

FOLLOWUS
a.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China
b.School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
xlqiao@dhu.edu.cn (X.L.Q.)
zmf@dhu.edu.cn (M.F.Z.)
Received:03 May 2023,
Revised:2023-7-14,
Accepted:31 July 2023,
Online First:15 September 2023,
Published:01 January 2024
Scan QR Code
Liu, H. Y.; Han, L. H.; Kong, L. W.; Zhu, L. P.; Qiao, X. L.; Zhu, M. F. Poly(3-hexylthio) thiophene field-effect transistor device performance: impact of the content of hexylthio side chain on backbone. Chinese J. Polym. Sci. 2024, 42, 14–23
Hao-Yu Liu, Lian-He Han, Ling-Wei Kong, et al. Poly(3-hexylthio) thiophene Field-effect Transistor Device Performance: Impact of the Content of Hexylthio Side Chain on Backbone[J]. Chinese Journal of Polymer Science, 2024, 42(1): 14-23.
Liu, H. Y.; Han, L. H.; Kong, L. W.; Zhu, L. P.; Qiao, X. L.; Zhu, M. F. Poly(3-hexylthio) thiophene field-effect transistor device performance: impact of the content of hexylthio side chain on backbone. Chinese J. Polym. Sci. 2024, 42, 14–23 DOI: 10.1007/s10118-023-3042-z.
Hao-Yu Liu, Lian-He Han, Ling-Wei Kong, et al. Poly(3-hexylthio) thiophene Field-effect Transistor Device Performance: Impact of the Content of Hexylthio Side Chain on Backbone[J]. Chinese Journal of Polymer Science, 2024, 42(1): 14-23. DOI: 10.1007/s10118-023-3042-z.
Studying the effect of hexylthio chain content on poly (3-hexylthio)thiophene crystallization
aggregation
and optoelectronic performance of OFET devices by modulating the content of thiohexyl chains on the main chain.
Regioregular poly(3-hexylthio)thiopene (
P3HTT
) has emerged tremendous potential in organic electronic applications due to the strong noncovalent interactions from the sulfur atom linked to thiophene. However
P3HTT
generally exhibits low charge mobility mostly due to poor solution processability attributed to dense arrangement of hexylthio side chain in polymer
which led to strong noncovalent interactions among sulfur atoms. To balance the nonvalent interaction and aggregation for
P3HTT
herein
we systematically study the effect of hexylthio side chain content in polymer backbone on the structure and properties. A series of regioregular
P3HTT
-based homopolymers (
P3HTT
P3HTT-50
P3HTT-33
and
P3HTT-25
) were prepared
via
Kumada catalyst transfer polycondensation method from a set of mono-
bi-
ter- and quarter- thiophenes containing different contents of hexylthio side chain. The DFT calculation shows the planarity of polymers backbone could be improved through reducing the density of hexylthio side chain in polymer mainchain. And significant changes in their crystallinity
aggregation and optical properties were observed with the content of hexylthio side chain reducing. The
P3HTT-33
displayed the highest field-effect transistor hole mobility of 2.83×10
−2
cm
2
·V
−1
·s
−1
resulting from a balance between the crystallinity and planarity. This study demonstrates modulating the content of hexylthio side chain in
P3HTT
is an effective strategy to optimize the opto-electronic properties of polymer obtaining excellent semiconductor device performance.
Wang,C.;Zhang,X.T.;Dong,H.L.;Chen,X.D.;Hu,W.P.Challengesandemergingopportunitiesinhigh-mobilityandlow-energy-consumptionorganicfield-effecttransistors. Adv. Energy Mater. 2020 , 10 ,2000955..
Sirringhaus,H.25 th Anniversaryarticle:organicfield-effecttransistors:thepathbeyondamorphoussilicon. Adv. Mater. 2014 , 26 ,1319−1335..
Yang,J.;Zhao,Z.;Wang,S.;Guo,Y.;Liu,Y.Insightintohigh-performanceconjugatedpolymersfororganicfield-effecttransistors. Chem 2018 , 4 ,2748−2785..
Wang,Y.;Hasegawa,T.;Matsumoto,H.;Michinobu,T.Significantimprovementofunipolarn-typetransistorperformancesbymanipulatingthecoplanarbackboneconformationofelectron-deficientpolymers via hydrogenbonding. J. Am. Chem. Soc. 2019 , 141 ,3566−3575..
