a.Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
cangao@iccas.ac.cn (C.G.)
guanbo@iccas.ac.cn (B.G.)
dhl522@iccas.ac.cn (H.L.D.)
收稿:2022-10-28,
修回:2022-11-27,
录用:2022-12-1,
网络首发:2023-02-01,
纸质出版:2023-08-01
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Liu, Q. Q.; Yang, J. X.; Zhao, M.; Gao, C.; Guan, B.; Dong, H. L. Regioregular asymmetric diketopyrrolopyrrole copolymers with good molecular ordered assembly ability for high-performance polymer transistors. Chinese J. Polym. Sci. 2023, 41, 1215–1222
Qing-Qing Liu, Jia-Xin Yang, Man Zhao, et al. Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1215-1222.
Liu, Q. Q.; Yang, J. X.; Zhao, M.; Gao, C.; Guan, B.; Dong, H. L. Regioregular asymmetric diketopyrrolopyrrole copolymers with good molecular ordered assembly ability for high-performance polymer transistors. Chinese J. Polym. Sci. 2023, 41, 1215–1222 DOI: 10.1007/s10118-023-2918-2.
Qing-Qing Liu, Jia-Xin Yang, Man Zhao, et al. Regioregular Asymmetric Diketopyrrolopyrrole Copolymers with Good Molecular Ordered Assembly Ability for High-performance Polymer Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1215-1222. DOI: 10.1007/s10118-023-2918-2.
Introduction of asymmetric units into conjugated polymers is an important strategy to regulate the photophysical and electronic properties of polymers
as asymmetric units can not only regulate solubility and energy levels
but also molecular stacking and orientation
thus giving much higher optoelectronic properties. However
very few studies have been reported in this field. The semiconducting properties of conjugated polymers could be regulated through regioregularity adjustment. Here
we took the asymmetric thiophene/pyridine side group DPP as core and developed the regioregular monomer T-Py-DPP through three steps: alkyl chain introduction
tin monomer coupling and NBS double bromination. The T-Py-DPP monomer was polymerized into
reg
-PPyTDPP-2FBT with a head-to-head structure. The regioregularity of T-Py-DPP unit endowed
reg
-PPyTDPP-2FBT with backbone planarity
self-assembly orientation
network-like morphology and high crystallinity in films
thus the superior bipolar transport properties. The highest hole and electron mobilities of
reg
-PPyTDPP-2FBT were 0.93 and 0.57 cm
2
·V
−1
·s
−1
respectively
with 40% improvement relative to the regiorandom polymer.
Luo,L.;Huang,W.;Yang,C.;Zhang,J.;Zhang,Q.Recentadvanceson π -conjugatedpolymersasactiveelementsinhighperformanceorganicfield-effecttransistors. Front. Phys. 2021 , 16 ,33500..
Yao,Z.F.;Li,Q.Y.;Wu,H.T.;Ding,Y.F.;Wang,Z.Y.;Lu,Y.;Wang,J.Y.;Pei,J.BuildingcrystalstructuresofconjugatedpolymersthroughX-raydiffractionandmolecularmodeling. SmartMat 2021 , 2 ,378−387..
Zhou,Y.;Zhang,W.;Yu,G.Recentstructuralevolutionoflactam-andimide-functionalizedpolymersappliedinorganicfield-effecttransistorsandorganicsolarcells. Chem. Sci. 2021 , 12 ,6844−6878..
Adachi,C.;Sandanayaka,A.S.D.TheleapfromOrganiclight-emittingdiodestoorganicsemiconductorlaserdiodes. CCS Chem. 2020 , 2 ,1203−1216..
He,M.N.;Zhao,Y.;Liu,Y.Q.;Wei,D.C.A3Dprintableself-healingcompositeconductivepolymerforsensitivetemperaturedetection. Chin. Chem. Lett. 2020 , 31 ,826−830..
Yang,Y.Multi-tiercomputingnetworksforintelligentIoT. Nat. Electron. 2019 , 2 ,4−5..
Ni,Z.j.;Dong,H.L.;Wang,H.L.;Ding,S.;Zou,Y.;Zhao,Q.;Zhen,Y.G.;Liu,F.;Jiang,L.;Hu.W.P.Quinoline-flankeddiketopyrrolopyrrolecopolymersbreakingthroughelectronmobilityover6cm 2 V −1 s −1 inflexiblethinfilmdevices. Adv. Mater. 2018 , 30 ,1704843..
Yang,J.;Wang,H.;Chen,J.;Huang,J.;Jiang,Y.;Zhang,J.;Shi,L.;Sun,Y.;Wei,Z.;Yu,G.;Guo,Y.;Wang,S.;Liu,Y.Bis-diketopyrrolopyrrolemoietyasapromisingbuildingblocktoenablebalancedambipolarpolymersforflexibletransistors. Adv. Mater. 2017 , 29 ,1606162..
