd to f orm the l inea rly conju gated aryl compound fu rther comprises contacting the linearly conjugated aryl compo und with a fluoride source. Original
- 26 Canceled
Canceled
2 7. The meth od of claim [[-?6]1, wherein en dc apping the linearly conjugated aryl co m pou n d inte rm ediate occurs prior to the poly ccl ization of the linearly co nju g ated aryl compound to provide a g raphene nan o ribbon precur sor. Currently amended
28 (Currently A m ended) The method of clai m [[26]], wherein e ndeap ping the linearly co nj ugated aryl compound intermediate comprises coupling t h e li n early co 'jugat ed aryl compo und inte rm ediate wi th an aryl m ono m er of form u la (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.10.svg 1.15 1.42 Black and white (VI I) wherein R:4 is hydrogen, fluorine, chlorine, bromine, iodine, lithium, trifluoromeihanesulfnate, m esylate, or t o sylate; and wherein RTh is hydrogen, flu otine, chlorine, bromine, iodine, lithium, tridluoromethanesulf) nate, m esy late, tosylate, bismu th, a bor o nic acid, a bo r onic ester, a boronate ester, an orga n obo rane, an organ o tri fluoroborate, a mag nesium halide, a st anane., a silicon tri h alide, an or g anosilane, an acetylo xy, or a zin c halide. Currently amended
T he m ethod of claim 28, wherein the uns ub stituted rin g carbons on the aryl monomer of fbrmnula VI. are i ndependently sub stit uted with groups selected from hydrogen, hydroxyl, a substit u ted or uns u bstituted (C j-C₂₀)al kyl, (C-20) hydroxyalkyl, (C'~ C₂) alk ox y, (C p-C₂)alklicarboxy, a substituted or unsubstituted aryl., (C 1-Ca)h aloalk vl, (C-~ Ce) alk e nyl, (C₂C)al kynyl, o r an oxo. Previously presented
(C u rrently A m ended) T he method of claim [[26]1 1. wherein e ndeap pin g the linearly co nju gated aryl compound inter m ediate comprises cou pli n g the linearly conjuga t ed ary l compound in termed i ate wi th a 2 -br omoph enyl b oronate, a 2-hl orophenyl boro na te, 2-b romo 1 io dobenzen c, 2-chl o ro- I-io doben zene, o r a combination thereof. Currently amended
The m e thod of clai m [[26 111, wherein end e apping the linearly co rnjugat ed aryl compound intermediate c om prises add i ng a pal ladium ca talys t, a copper salt, an aqueous base, or a c o mbinat io n there of. Currently amended
3 6. (Cu rre ntly Ame n ded) The m ethod of claim [[26]] 1. wherein endcappin g the linearly conjugated aryl c o mpo und intermediate comprises heatin g to a temperature of about 20 C to about 15(0 C for abou t I to about 3 6 hours. Currently amended
Canceled
(Canceled) Canceled
(Origin al) the me thod of cl aim 37, f urther comprising adding a solvent. Original
- 4 3. Canceled
Canceled
- 52. 9 Canceled
Canceled
(Withdrawn-Previously P resented) A method of synt he sizing a gr aphene nanorib bon havi ng a zigzag bac kbone; the metid compnri sin g providing a zigzag con jugat ed aryl comp ound having a formula (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.11.svg 1.39 5.23 Black and white (VI) wherein R 1.and R 3 are indep en dently selected fr om lhydro gen, fluorine, chlorine, b rom ine, iodine, lithium, trifluoromethanesulfbnat, mesyla te, tos ylate, bismuth, a bor onic acid, a boronic ester, a boron ate ester, an o rgan oborane, a n or g anot rifluoroborate, a. ma g ne sium halide, a sta nnane, a silicon t riafide, a org anosilan e, an ac ut yloxy, and a zine halide; wh erein R 2 is hydronge, tr imet hyl silyl, rt-butyl dimeth ylsilyi, te rIbutyldiphenylsilyl, triet hylsilyl, trii sopropylsi lyl, alkyl., phenyl, furanyl, t hiophenyl, pyridyl, or po ly (n-ph enylene) compri s ing about 2 to about 20 tn-ph enyl ene units, wherein R 4 to R.- are independently selected from an alde hyd e group and an acetal group; and po lycyclizing the zigzag conj u gated aryl compou nd t o provi de a graphene na nor ibbon p recurso r. Withdrawn
(Withdrawn-Previo u sly Presented) The me thod o f claim 53, wherein the fi rst aryl monome r has a formula (VII): Respo n se to Non-i-Final Office Action mailed o n September 26, 2 017 SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.12.svg 1.81 1.64 Black and white (VII) w her ein R is hydrogen, t rimethylsilyl, tert-utayldinethylsilyl. tertbtyldiphenyilsilyl, tri ethlyl silyl, triisopropy l sily l, al kyl, phenyl, furanyl, thioph enyl., py ri dy, or po ly (m.-phcny len c) com pris in g about 2 to about 20 m -ph enylene ui ts; wherein R 2 to R; are independently selected from b ydro gen, f l uori n e, chlorine, bromine, i odine, lith i um, trnfluoromethanesutonate, m esylate., tosy l ate, bismu th, a bor o nic a cid, a boro nic ester, a boronate ester, an organ oborane, an org an otri fluorobor ate, a magnesium halide, a stannane, a silicon. tri h alid e, an o rganosilane, an acetyloxy, and a zinc hal i de, w herein at least tw o of R 2 t o R d are not hydro g en; and wherein the second aryl mon omer has a lonm ula. (V III): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.13.svg 0.89 2.23 Black and white (VIII) wherein R 7 and R s are independently selected from hydrogen, fluorine, chlorine, bromine, iodin e, lithium, t rifluorome thanes ulfonate, m esylate, tosylate, bis m uth, a b oron ic acid, a boronic este r, a horonat e ester, an org anobo rane, an or ganotrifl uorobo rate, a magn esium halide, a st a nnan e, a sili con tri hali de, an orgta nosilane, an acet yloxy, and a zi nc halide: and wherein R Q and R m are independently selected from an aldehyde g r oup and an acetal group. Withdrawn
56, (Withdra w n-Previously P res ented The method o f claim 53, frirth er c omp ris ing c oupling a first a ryl monom er and a second aryl mo nomer to pr ovide a zigzag conju gated aryl compoun d i ntermed iate wherein the first aryl mono me r is 2-t rni ethy l sil yl-1,3-d ibo ron ic acid an d the second aryl mono me r is 4,6-bis(bromomethyhisophthaladehyde.