Wu,W.N.;Tu,T.H.;Pai,C.H.;Cheng,K.H.;Tung,S.H.;Chan,Y.T.;Liu,C.L.Metallo-supramolecularrod-coilblockcopolymerthinfilmsforstretchableorganicfieldeffecttransistorapplication. Macromolecules 2022 , 55 ,10670–10681..
Hou,J.;Inganäs,O.;Friend,R.H.;Gao,F.Organicsolarcellsbasedonnon-fullereneacceptors. Nat. Mater. 2018 , 17 ,119−128..
Huang,Y.;Kramer,E.J.;Heeger,A.J.;Bazan,G.C.Bulkheterojunctionsolarcells:morphologyandperformancerelationships. Chem. Rev. 2014 , 114 ,7006−7043..
Xu,X.;Li,Z.;Bi,Z.;Yu,T.;Ma,W.;Feng,K.;Li,Y.;Peng,Q.Highlyefficientnonfullerenepolymersolarcellsenabledbyacopper(I)coordinationstrategyemployinga1,3,4-oxadiazole-containingwide-bandgapcopolymerdonor. Adv. Mater. 2018 , 30 ,1800737..
Yuan,J.;Zhang,Y.;Zhou,L.;Zhang,G.;Yip,H.L.;Lau,T.K.;Lu,X.;Zhu,C.;Peng,H.;Johnson,P.A.;Leclerc,M.;Cao,Y.;Ulanski,J.;Li,Y.;Zou,Y.Single-junctionorganicsolarcellwithover15%efficiencyusingfused-ringacceptorwithelectron-deficientcore. Joule 2019 , 3 ,1140−1151..
Tao,Y.;Yuan,K.;Chen,T.;Xu,P.;Li,H.;Chen,R.;Zheng,C.;Zhang,L.;Huang,W.Thermallyactivateddelayedfluorescencematerialstowardsthebreakthroughoforganoelectronics. Adv. Mater. 2014 , 26 ,7931−7958..
Uoyama,H.;Goushi,K.;Shizu,K.;Nomura,H.;Adachi,C.Highlyefficientorganiclight-emittingdiodesfromdelayedfluorescence. Nature 2012 , 492 ,234−238..
Shin,K.;Lee,E.;Lee,T.;Lee,Y.H.;Kim,D.H.;Kim,C.;Jung,J.;Jung,B.J.;Lee,M.H.EfficientTADFfromcarbon-carbonbondeddonor-acceptormoleculesbasedonboron-carbonylhybridacceptor. Dyes Pigments 2023 , 209 ,110937..
Chen,X.K.;Kim,D.;Brédas,J.L.Thermallyactivateddelayedfluorescence(TADF)pathtowardefficientelectroluminescenceinpurelyorganicmaterials:molecularlevelinsight. Acc. Chem. Res. 2018 , 51 ,2215−2224..
Yang,Y.;Liu,Z.;Zhang,G.;Zhang,X.;Zhang,D.Theeffectsofsidechainsonthechargemobilitiesandfunctionalitiesofsemiconductingconjugatedpolymersbeyondsolubilities. Adv. Mater. 2019 , 31 ,1903104..
Liu,C.;Wang,K.;Gong,X.;Heeger,A.J.Lowbandgapsemiconductingpolymersforpolymericphotovoltaics. Chem. Soc. Rev. 2016 , 45 ,4825−4846..
Gumyusenge,A.;Tran,D.T.;Luo,X.;Pitch,G.M.;Zhao,Y.;Jenkins,K.A.;Dunn,T.J.;Ayzner,A.L.;Savoie,B.M.;Mei,J.G.Semiconductingpolymerblendsthatexhibitstablechargetransportathightemperatures. Science 2018 , 362 ,1131-1134..
Tanwar,A.S.;Mehtab,M.;Kim,J.T.;Oh,K.J.;Iyer,P.K.;Im,Y.H.Real-timeselectivepesticidedetectionusingcatalyticbehaviorofzwitterionicconjugatedpolymer. Chem. Eng. J. 2023 , 456 ,141002..