Yi,Z.;Wang,S.;Liu,Y.Designofhigh-mobilitydiketopyrrolopyrrole- b based π -conjugatedcopolymersfororganicthin-filmtransistors. Adv. Mater. 2015 , 27 ,3589−3606..
Ma,J.;Tian,J.;Liu,Z.;Shi,D.;Zhang,X.;Zhang,G.;Zhang,D.Multi-stimuli-responsivefield-effecttransistorwithconjugatedpolymerentailingspiropyraninthesidechains. CCS Chem. 2020 , 2 ,632−641..
Xu,J.;Wang,S.H.;Wang,G.J.N.;Zhu,C.X.;Luo,S.C.;Jin,L.H.;Gu,X.D.;Chen,S.C.;Feig,V.R.;To,J.W.F.;Rondeau-Gagne,S.;Park,J.;Schroeder,B.C.;Lu,C.;Oh,J.Y.;Wang,Y.M.;Kim,Y.H.;Yan,H.;Sinclair,R.;Zhou,D.S.;Xue,G.;Murmann,B.;Linder,C.;Cai,W.;Tok,J.B.H.;Chung,J.W.;Bao,Z.N.Highlystretchablepolymersemiconductorfilmsthroughthenanoconfinementeffect. Science 2017 , 355 ,59−64..
Qin,Z.S.;Gao,H.K.;Dong,H.L.;Hu,W.P.Organiclight-emittingtransistorsenteringanewdevelopmentstage. Adv. Mater. 2021 , 33 ,2007149..
Huang,F;Bo,Z.S;Geng,Y.H.;Wang,X.H.;Wang,L.X.;Ma,Y.G.;Hou,J.H.;Hu,W.P.;Pei,J.;Dong,H.L.;Wang,S.;Li,Z;Shuai,Z.G.;Li,Y.F.;Cao,Y.Studyonoptoelectronicpolymers:anoverviewandoutlook. Acta Polymerica Sinica (inChinese) 2019 , 50 ,988−1046..
Zhao,R.Y.;Liu,J.;Wang,L.X.PolymeracceptorscontainingB◊Nunitsfororganicphotovoltaics. Acc. Chem. Res. 2020 , 53 ,1557−1567..
Yue,H.;Wang,Z.;Zhen,Y.Recentadvancesofself-healingelectronicmaterialsappliedinorganicfield-effecttransistors. ACS Omega 2022 , 7 ,18197−18205..
Miao,J.;Wang,Y.;Liu,J.;Wang,L.Organoboronmoleculesandpolymersfororganicsolarcellapplications. Chem. Soc. Rev. 2022 , 51 ,153−187..
Yao,Z.F.;Zheng,Y.Q.;Dou,J.H.;Lu,Y.;Ding,Y.F.;Ding,L.;Wang,J.Y.;Pei,J.Approachingcrystalstructureandhighelectronmobilityinconjugatedpolymercrystals. Adv. Mater. 2021 , 33 ,e2006794..
Yu,Z.D.;Lu,Y.;Wang,J.Y.;Pei,J.Conformationcontrolofconjugatedpolymers. Chemistry 2020 , 26 ,16194−16205..
Wu,Y.J.;Zhao,Y.;Liu,Y.Q.Towardefficientchargetransportofpolymer-basedorganicfield-effecttransistors:moleculardesign,processing,andfunctionalutilization. Acc. Chem. Res. 2021 , 2 ,1047−1058..
Wang,M.;Ford,M.;Phan,H.;Coughlin,J.;Nguyen,T.Q.;Bazan,G.C.Fluorinesubstitutioninfluenceonbenzo[2,1,3]thiadiazolebasedpolymersforfield-effecttransistorapplications. Chem. Commun. 2016 , 52 ,3207−3210..
Yu,Y.;Wu,Y.;Zhang,A.;Li,C.;Tang,Z.;Ma,W.;Wu,Y.;Li,W.Diketopyrrolopyrrolepolymerswiththienylandthiazolyllinkersforapplicationinfield-effecttransistorsandpolymersolarcells. ACS Appl. Mater. Interfaces 2016 , 8 ,30328−30335..
Hu,D.P.;Chen,M.;Yang,Y.H.;Li,H.Y.Textureinducedbymolecularweightdispersity:polymorphismwithinpoly(L-lacticacid)spherulites. Chinese J. Polym. Sci. 2020 , 38 ,1365−1373..
Qiu,G.G.;Ni,Z.J.;Wang,H.L.;Dong,H.L.;Zhang,J.Q.;Zhang,X.T.;Shu,Z.B.;Lu,K.;Zhen,Y.G.;Wei,Z.X.;Hu,W.P.Asymmetricthiophene/pyridineflankeddiketopyrrolopyrrolepolymersforhighperformancepolymerambipolarfield-effecttransistorsandsolarcells. J. Mater. Chem. C 2017 , 5 ,566−572..