57, (Withdrawn-Previously P resented) The m ethod o f claim 53, wh e rei n c ouplin g a first aryl monomer and a se c ond ary l monomer to provide a zigzag co nju gated aryl compound intermediate comprises contacting the first aryl monomer with the seco n d a ryl monomer in a mola r ra ti o of ab ou t 2:1 to about 1:2. Withdrawn
(Withdrawn-Previously Presented) The m ethod of claim 53, w here in coupling a first aryl monom er and a second aryl monom er to provide a zigza g conjugated aryl compoun d fu rther comprises adding a cataly st. Withdrawn
(Can celed) Canceled
2 59,62. Canceled
Layer stacks claimed or described, ordered top of device to substrate.
organic thin film transistor
Materials described outside the worked examples.
graphene nanoribbon
linearly conjugated aryl compound
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Temperature | 20–120 °C | — |
Duration |
Patent
Atlas literature
Patent
US 10,014,475Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(Currently Amended) A method fo r synt h esizing a g raph ene nanor ibbon, the method c onprising: cou pling a first aryl m ono m er and a second a r y l monomer to provide a linea rly COnTUU gated 4ry compound intennedh ate; end capping the line arl y c onjugated arytl compound intermediate; coupling the lineary cnjugateo try compound intermediate with a mono-subst ituted acetyl eneco.mpo und to p ro vide a line arly conju gat e d ar yl compound h av ing a for mula (B); SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.1.svg 3.03 3.21 Black and white (1) w herei n n is an integer of I to I 00, t)00; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.2.svg 0.22 4.63 Black and white Rs to R, a re i ndep end en tly selected from H, alkyl, aryl, and tri m ethylsily l;[and]] P erf ort ing p olycycl i zatio n of the linearly conj ugated aryl co mpou nd t o provide a gra phene nanco ribbon precursor, wherein perf ormin g polycyclizati o n of the linearly conjugated aryl compound to provide a grap hene nanori bbo n precursor c om prises heatin g to a te m pera ture of about 20 ' C to about 150 * C for ab out I to about 36 hours; and perf i-w ming cyclode hydrogena tion of th e grap hene na noribbon precursor to provide the grap hene nanoribbon, Currently amended
T he method of claim 1, wherein perronin g the cyclodeh y dr o g ena. tion of the gr aphe ne n anoribbon pre cur sor to provide the graphene n anoribbo n comprises performi ng oxidative c ycl ode hyd roge nat ion of the gra phene nan oribbon prec urs or. Previously presented
(Previously Presente d) The method o f claim 1, wh ere in per fornin g the cyc lod ehy drogeu ation of the graphene nanor ibbon precu rs or to provide the graphene na n ori b bon comprises c ontacti ng the gra ph ene nanoribbon precursor with iron (Iii) chloride. Previously presented
(C u rren tl y Amended) A method, f o r synthesizing a ara phen e nan oribb onn the method comprisig, coupling a first aryl monomer and a second ar yl mono m er to provide a linearly on.jugated aryl co mpotmd interm ediat e; coupling the l inearly co n jugat ed aryl compound inte rme diate with a mono- su bst ituted acetylene compound to provid e a linearly conjugated aryl compound h avi n g a fo rmu la (I): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.3.svg 3.03 3.21 Black and white wherein a is an ntcge r of I to 1 09,00 9; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.4.svg 0.23 4.65 Black and white R to 1 ar e indep ende ntly selected f rom 1I, alkyl, aryl and trimethylsilyl; erforming polcyclizauion of the li early convgaled aryl pomnpQoud to provide a graphene nanorib bon precursor; and p erfor ming cycl dehydrogenation of the gr aphen e n anor ibbon precurs o r to pro yide the raphene noribbon. Currently amended
(Pre v iously Pr esented) The method of claim 2, wherein the first ar yl monomer ha s a formul a (V) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.7.svg 1.59 1.86 Black and white (V) wherein R 1 to R. are indep enden tly selected from h ydrog e n, fluorine, chlorine, bromine, iodi n e, lithium, trifiuorometbanesulfonate, mesy late, t osylat e, bismuth, a b oronic acid, a bo r onic ester, a boronate ester, an organobora ne, an o rgan otrifl uorobo rate, a magnesiu m halide, a stannane, a s ili con triha hide, an org anos ilan e, an. acet y lox y, a n d a zinc halide; and wherein the second a ryl mono mer has a fo rnula (VI) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.8.svg 1.59 1.99 Black and white (VI) wherein R 7 to R are indep e nde n tly selected from hydrogen, f luorine, chlorine, bro mine, iodine, lithiu m, tifl [oromethanesulftonate, me sylate, tosyl at e, bis m uth, a b oro nic acid, a b oronic ester, a boronate ester, an or gantobora ne, an or gano mtfluoro borat e, a ma gne sium halide, a stannan e, a si lic on t rihal ide, an orga nosil ane. an acetylo xy, and a zin c halide. Previously presented
The method o f claim 2, wherein coupling a first aryl monom er and a second aryl mono m er to provide a linearly c,.jugated iryl compound imterm ediate further comprises heating to a temperature of about 20 C to about 120 C fo r a period of about 1 hour to about 36 hImus. Previously presented
23. (Original) T he m ethod of claim 2 2, furth er c ompr isi ng adding a solvent. Original
The method of clai m 2, whe rein the f irst aryl m onomer is a dihal ophen yl dibo r onate compound and the second ar yl mono mer is a di ha lodiodobenzene compound. Original
IThe meth o d of c llain 2., whe rein c oup lin g a fir s t ar yl monomer and a seco nd aryl monomer to provide a linearly co nju gated aryl co mpound intermediate comprises con tacti ng the first ar yl m onomer with the s ec ond aryl monome r i n a mol ar ratto o f abo ut 2:1 to about 1:2. Original
10, The method of claim 9, wh erein coupling a first ar yl monomer a n d a second aryl m ono mer to provide a linearly c onju gated aryl compound intermediate furth er comprises ad din g a catalyst, Original
- 18. Canceled
Canceled
2 0. The method of clai m 2, further com prising c oup ling the line ar ly conjug ate d aryl c omp ound inte rme diate with a mono-substituted acetylene c o mpo un d to form the linearly c o njugated aryl compound, whe rein the mono-substituted acetyle n e compound has a f ormula (IV): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.9.svg 0.16 1.45 Black and white (IV) wh erei n R n is s e lected f ro m h ydrogen, aryl, polycyclic aryl., alkyl, c opper, zin c, magresium, tin, boron, si lic on, imdium, a luminum, lit hium, sodium, zin c chloride, mercury chloride, mang anese (11) chloride, magnesium bromide, triutyl boron lithium, tributyl aluminum lithi um, dib u tyl a lumin um., trim ethy l silicon, tributy l tin, or b is(cyc l ope n tadien yl)d imethy l zirconium; and R 1 3 is sel ec ted from hydrog en, t rimethy lsilyl, te rt-buty ldi m ethylsilyl, t ert- but y ldip henylsilyl, triethy lsilyl, tri isoprop yls ily l, alkyl, phenyl, f ura nyl, th i opheny l. pyridyl, or poly (m -phenylene) comprising abo u t 2. to about 20 m-pheny lene u n its. Previously presented