Yang,J.;Kang,F.;Wang,X.;Zhang,Q.Designstrategiesforimprovingthecrystallinityofcovalentorganicframeworksandconjugatedpolymers:areview, Mater. Horiz. 2022 , 9 ,121−146..
Yuan,Z.;Buckley,C.;Thomas,S.;Zhang,G.;Bargigia,I.;Wang,G.;Fu,B.;Silva,C.;Brédas,J.L.;Reichmanis,E.Athiazole-naphthalenediimidebasedn-channeldonor-acceptorconjugatedpolymer. Macromolecules 2018 , 51 ,7320–7328..
Shi,Y.;Li,W.;Wang,X.;Tu,L.;Li,M.;Zhao,Y.;Wang,Y.;Liu,Y.Isomericacceptor-acceptorpolymers:enablingelectrontransportwithstrikinglydifferentsemiconductingpropertiesinn-channelorganicthin-filmtransistors. Chem. Mater. 2022 , 34 ,1403−1413..
Wei,C.;Zhang,W.;Huang,J.;Li,H.;Zhou,Y.;Yu,G.Realizingn-typefield-effectperformance via introducingtrifluoromethylgroupsintothedonor-acceptorcopolymerbackbone. Macromolecules 2019 , 52 ,2911−2921..
Kim,H.;Lee,J.;Kim,T.;Cho,M.;Choi,T.L.Precisionsynthesisofvariouslow-bandgapdonor-acceptoralternatingconjugatedpolymers via livingSuzuki-Miyauracatalyst-transferpolymerization. Angew. Chem. 2022 , 134 ,e202205828..
Janus,K.;Chlebosz,D.;Janke,A.;Goldman,W.;Kiersnowski,A.Contributionsofpolymerchainlength,aggregationandcrystallinitydegreesinamodelofchargecarriertransportinultrathinpolymerfilms. Macromolecules 2023 , 56 ,964−973..
Park,Y.D.;Kim,D.H.;Jang,Y.;Cho,J.H.;Hwang,M.;Lee,H.S.;Lim,J.A.;Cho,K.Effectofsidechainlengthonmolecularorderingandfield-effectmobilityinpoly(3-alkylthiophene)transistors. Org. Electron. 2006 , 7 ,514−520..
Son,S.Y.;Park,T.;You,W.Understandingofface-oncrystallitestransitioningtoedge-oncrystallitesinthiophene-basedconjugatedpolymers. Chem. Mater . 2021 , 33 ,4541−4550..
Schmode,P.;Schötz,K.;Dolynchuk,O.;Panzer,F.;Köhler,A.;Thurn-Albrecht,T.;Thelakkat,M.Influenceof ω -bromosubstitutiononstructureandoptoelectronicpropertiesofhomopolymersandgradientcopolymersof3-hexylthiophene. Macromolecules 2020 , 53 ,2474−2484..
Zhang,L.;Colella,N.S.;Cherniawski,B.P.;Mannsfeld,S.C.B.;Briseno,A.L.Oligothiophenesemiconductors:synthesis,characterization,andapplicationsfororganicdevices. ACS Appl. Mater. Interfaces 2014 , 6 ,5327−5343..
Nielsen,C.B.;McCulloch,I.Recentadvancesintransistorperformanceofpolythiophenes. Prog. Polym. Sci. 2013 , 38 ,2053−2069..
Mishra,A.;Ma,C.Q.;Bauerle,P.Functionaloligothiophenes:moleculardesignformultidimensionalnanoarchitecturesandtheirapplications. Chem. Rev. 2009 , 109 ,1141−1276..
Okamoto,K.;Luscombe,C.K.Controlledpolymerizationsforthesynthesisofsemiconductingconjugatedpolymers. Polym. Chem. 2011 , 2 ,2424−2434..
McCullough,R.D.;Lowe,R.D.Enhancedelectricalconductivityinregioselectivelysynthesizedpoly(3-alkylthiophenes). J. Chem. Soc., Chem. Commun . 1992 ,70-72..
McCullough,R.D.;Lowe,R.D.;Jayaraman,M.;Anderson,D.L.Design,synthesis,andcontrolofconductingpolymerarchitectures:structurallyhomogeneouspoly(3-alkylthiophenes). J. Org. Chem. 1993 , 58 ,904−912..
Chen,T.A.;Rieke,R.D.Thefirstregioregularhead-to-tailpoly(3-hexylthiophene-2,5-diyl)andaregiorandomisopolymer:nickelversuspalladiumcatalysisof2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophenepolymerization. J. Am. Chem. Soc. 1992 , 114 ,10087−10088..
Chen,T.A.;Wu,X.;Rieke,R.D.Regiocontrolledsynthesisofpoly(3-alkylthiophenes)mediatedbyriekezinc:theircharacterizationandsolid-stateproperties. J. Am. Chem. Soc. 1995 , 117 ,233−244..
Persson,N.E.;Chu,P.H.;McBride,M.;Grover,M.;Reichmanis,E.Nucleation,growth,andalignmentofpoly(3-hexylthiophene)nanofibersforhigh-performanceOFETs. Acc. Chem. Res. 2017 , 50 ,932−942..
Yokoyama,A.;Miyakoshi,R.;Yokozawa,T.Chain-growthpolymerizationforpoly(3-hexylthiophene)withadefinedmolecularweightandalowpolydispersity. Macromolecules 2004 , 37 ,1169−1171..
Iovu,M.C.;Sheina,E.E.;Gil,R.R.;McCullough,R.D.Experimentalevidenceforthequasi-“living”natureofthegrignardmetathesismethodforthesynthesisofregioregularpoly(3-alkylthiophenes). Macromolecules 2005 , 38 ,8649−8656..
Chang,J.F.;Sun,B.;Breiby,D.W.;Nielsen,M.M.;Sölling,T.I.;Giles,M.;McCulloch,I.;Sirringhaus,H.Enhancedmobilityofpoly(3-hexylthiophene)transistorsbyspin-coatingfromhigh-boiling-pointsolvents. Chem. Mater. 2004 , 16 ,4772−4776..
Li,G.;Shrotriya,V.;Huang,J.;Yao,Y.;Moriarty,T.;Emery,K.;Yang,Y.High-efficiencysolutionprocessablepolymerphotovoltaiccellsbyself-organizationofpolymerblends. Nat. Mater. 2005 , 4 ,864−868..
Fei,Z.;Boufflet,P.;Wood,S.;Wade,J.;Moriarty,J.;Gann,E.;Ratcliff,E.L.;McNeill,C.R.;Sirringhaus,H.;Kim,J.S.;Heeney,M.Influenceofbackbonefluorinationinregioregularpoly(3-alkyl-4-fluoro)thiophenes. J. Am. Chem. Soc. 2015 , 137 ,6866−6879..
Blaskovits,J.T.;Bura,T.;Beaupré,S.;Lopez,S.A.;Roy,C.;Soares,J.G.;Oh,A.;Quinn,J.;Li,Y.;Aspuru-Guzik,A.;Leclerc,M.Astudyofthedegreeoffluorinationinregioregularpoly(3-hexylthiophene). Macromolecules 2017 , 50 ,162−174..
GianluigiA.;GennaroP.;LorenzoD.B.Chiropticalpropertiesinthinfilmsof π -conjugatedsystems. Chem. Rev. 2020 , 120 ,10145−10243..
Huo,L.;Zhou,Y.;Li,Y.Alkylthio-substitutedpolythiophene:absorptionandphotovoltaicproperties. Macromol. Rapid Commun. 2009 , 30 ,925−931..
Vegiraju,S.;Chang,B.C.;Priyanka,P.;Huang,D.Y.;Wu,K.Y.;Li,L.H.;Chang,W.C.;Lai,Y.Y.;Hong,S.H.;Yu,B.C.;Wang,C.L.;Chang,W.J.;Liu,C.L.;Chen,M.C.;Facchetti,A.Intramolecularlockeddithioalkylbithiophene-basedsemiconductorsforhigh-performanceorganicfield-effecttransistors. Adv. Mater. 2017 , 29 ,1702414..
Vegirju,S.;Luo,X.L.;Li,L.H.;Afraj,S.N.;Lee,C.;Zheng,D.;Hsieh,H.C.;Lin,C.C.;Hong,S.H.;Tsai,H.C.;Lee,G.H.;Tung,S.H.;Liu,C.L.;Chen,M.C.;Facchett,A.Solutionprocessablepseudon-thienoacenes via intramolecularS···SLockforhighperformanceorganicfieldeffecttransistors. Chem. Mater. 2020 , 32 ,1422−1429..