21. (Orig in al) The m ethod of claim 20, wherein R i is hydrogen and R is trimethylsilyl. Original
22. (Origin al) The method of cla im 20, wherein co up ling the li ne arly co n jugated aryl compound inter m ediat e with a mono-suhstituted acetylene co mpou nd to f orm the l inea rly conju gated aryl compound fu rther comprises contacting the linearly conjugated aryl compo und with a fluoride source. Original
- 26 Canceled
Canceled
2 7. The meth od of claim [[-?6]1, wherein en dc apping the linearly conjugated aryl co m pou n d inte rm ediate occurs prior to the poly ccl ization of the linearly co nju g ated aryl compound to provide a g raphene nan o ribbon precur sor. Currently amended
28 (Currently A m ended) The method of clai m [[26]], wherein e ndeap ping the linearly co nj ugated aryl compound intermediate comprises coupling t h e li n early co 'jugat ed aryl compo und inte rm ediate wi th an aryl m ono m er of form u la (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.10.svg 1.15 1.42 Black and white (VI I) wherein R:4 is hydrogen, fluorine, chlorine, bromine, iodine, lithium, trifluoromeihanesulfnate, m esylate, or t o sylate; and wherein RTh is hydrogen, flu otine, chlorine, bromine, iodine, lithium, tridluoromethanesulf) nate, m esy late, tosylate, bismu th, a bor o nic acid, a bo r onic ester, a boronate ester, an orga n obo rane, an organ o tri fluoroborate, a mag nesium halide, a st anane., a silicon tri h alide, an or g anosilane, an acetylo xy, or a zin c halide. Currently amended
T he m ethod of claim 28, wherein the uns ub stituted rin g carbons on the aryl monomer of fbrmnula VI. are i ndependently sub stit uted with groups selected from hydrogen, hydroxyl, a substit u ted or uns u bstituted (C j-C₂₀)al kyl, (C-20) hydroxyalkyl, (C'~ C₂) alk ox y, (C p-C₂)alklicarboxy, a substituted or unsubstituted aryl., (C 1-Ca)h aloalk vl, (C-~ Ce) alk e nyl, (C₂C)al kynyl, o r an oxo. Previously presented
(C u rrently A m ended) T he method of claim [[26]1 1. wherein e ndeap pin g the linearly co nju gated aryl compound inter m ediate comprises cou pli n g the linearly conjuga t ed ary l compound in termed i ate wi th a 2 -br omoph enyl b oronate, a 2-hl orophenyl boro na te, 2-b romo 1 io dobenzen c, 2-chl o ro- I-io doben zene, o r a combination thereof. Currently amended
The m e thod of clai m [[26 111, wherein end e apping the linearly co rnjugat ed aryl compound intermediate c om prises add i ng a pal ladium ca talys t, a copper salt, an aqueous base, or a c o mbinat io n there of. Currently amended
3 6. (Cu rre ntly Ame n ded) The m ethod of claim [[26]] 1. wherein endcappin g the linearly conjugated aryl c o mpo und intermediate comprises heatin g to a temperature of about 20 C to about 15(0 C for abou t I to about 3 6 hours. Currently amended
Canceled
(Canceled) Canceled
(Origin al) the me thod of cl aim 37, f urther comprising adding a solvent. Original
- 4 3. Canceled
Canceled
- 52. 9 Canceled
Canceled
(Withdrawn-Previously P resented) A method of synt he sizing a gr aphene nanorib bon havi ng a zigzag bac kbone; the metid compnri sin g providing a zigzag con jugat ed aryl comp ound having a formula (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.11.svg 1.39 5.23 Black and white (VI) wherein R 1.and R 3 are indep en dently selected fr om lhydro gen, fluorine, chlorine, b rom ine, iodine, lithium, trifluoromethanesulfbnat, mesyla te, tos ylate, bismuth, a bor onic acid, a boronic ester, a boron ate ester, an o rgan oborane, a n or g anot rifluoroborate, a. ma g ne sium halide, a sta nnane, a silicon t riafide, a org anosilan e, an ac ut yloxy, and a zine halide; wh erein R 2 is hydronge, tr imet hyl silyl, rt-butyl dimeth ylsilyi, te rIbutyldiphenylsilyl, triet hylsilyl, trii sopropylsi lyl, alkyl., phenyl, furanyl, t hiophenyl, pyridyl, or po ly (n-ph enylene) compri s ing about 2 to about 20 tn-ph enyl ene units, wherein R 4 to R.- are independently selected from an alde hyd e group and an acetal group; and po lycyclizing the zigzag conj u gated aryl compou nd t o provi de a graphene na nor ibbon p recurso r. Withdrawn
(Withdrawn-Previo u sly Presented) The me thod o f claim 53, wherein the fi rst aryl monome r has a formula (VII): Respo n se to Non-i-Final Office Action mailed o n September 26, 2 017 SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.12.svg 1.81 1.64 Black and white (VII) w her ein R is hydrogen, t rimethylsilyl, tert-utayldinethylsilyl. tertbtyldiphenyilsilyl, tri ethlyl silyl, triisopropy l sily l, al kyl, phenyl, furanyl, thioph enyl., py ri dy, or po ly (m.-phcny len c) com pris in g about 2 to about 20 m -ph enylene ui ts; wherein R 2 to R; are independently selected from b ydro gen, f l uori n e, chlorine, bromine, i odine, lith i um, trnfluoromethanesutonate, m esylate., tosy l ate, bismu th, a bor o nic a cid, a boro nic ester, a boronate ester, an organ oborane, an org an otri fluorobor ate, a magnesium halide, a stannane, a silicon. tri h alid e, an o rganosilane, an acetyloxy, and a zinc hal i de, w herein at least tw o of R 2 t o R d are not hydro g en; and wherein the second aryl mon omer has a lonm ula. (V III): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.13.svg 0.89 2.23 Black and white (VIII) wherein R 7 and R s are independently selected from hydrogen, fluorine, chlorine, bromine, iodin e, lithium, t rifluorome thanes ulfonate, m esylate, tosylate, bis m uth, a b oron ic acid, a boronic este r, a horonat e ester, an org anobo rane, an or ganotrifl uorobo rate, a magn esium halide, a st a nnan e, a sili con tri hali de, an orgta nosilane, an acet yloxy, and a zi nc halide: and wherein R Q and R m are independently selected from an aldehyde g r oup and an acetal group. Withdrawn
56, (Withdra w n-Previously P res ented The method o f claim 53, frirth er c omp ris ing c oupling a first a ryl monom er and a second aryl mo nomer to pr ovide a zigzag conju gated aryl compoun d i ntermed iate wherein the first aryl mono me r is 2-t rni ethy l sil yl-1,3-d ibo ron ic acid an d the second aryl mono me r is 4,6-bis(bromomethyhisophthaladehyde.