Vegiraju,S.;Torimtubun,A.A.A.;Lin,P.S.;Tsai,H.C.;Lien,W.C.;Chen,C.S.;He,G.Y.;Lin,C.Y.;Zheng,D.;Huang,Y.F.;Wu,Y.C.;Yau,S.L.;Lee,G.H.;Tung,S.H.;Wang,C.L.;Liu,C.L.;Chen,M.C.;Facchetti,A.Solution-processablequinoidaldithioalkylterthiophene-basedsmallmoleculespseudo-pentathienoacenes via anintramolecularS···Slockforhigh-performancen-typeorganicfield-effecttransistors. ACS Appl. Mater. Interfaces 2020 , 12 ,25081−25091..
Shi,S.;Wang,H.;Uddin,M.A.;Yang,K.;Su,M.;Bianchi,L.;Chen,P.;Cheng,X.;Guo,H.;Zhang,S.;Woo,H.Y.;Guo,X.Head-to-headlinkeddialkylbifuran-basedpolymersemiconductorsforhigh-performanceorganicthin-filmtransistorswithtunablechargecarrierpolarity. Chem. Mater. 2019 , 31 ,1808−1817..
Wu,X.;Chen,T.A.;Rieke,R.D.Astudyofsmallbandgappolymers:head-to-tailregioregularpoly[3-(alkylthio)thiophenes]preparedbyregioselectivesynthesisusingactivezinc. Macromolecules 1996 , 29 ,7671−7677..
Vandeleene,S.;Bergh,K.V.;Verbiest,T.Koeckelberghs,G.Influenceofthepolymerizationmethodologyontheregioregularityandchiropticalpropertiesofpoly(alkylthiothiophene)s. Macromolecules 2008 , 41 ,5123−5131..
Krasovskiy,A.;Krasovskaya,V.;Knochel,P.MixedMg/LiamidesofthetypeR2NMgCl·LiClashighlyefficientbasesfortheregioselectivegenerationoffunctionalizedarylandheteroarylmagnesiumcompounds. Angew. Chem. Int. Ed. 2006 , 45 ,2958−2961..
Lin,P.S.;Shoji,Y.;Afraj,S.N.;Ueda,M.;Lin,C.H.;Inagaki,S.;Endo,T.;Tung,S.H.;Chen,M.C.;Liu,C.L.;Higashihara,T.Controlledsynthesisofpoly[(3-alkylthio)thiophene]sandtheirapplicationtoorganicfield-effecttransistors. ACS Appl. Mater. Interfaces 2021 , 13 ,31898−31909..
Maria,F.D.;Olivelli,P.;Gazzano,M.;Zanelli,A.;Biasiucci,M.;Gigli,G.;Gentili,D.;D’Angelo,P.;Cavallini,M.;Barbarella,G.Asuccessfulchemicalstrategytoinduceoligothiopheneself-assemblyintofiberswithtunableshapeandfunction. J. Am. Chem. Soc. 2011 , 133 ,8654−8661..
Chen,C.A.;Yang,P.C.;Wang,S.C.;Tung,S.H.;Su,W.F.Sidechaineffectsontheoptoelectronicpropertiesandself-assemblybehaviorsofterthiophene–thieno[3,4- c ]pyrrole-4,6-dionebasedconjugatedpolymers. Macromolecules 2018 , 51 ,7828–7835..
Clark,J.;Chang,J.F.;Spano,F.C.;Friend,R.H.;Silva,C.Determiningexcitonbandwidthandfilmmicrostructureinpolythiophenefilmsusinglinearabsorptionspectroscopy Appl. Phys. Lett . 2009 , 94 ,163306..
Qiao,X.L.;Yang,J.;Han,L.H.;Zhang,J.D.;Zhu,M.F.Synergisticeffectsofsolventvaporassistedspin-coatingandthermalannealingonenhancingthecarriermobilityofpoly(3-hexylthiophene)field-effecttransistors. Chinese J. Polym. Sci. 2021 , 39 ,849−855..
0
Views
190
Downloads
0
CSCD
Publicity Resources
Related Articles
Related Author
Related Institution
京公网安备11010802046900号