57, (Withdrawn-Previously P resented) The m ethod o f claim 53, wh e rei n c ouplin g a first aryl monomer and a se c ond ary l monomer to provide a zigzag co nju gated aryl compound intermediate comprises contacting the first aryl monomer with the seco n d a ryl monomer in a mola r ra ti o of ab ou t 2:1 to about 1:2. Withdrawn
(Withdrawn-Previously Presented) The m ethod of claim 53, w here in coupling a first aryl monom er and a second aryl monom er to provide a zigza g conjugated aryl compoun d fu rther comprises adding a cataly st. Withdrawn
(Can celed) Canceled
2 59,62. Canceled
Layer stacks claimed or described, ordered top of device to substrate.
organic thin film transistor
Materials described outside the worked examples.
graphene nanoribbon
linearly conjugated aryl compound
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Temperature | 20–120 °C | — |
Duration |
Patent
Atlas literature
Patent
US 10,014,475Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(Currently Amended) A method fo r synt h esizing a g raph ene nanor ibbon, the method c onprising: cou pling a first aryl m ono m er and a second a r y l monomer to provide a linea rly COnTUU gated 4ry compound intennedh ate; end capping the line arl y c onjugated arytl compound intermediate; coupling the lineary cnjugateo try compound intermediate with a mono-subst ituted acetyl eneco.mpo und to p ro vide a line arly conju gat e d ar yl compound h av ing a for mula (B); SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.1.svg 3.03 3.21 Black and white (1) w herei n n is an integer of I to I 00, t)00; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.2.svg 0.22 4.63 Black and white Rs to R, a re i ndep end en tly selected from H, alkyl, aryl, and tri m ethylsily l;[and]] P erf ort ing p olycycl i zatio n of the linearly conj ugated aryl co mpou nd t o provide a gra phene nanco ribbon precursor, wherein perf ormin g polycyclizati o n of the linearly conjugated aryl compound to provide a grap hene nanori bbo n precursor c om prises heatin g to a te m pera ture of about 20 ' C to about 150 * C for ab out I to about 36 hours; and perf i-w ming cyclode hydrogena tion of th e grap hene na noribbon precursor to provide the grap hene nanoribbon, Currently amended
T he method of claim 1, wherein perronin g the cyclodeh y dr o g ena. tion of the gr aphe ne n anoribbon pre cur sor to provide the graphene n anoribbo n comprises performi ng oxidative c ycl ode hyd roge nat ion of the gra phene nan oribbon prec urs or. Previously presented
(Previously Presente d) The method o f claim 1, wh ere in per fornin g the cyc lod ehy drogeu ation of the graphene nanor ibbon precu rs or to provide the graphene na n ori b bon comprises c ontacti ng the gra ph ene nanoribbon precursor with iron (Iii) chloride. Previously presented
(C u rren tl y Amended) A method, f o r synthesizing a ara phen e nan oribb onn the method comprisig, coupling a first aryl monomer and a second ar yl mono m er to provide a linearly on.jugated aryl co mpotmd interm ediat e; coupling the l inearly co n jugat ed aryl compound inte rme diate with a mono- su bst ituted acetylene compound to provid e a linearly conjugated aryl compound h avi n g a fo rmu la (I): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.3.svg 3.03 3.21 Black and white wherein a is an ntcge r of I to 1 09,00 9; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.4.svg 0.23 4.65 Black and white R to 1 ar e indep ende ntly selected f rom 1I, alkyl, aryl and trimethylsilyl; erforming polcyclizauion of the li early convgaled aryl pomnpQoud to provide a graphene nanorib bon precursor; and p erfor ming cycl dehydrogenation of the gr aphen e n anor ibbon precurs o r to pro yide the raphene noribbon. Currently amended
(Pre v iously Pr esented) The method of claim 2, wherein the first ar yl monomer ha s a formul a (V) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.7.svg 1.59 1.86 Black and white (V) wherein R 1 to R. are indep enden tly selected from h ydrog e n, fluorine, chlorine, bromine, iodi n e, lithium, trifiuorometbanesulfonate, mesy late, t osylat e, bismuth, a b oronic acid, a bo r onic ester, a boronate ester, an organobora ne, an o rgan otrifl uorobo rate, a magnesiu m halide, a stannane, a s ili con triha hide, an org anos ilan e, an. acet y lox y, a n d a zinc halide; and wherein the second a ryl mono mer has a fo rnula (VI) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.8.svg 1.59 1.99 Black and white (VI) wherein R 7 to R are indep e nde n tly selected from hydrogen, f luorine, chlorine, bro mine, iodine, lithiu m, tifl [oromethanesulftonate, me sylate, tosyl at e, bis m uth, a b oro nic acid, a b oronic ester, a boronate ester, an or gantobora ne, an or gano mtfluoro borat e, a ma gne sium halide, a stannan e, a si lic on t rihal ide, an orga nosil ane. an acetylo xy, and a zin c halide. Previously presented
The method o f claim 2, wherein coupling a first aryl monom er and a second aryl mono m er to provide a linearly c,.jugated iryl compound imterm ediate further comprises heating to a temperature of about 20 C to about 120 C fo r a period of about 1 hour to about 36 hImus. Previously presented
23. (Original) T he m ethod of claim 2 2, furth er c ompr isi ng adding a solvent. Original
The method of clai m 2, whe rein the f irst aryl m onomer is a dihal ophen yl dibo r onate compound and the second ar yl mono mer is a di ha lodiodobenzene compound. Original
IThe meth o d of c llain 2., whe rein c oup lin g a fir s t ar yl monomer and a seco nd aryl monomer to provide a linearly co nju gated aryl co mpound intermediate comprises con tacti ng the first ar yl m onomer with the s ec ond aryl monome r i n a mol ar ratto o f abo ut 2:1 to about 1:2. Original
10, The method of claim 9, wh erein coupling a first ar yl monomer a n d a second aryl m ono mer to provide a linearly c onju gated aryl compound intermediate furth er comprises ad din g a catalyst, Original
- 18. Canceled
Canceled
2 0. The method of clai m 2, further com prising c oup ling the line ar ly conjug ate d aryl c omp ound inte rme diate with a mono-substituted acetylene c o mpo un d to form the linearly c o njugated aryl compound, whe rein the mono-substituted acetyle n e compound has a f ormula (IV): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.9.svg 0.16 1.45 Black and white (IV) wh erei n R n is s e lected f ro m h ydrogen, aryl, polycyclic aryl., alkyl, c opper, zin c, magresium, tin, boron, si lic on, imdium, a luminum, lit hium, sodium, zin c chloride, mercury chloride, mang anese (11) chloride, magnesium bromide, triutyl boron lithium, tributyl aluminum lithi um, dib u tyl a lumin um., trim ethy l silicon, tributy l tin, or b is(cyc l ope n tadien yl)d imethy l zirconium; and R 1 3 is sel ec ted from hydrog en, t rimethy lsilyl, te rt-buty ldi m ethylsilyl, t ert- but y ldip henylsilyl, triethy lsilyl, tri isoprop yls ily l, alkyl, phenyl, f ura nyl, th i opheny l. pyridyl, or poly (m -phenylene) comprising abo u t 2. to about 20 m-pheny lene u n its. Previously presented
21. (Orig in al) The m ethod of claim 20, wherein R i is hydrogen and R is trimethylsilyl. Original
22. (Origin al) The method of cla im 20, wherein co up ling the li ne arly co n jugated aryl compound inter m ediat e with a mono-suhstituted acetylene co mpou nd to f orm the l inea rly conju gated aryl compound fu rther comprises contacting the linearly conjugated aryl compo und with a fluoride source. Original
- 26 Canceled
Canceled
2 7. The meth od of claim [[-?6]1, wherein en dc apping the linearly conjugated aryl co m pou n d inte rm ediate occurs prior to the poly ccl ization of the linearly co nju g ated aryl compound to provide a g raphene nan o ribbon precur sor. Currently amended
28 (Currently A m ended) The method of clai m [[26]], wherein e ndeap ping the linearly co nj ugated aryl compound intermediate comprises coupling t h e li n early co 'jugat ed aryl compo und inte rm ediate wi th an aryl m ono m er of form u la (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.10.svg 1.15 1.42 Black and white (VI I) wherein R:4 is hydrogen, fluorine, chlorine, bromine, iodine, lithium, trifluoromeihanesulfnate, m esylate, or t o sylate; and wherein RTh is hydrogen, flu otine, chlorine, bromine, iodine, lithium, tridluoromethanesulf) nate, m esy late, tosylate, bismu th, a bor o nic acid, a bo r onic ester, a boronate ester, an orga n obo rane, an organ o tri fluoroborate, a mag nesium halide, a st anane., a silicon tri h alide, an or g anosilane, an acetylo xy, or a zin c halide. Currently amended
T he m ethod of claim 28, wherein the uns ub stituted rin g carbons on the aryl monomer of fbrmnula VI. are i ndependently sub stit uted with groups selected from hydrogen, hydroxyl, a substit u ted or uns u bstituted (C j-C₂₀)al kyl, (C-20) hydroxyalkyl, (C'~ C₂) alk ox y, (C p-C₂)alklicarboxy, a substituted or unsubstituted aryl., (C 1-Ca)h aloalk vl, (C-~ Ce) alk e nyl, (C₂C)al kynyl, o r an oxo. Previously presented
(C u rrently A m ended) T he method of claim [[26]1 1. wherein e ndeap pin g the linearly co nju gated aryl compound inter m ediate comprises cou pli n g the linearly conjuga t ed ary l compound in termed i ate wi th a 2 -br omoph enyl b oronate, a 2-hl orophenyl boro na te, 2-b romo 1 io dobenzen c, 2-chl o ro- I-io doben zene, o r a combination thereof. Currently amended
The m e thod of clai m [[26 111, wherein end e apping the linearly co rnjugat ed aryl compound intermediate c om prises add i ng a pal ladium ca talys t, a copper salt, an aqueous base, or a c o mbinat io n there of. Currently amended
3 6. (Cu rre ntly Ame n ded) The m ethod of claim [[26]] 1. wherein endcappin g the linearly conjugated aryl c o mpo und intermediate comprises heatin g to a temperature of about 20 C to about 15(0 C for abou t I to about 3 6 hours. Currently amended
Canceled
(Canceled) Canceled
(Origin al) the me thod of cl aim 37, f urther comprising adding a solvent. Original
- 4 3. Canceled
Canceled
- 52. 9 Canceled
Canceled
(Withdrawn-Previously P resented) A method of synt he sizing a gr aphene nanorib bon havi ng a zigzag bac kbone; the metid compnri sin g providing a zigzag con jugat ed aryl comp ound having a formula (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.11.svg 1.39 5.23 Black and white (VI) wherein R 1.and R 3 are indep en dently selected fr om lhydro gen, fluorine, chlorine, b rom ine, iodine, lithium, trifluoromethanesulfbnat, mesyla te, tos ylate, bismuth, a bor onic acid, a boronic ester, a boron ate ester, an o rgan oborane, a n or g anot rifluoroborate, a. ma g ne sium halide, a sta nnane, a silicon t riafide, a org anosilan e, an ac ut yloxy, and a zine halide; wh erein R 2 is hydronge, tr imet hyl silyl, rt-butyl dimeth ylsilyi, te rIbutyldiphenylsilyl, triet hylsilyl, trii sopropylsi lyl, alkyl., phenyl, furanyl, t hiophenyl, pyridyl, or po ly (n-ph enylene) compri s ing about 2 to about 20 tn-ph enyl ene units, wherein R 4 to R.- are independently selected from an alde hyd e group and an acetal group; and po lycyclizing the zigzag conj u gated aryl compou nd t o provi de a graphene na nor ibbon p recurso r. Withdrawn
(Withdrawn-Previo u sly Presented) The me thod o f claim 53, wherein the fi rst aryl monome r has a formula (VII): Respo n se to Non-i-Final Office Action mailed o n September 26, 2 017 SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.12.svg 1.81 1.64 Black and white (VII) w her ein R is hydrogen, t rimethylsilyl, tert-utayldinethylsilyl. tertbtyldiphenyilsilyl, tri ethlyl silyl, triisopropy l sily l, al kyl, phenyl, furanyl, thioph enyl., py ri dy, or po ly (m.-phcny len c) com pris in g about 2 to about 20 m -ph enylene ui ts; wherein R 2 to R; are independently selected from b ydro gen, f l uori n e, chlorine, bromine, i odine, lith i um, trnfluoromethanesutonate, m esylate., tosy l ate, bismu th, a bor o nic a cid, a boro nic ester, a boronate ester, an organ oborane, an org an otri fluorobor ate, a magnesium halide, a stannane, a silicon. tri h alid e, an o rganosilane, an acetyloxy, and a zinc hal i de, w herein at least tw o of R 2 t o R d are not hydro g en; and wherein the second aryl mon omer has a lonm ula. (V III): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.13.svg 0.89 2.23 Black and white (VIII) wherein R 7 and R s are independently selected from hydrogen, fluorine, chlorine, bromine, iodin e, lithium, t rifluorome thanes ulfonate, m esylate, tosylate, bis m uth, a b oron ic acid, a boronic este r, a horonat e ester, an org anobo rane, an or ganotrifl uorobo rate, a magn esium halide, a st a nnan e, a sili con tri hali de, an orgta nosilane, an acet yloxy, and a zi nc halide: and wherein R Q and R m are independently selected from an aldehyde g r oup and an acetal group. Withdrawn
56, (Withdra w n-Previously P res ented The method o f claim 53, frirth er c omp ris ing c oupling a first a ryl monom er and a second aryl mo nomer to pr ovide a zigzag conju gated aryl compoun d i ntermed iate wherein the first aryl mono me r is 2-t rni ethy l sil yl-1,3-d ibo ron ic acid an d the second aryl mono me r is 4,6-bis(bromomethyhisophthaladehyde.
57, (Withdrawn-Previously P resented) The m ethod o f claim 53, wh e rei n c ouplin g a first aryl monomer and a se c ond ary l monomer to provide a zigzag co nju gated aryl compound intermediate comprises contacting the first aryl monomer with the seco n d a ryl monomer in a mola r ra ti o of ab ou t 2:1 to about 1:2. Withdrawn
(Withdrawn-Previously Presented) The m ethod of claim 53, w here in coupling a first aryl monom er and a second aryl monom er to provide a zigza g conjugated aryl compoun d fu rther comprises adding a cataly st. Withdrawn
(Can celed) Canceled
2 59,62. Canceled
Layer stacks claimed or described, ordered top of device to substrate.
organic thin film transistor
Materials described outside the worked examples.
graphene nanoribbon
linearly conjugated aryl compound
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Temperature | 20–120 °C | — |
Duration |
Patent
Atlas literature
Patent
US 10,014,475Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(Currently Amended) A method fo r synt h esizing a g raph ene nanor ibbon, the method c onprising: cou pling a first aryl m ono m er and a second a r y l monomer to provide a linea rly COnTUU gated 4ry compound intennedh ate; end capping the line arl y c onjugated arytl compound intermediate; coupling the lineary cnjugateo try compound intermediate with a mono-subst ituted acetyl eneco.mpo und to p ro vide a line arly conju gat e d ar yl compound h av ing a for mula (B); SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.1.svg 3.03 3.21 Black and white (1) w herei n n is an integer of I to I 00, t)00; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.2.svg 0.22 4.63 Black and white Rs to R, a re i ndep end en tly selected from H, alkyl, aryl, and tri m ethylsily l;[and]] P erf ort ing p olycycl i zatio n of the linearly conj ugated aryl co mpou nd t o provide a gra phene nanco ribbon precursor, wherein perf ormin g polycyclizati o n of the linearly conjugated aryl compound to provide a grap hene nanori bbo n precursor c om prises heatin g to a te m pera ture of about 20 ' C to about 150 * C for ab out I to about 36 hours; and perf i-w ming cyclode hydrogena tion of th e grap hene na noribbon precursor to provide the grap hene nanoribbon, Currently amended
T he method of claim 1, wherein perronin g the cyclodeh y dr o g ena. tion of the gr aphe ne n anoribbon pre cur sor to provide the graphene n anoribbo n comprises performi ng oxidative c ycl ode hyd roge nat ion of the gra phene nan oribbon prec urs or. Previously presented
(Previously Presente d) The method o f claim 1, wh ere in per fornin g the cyc lod ehy drogeu ation of the graphene nanor ibbon precu rs or to provide the graphene na n ori b bon comprises c ontacti ng the gra ph ene nanoribbon precursor with iron (Iii) chloride. Previously presented
(C u rren tl y Amended) A method, f o r synthesizing a ara phen e nan oribb onn the method comprisig, coupling a first aryl monomer and a second ar yl mono m er to provide a linearly on.jugated aryl co mpotmd interm ediat e; coupling the l inearly co n jugat ed aryl compound inte rme diate with a mono- su bst ituted acetylene compound to provid e a linearly conjugated aryl compound h avi n g a fo rmu la (I): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.3.svg 3.03 3.21 Black and white wherein a is an ntcge r of I to 1 09,00 9; SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.4.svg 0.23 4.65 Black and white R to 1 ar e indep ende ntly selected f rom 1I, alkyl, aryl and trimethylsilyl; erforming polcyclizauion of the li early convgaled aryl pomnpQoud to provide a graphene nanorib bon precursor; and p erfor ming cycl dehydrogenation of the gr aphen e n anor ibbon precurs o r to pro yide the raphene noribbon. Currently amended
(Pre v iously Pr esented) The method of claim 2, wherein the first ar yl monomer ha s a formul a (V) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.7.svg 1.59 1.86 Black and white (V) wherein R 1 to R. are indep enden tly selected from h ydrog e n, fluorine, chlorine, bromine, iodi n e, lithium, trifiuorometbanesulfonate, mesy late, t osylat e, bismuth, a b oronic acid, a bo r onic ester, a boronate ester, an organobora ne, an o rgan otrifl uorobo rate, a magnesiu m halide, a stannane, a s ili con triha hide, an org anos ilan e, an. acet y lox y, a n d a zinc halide; and wherein the second a ryl mono mer has a fo rnula (VI) SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.8.svg 1.59 1.99 Black and white (VI) wherein R 7 to R are indep e nde n tly selected from hydrogen, f luorine, chlorine, bro mine, iodine, lithiu m, tifl [oromethanesulftonate, me sylate, tosyl at e, bis m uth, a b oro nic acid, a b oronic ester, a boronate ester, an or gantobora ne, an or gano mtfluoro borat e, a ma gne sium halide, a stannan e, a si lic on t rihal ide, an orga nosil ane. an acetylo xy, and a zin c halide. Previously presented
The method o f claim 2, wherein coupling a first aryl monom er and a second aryl mono m er to provide a linearly c,.jugated iryl compound imterm ediate further comprises heating to a temperature of about 20 C to about 120 C fo r a period of about 1 hour to about 36 hImus. Previously presented
23. (Original) T he m ethod of claim 2 2, furth er c ompr isi ng adding a solvent. Original
The method of clai m 2, whe rein the f irst aryl m onomer is a dihal ophen yl dibo r onate compound and the second ar yl mono mer is a di ha lodiodobenzene compound. Original
IThe meth o d of c llain 2., whe rein c oup lin g a fir s t ar yl monomer and a seco nd aryl monomer to provide a linearly co nju gated aryl co mpound intermediate comprises con tacti ng the first ar yl m onomer with the s ec ond aryl monome r i n a mol ar ratto o f abo ut 2:1 to about 1:2. Original
10, The method of claim 9, wh erein coupling a first ar yl monomer a n d a second aryl m ono mer to provide a linearly c onju gated aryl compound intermediate furth er comprises ad din g a catalyst, Original
- 18. Canceled
Canceled
2 0. The method of clai m 2, further com prising c oup ling the line ar ly conjug ate d aryl c omp ound inte rme diate with a mono-substituted acetylene c o mpo un d to form the linearly c o njugated aryl compound, whe rein the mono-substituted acetyle n e compound has a f ormula (IV): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.9.svg 0.16 1.45 Black and white (IV) wh erei n R n is s e lected f ro m h ydrogen, aryl, polycyclic aryl., alkyl, c opper, zin c, magresium, tin, boron, si lic on, imdium, a luminum, lit hium, sodium, zin c chloride, mercury chloride, mang anese (11) chloride, magnesium bromide, triutyl boron lithium, tributyl aluminum lithi um, dib u tyl a lumin um., trim ethy l silicon, tributy l tin, or b is(cyc l ope n tadien yl)d imethy l zirconium; and R 1 3 is sel ec ted from hydrog en, t rimethy lsilyl, te rt-buty ldi m ethylsilyl, t ert- but y ldip henylsilyl, triethy lsilyl, tri isoprop yls ily l, alkyl, phenyl, f ura nyl, th i opheny l. pyridyl, or poly (m -phenylene) comprising abo u t 2. to about 20 m-pheny lene u n its. Previously presented
21. (Orig in al) The m ethod of claim 20, wherein R i is hydrogen and R is trimethylsilyl. Original
22. (Origin al) The method of cla im 20, wherein co up ling the li ne arly co n jugated aryl compound inter m ediat e with a mono-suhstituted acetylene co mpou nd to f orm the l inea rly conju gated aryl compound fu rther comprises contacting the linearly conjugated aryl compo und with a fluoride source. Original
- 26 Canceled
Canceled
2 7. The meth od of claim [[-?6]1, wherein en dc apping the linearly conjugated aryl co m pou n d inte rm ediate occurs prior to the poly ccl ization of the linearly co nju g ated aryl compound to provide a g raphene nan o ribbon precur sor. Currently amended
28 (Currently A m ended) The method of clai m [[26]], wherein e ndeap ping the linearly co nj ugated aryl compound intermediate comprises coupling t h e li n early co 'jugat ed aryl compo und inte rm ediate wi th an aryl m ono m er of form u la (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.10.svg 1.15 1.42 Black and white (VI I) wherein R:4 is hydrogen, fluorine, chlorine, bromine, iodine, lithium, trifluoromeihanesulfnate, m esylate, or t o sylate; and wherein RTh is hydrogen, flu otine, chlorine, bromine, iodine, lithium, tridluoromethanesulf) nate, m esy late, tosylate, bismu th, a bor o nic acid, a bo r onic ester, a boronate ester, an orga n obo rane, an organ o tri fluoroborate, a mag nesium halide, a st anane., a silicon tri h alide, an or g anosilane, an acetylo xy, or a zin c halide. Currently amended
T he m ethod of claim 28, wherein the uns ub stituted rin g carbons on the aryl monomer of fbrmnula VI. are i ndependently sub stit uted with groups selected from hydrogen, hydroxyl, a substit u ted or uns u bstituted (C j-C₂₀)al kyl, (C-20) hydroxyalkyl, (C'~ C₂) alk ox y, (C p-C₂)alklicarboxy, a substituted or unsubstituted aryl., (C 1-Ca)h aloalk vl, (C-~ Ce) alk e nyl, (C₂C)al kynyl, o r an oxo. Previously presented
(C u rrently A m ended) T he method of claim [[26]1 1. wherein e ndeap pin g the linearly co nju gated aryl compound inter m ediate comprises cou pli n g the linearly conjuga t ed ary l compound in termed i ate wi th a 2 -br omoph enyl b oronate, a 2-hl orophenyl boro na te, 2-b romo 1 io dobenzen c, 2-chl o ro- I-io doben zene, o r a combination thereof. Currently amended
The m e thod of clai m [[26 111, wherein end e apping the linearly co rnjugat ed aryl compound intermediate c om prises add i ng a pal ladium ca talys t, a copper salt, an aqueous base, or a c o mbinat io n there of. Currently amended
3 6. (Cu rre ntly Ame n ded) The m ethod of claim [[26]] 1. wherein endcappin g the linearly conjugated aryl c o mpo und intermediate comprises heatin g to a temperature of about 20 C to about 15(0 C for abou t I to about 3 6 hours. Currently amended
Canceled
(Canceled) Canceled
(Origin al) the me thod of cl aim 37, f urther comprising adding a solvent. Original
- 4 3. Canceled
Canceled
- 52. 9 Canceled
Canceled
(Withdrawn-Previously P resented) A method of synt he sizing a gr aphene nanorib bon havi ng a zigzag bac kbone; the metid compnri sin g providing a zigzag con jugat ed aryl comp ound having a formula (VI): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.11.svg 1.39 5.23 Black and white (VI) wherein R 1.and R 3 are indep en dently selected fr om lhydro gen, fluorine, chlorine, b rom ine, iodine, lithium, trifluoromethanesulfbnat, mesyla te, tos ylate, bismuth, a bor onic acid, a boronic ester, a boron ate ester, an o rgan oborane, a n or g anot rifluoroborate, a. ma g ne sium halide, a sta nnane, a silicon t riafide, a org anosilan e, an ac ut yloxy, and a zine halide; wh erein R 2 is hydronge, tr imet hyl silyl, rt-butyl dimeth ylsilyi, te rIbutyldiphenylsilyl, triet hylsilyl, trii sopropylsi lyl, alkyl., phenyl, furanyl, t hiophenyl, pyridyl, or po ly (n-ph enylene) compri s ing about 2 to about 20 tn-ph enyl ene units, wherein R 4 to R.- are independently selected from an alde hyd e group and an acetal group; and po lycyclizing the zigzag conj u gated aryl compou nd t o provi de a graphene na nor ibbon p recurso r. Withdrawn
(Withdrawn-Previo u sly Presented) The me thod o f claim 53, wherein the fi rst aryl monome r has a formula (VII): Respo n se to Non-i-Final Office Action mailed o n September 26, 2 017 SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.12.svg 1.81 1.64 Black and white (VII) w her ein R is hydrogen, t rimethylsilyl, tert-utayldinethylsilyl. tertbtyldiphenyilsilyl, tri ethlyl silyl, triisopropy l sily l, al kyl, phenyl, furanyl, thioph enyl., py ri dy, or po ly (m.-phcny len c) com pris in g about 2 to about 20 m -ph enylene ui ts; wherein R 2 to R; are independently selected from b ydro gen, f l uori n e, chlorine, bromine, i odine, lith i um, trnfluoromethanesutonate, m esylate., tosy l ate, bismu th, a bor o nic a cid, a boro nic ester, a boronate ester, an organ oborane, an org an otri fluorobor ate, a magnesium halide, a stannane, a silicon. tri h alid e, an o rganosilane, an acetyloxy, and a zinc hal i de, w herein at least tw o of R 2 t o R d are not hydro g en; and wherein the second aryl mon omer has a lonm ula. (V III): SVG 14785323.12-13-2017.JB₅NJJ₄HRXEAPX2.CLM.13.svg 0.89 2.23 Black and white (VIII) wherein R 7 and R s are independently selected from hydrogen, fluorine, chlorine, bromine, iodin e, lithium, t rifluorome thanes ulfonate, m esylate, tosylate, bis m uth, a b oron ic acid, a boronic este r, a horonat e ester, an org anobo rane, an or ganotrifl uorobo rate, a magn esium halide, a st a nnan e, a sili con tri hali de, an orgta nosilane, an acet yloxy, and a zi nc halide: and wherein R Q and R m are independently selected from an aldehyde g r oup and an acetal group. Withdrawn
56, (Withdra w n-Previously P res ented The method o f claim 53, frirth er c omp ris ing c oupling a first a ryl monom er and a second aryl mo nomer to pr ovide a zigzag conju gated aryl compoun d i ntermed iate wherein the first aryl mono me r is 2-t rni ethy l sil yl-1,3-d ibo ron ic acid an d the second aryl mono me r is 4,6-bis(bromomethyhisophthaladehyde.
57, (Withdrawn-Previously P resented) The m ethod o f claim 53, wh e rei n c ouplin g a first aryl monomer and a se c ond ary l monomer to provide a zigzag co nju gated aryl compound intermediate comprises contacting the first aryl monomer with the seco n d a ryl monomer in a mola r ra ti o of ab ou t 2:1 to about 1:2. Withdrawn
(Withdrawn-Previously Presented) The m ethod of claim 53, w here in coupling a first aryl monom er and a second aryl monom er to provide a zigza g conjugated aryl compoun d fu rther comprises adding a cataly st. Withdrawn
(Can celed) Canceled
2 59,62. Canceled
Layer stacks claimed or described, ordered top of device to substrate.
organic thin film transistor
Materials described outside the worked examples.
graphene nanoribbon
linearly conjugated aryl compound
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Temperature | 20–120 °C | — |
Duration |
organic thin film transistor (formula XIV)
organic thin film transistor (formula XV)
first aryl monomer (formula V)
second aryl monomer (formula VI)
dihalophenyl diboronate compound
dihalodiodobenzene compound
mono-substituted acetylene compound (formula IV)
2-trimethylsilyl-1,3-diboronic acid
4,6-bis(bromomethyl)isophthalaldehyde
graphene nanoribbon precursor
iron(III) chloride
FeCl₃
compound of formula XII
compound of formula XIII
compound of formula XIV
compound of formula XV
| — |
Temperature | 20–40 °C | — |
Duration | 1–6 hours | — |
Duration | 6–12 hours | — |
Duration | 12–18 hours | — |
Duration | 18–24 hours | — |
Duration | 24–32 hours | — |
Duration | 32–36 hours | — |
Temperature | 20–150 °C | — |
Temperature | 80–100 °C | — |
Temperature | 100–120 °C | — |
Temperature | 140–150 °C | — |
Thickness | 0.5–7 nm | — |
Thickness | 0.5–5 nm | — |
Thickness | 1.5–6.6 nm | — |
Temperature | 40–60 °C | — |
Duration | ≥ 36 hours | — |
Thickness | ≥ 10 cm | — |
organic thin film transistor (formula XIV)
organic thin film transistor (formula XV)
first aryl monomer (formula V)
second aryl monomer (formula VI)
dihalophenyl diboronate compound
dihalodiodobenzene compound
mono-substituted acetylene compound (formula IV)
2-trimethylsilyl-1,3-diboronic acid
4,6-bis(bromomethyl)isophthalaldehyde
graphene nanoribbon precursor
iron(III) chloride
FeCl₃
compound of formula XII
compound of formula XIII
compound of formula XIV
compound of formula XV
| — |
Temperature | 20–40 °C | — |
Duration | 1–6 hours | — |
Duration | 6–12 hours | — |
Duration | 12–18 hours | — |
Duration | 18–24 hours | — |
Duration | 24–32 hours | — |
Duration | 32–36 hours | — |
Temperature | 20–150 °C | — |
Temperature | 80–100 °C | — |
Temperature | 100–120 °C | — |
Temperature | 140–150 °C | — |
Thickness | 0.5–7 nm | — |
Thickness | 0.5–5 nm | — |
Thickness | 1.5–6.6 nm | — |
Temperature | 40–60 °C | — |
Duration | ≥ 36 hours | — |
Thickness | ≥ 10 cm | — |
organic thin film transistor (formula XIV)
organic thin film transistor (formula XV)
first aryl monomer (formula V)
second aryl monomer (formula VI)
dihalophenyl diboronate compound
dihalodiodobenzene compound
mono-substituted acetylene compound (formula IV)
2-trimethylsilyl-1,3-diboronic acid
4,6-bis(bromomethyl)isophthalaldehyde
graphene nanoribbon precursor
iron(III) chloride
FeCl₃
compound of formula XII
compound of formula XIII
compound of formula XIV
compound of formula XV
| — |
Temperature | 20–40 °C | — |
Duration | 1–6 hours | — |
Duration | 6–12 hours | — |
Duration | 12–18 hours | — |
Duration | 18–24 hours | — |
Duration | 24–32 hours | — |
Duration | 32–36 hours | — |
Temperature | 20–150 °C | — |
Temperature | 80–100 °C | — |
Temperature | 100–120 °C | — |
Temperature | 140–150 °C | — |
Thickness | 0.5–7 nm | — |
Thickness | 0.5–5 nm | — |
Thickness | 1.5–6.6 nm | — |
Temperature | 40–60 °C | — |
Duration | ≥ 36 hours | — |
Thickness | ≥ 10 cm | — |
organic thin film transistor (formula XIV)
organic thin film transistor (formula XV)
first aryl monomer (formula V)
second aryl monomer (formula VI)
dihalophenyl diboronate compound
dihalodiodobenzene compound
mono-substituted acetylene compound (formula IV)
2-trimethylsilyl-1,3-diboronic acid
4,6-bis(bromomethyl)isophthalaldehyde
graphene nanoribbon precursor
iron(III) chloride
FeCl₃
compound of formula XII
compound of formula XIII
compound of formula XIV
compound of formula XV
| — |
Temperature | 20–40 °C | — |
Duration | 1–6 hours | — |
Duration | 6–12 hours | — |
Duration | 12–18 hours | — |
Duration | 18–24 hours | — |
Duration | 24–32 hours | — |
Duration | 32–36 hours | — |
Temperature | 20–150 °C | — |
Temperature | 80–100 °C | — |
Temperature | 100–120 °C | — |
Temperature | 140–150 °C | — |
Thickness | 0.5–7 nm | — |
Thickness | 0.5–5 nm | — |
Thickness | 1.5–6.6 nm | — |
Temperature | 40–60 °C | — |
Duration | ≥ 36 hours | — |
Thickness | ≥ 10 cm | — |