Fan,B.;Li,M.;Zhang,D.;Zhong,W.;Ying,L.;Zeng,Z.;An,K.;Huang,Z.;Shi,L.;Bazan,G.C.;Huang,F.;Cao,Y.Tailoringregioisomericstructuresof π -conjugatedpolymerscontainingmonofluorinated π -bridgesforhighlyefficientpolymersolarcells. ACS Energy Lett. 2020 , 5 ,2087−2094..
Yen,H.C.;Lin,Y.C.;Chen,W.C.Modulationofthehydrophilicityonasymmetricsidechainsofisoindigo-basedpolymersforimprovingcarriermobility-stretchabilityproperties. Macromolecules 2021 , 54 ,1665−1676..
Ji,Y.;Xiao,C.;Wang,Q.;Zhang,J.;Li,C.;Wu,Y.;Wei,Z.;Zhan,X.;Hu,W.;Wang,Z.;Janssen,R.A.;Li,W.Asymmetricdiketopyrrolopyrroleconjugatedpolymersforfield-effecttransistorsandpolymersolarcellsprocessedfromanonchlorinatedsolvent. Adv. Mater. 2016 , 28 ,943−950..
Gao,W.;Zhang,M.;Liu,T.;Ming,R.;An,Q.;Wu,K.;Xie,D.;Luo,Z.;Zhong,C.;Liu,F.;Zhang,F.;Yan,H.;Yang,C.Asymmetricalladder-typedonor-inducedpolarsmallmoleculeacceptortopromotefillfactorsapproaching77%forhigh-performancenonfullerenepolymersolarcells. Adv. Mater. 2018 , 30 ,1800052..
Zhong,W.;Sun,S.;Ying,L.;Liu,F.;Lan,L.;Huang,F.;Cao,Y.High-performanceorganicfield-effecttransistorsfabricatedbasedonanovelternarypi-conjugatedcopolymer. ACS Appl. Mater. Interfaces 2017 , 9 ,7315−7321..
Cho,Y.;Park,S.;Jeong,S.;Yang,H.;Lee,B.;Lee,S.M.;Lee,B.H.;Yang,C.Regioregular,yetductileandamorphousindacenodithiophene-basedpolymerswithhigh-mobilityforstretchableplastictransistors. J. Mater. Chem. C 2021 , 9 ,9670−9682..
Huang,Y.;Zheng,N.;Wang,Z.;Ying,L.;Huang,F.;Cao,Y.Synthesisofregioregular π -conjugatedpolymersconsistingofalactammoiety via directheteroarylationpolymerization. Chem. Commun. 2017 , 53 ,1997−2000..
Leenaers,P.J.;vanEersel,H.;Li,J.;Wienk,M.M.;Janssen,R.A.J.InfluenceofregioregularityontheoptoelectronicpropertiesofconjugateddiketopyrrolopyrrolepolymerscomprisingasymmetricMonomers. Macromolecules 2020 , 53 ,7749−7758..
Zhong,H.;Li,C.Z.;Carpenter,J.;Ade,H.;Jen,A.K.Influenceofregio-andchemoselectivityonthepropertiesoffluoro-substitutedthienothiopheneandbenzodithiophenecopolymers. J. Am. Chem. Soc. 2015 , 137 ,7616−7619..
Kim,Y.;Cook,S.;Tuladhar,S.M.;Choulis,S.A.;Nelson,J.;Durrant,J.R.;Bradley,D.D.C.;Giles,M.;McCulloch,I.;Ha,C.S.;Ree,M.Astrongregioregularityeffectinself-organizingconjugatedpolymerfilmsandhigh-efficiencypolythiophene:fullerenesolarcells. Nat. Mater. 2006 , 5 ,197−203..
Sirringhaus,H.;Brown,P.J.;Friend,R.H.;Nielsen,M.M.;Bechgaard,K.;Langeveld-Voss,B.M.W.;Spiering,A.J.H.;Janssen,R.A.J.;Meijer,E.W.;Herwig,P.;deLeeuw,D.M.Two-dimensionalchargetransportinself-organized,high-mobilityconjugatedpolymers. Nature 1999 , 401 ,685−688..
Coughlin,J.E.;Zhugayevych,A.;Wang,M.;Bazan,G.C.;Tretiak,S.Chargedelocalizationcharacteristicsofregioregularhighmobilitypolymers. Chem. Sci. 2017 , 8 ,1146−1151..
Perez,L.A.;Zalar,P.;Ying,L.;Schmidt,K.;Toney,M.F.;Nguyen,T.Q.;Bazan,G.C.;Kramer,E.J.Effectofbackboneregioregularityonthestructureandorientationofadonor-acceptorsemiconductingcopolymer. Macromolecules 2014 , 47 ,1403−1410..
Yang,J.X.;Liu,Q.Q.;Hu,M.X.;Ding,S.;Liu,J.;Wang,Y.S.;Liu,D.;Gao,H.K.;Hu,W.P.;Dong,H.L.Well-balancedambipolardiketopyrrolopyrrole-basedcopolymersforOFETs,invertersandfrequencydoublers. Sci. China Chem. 2021 , 64 ,1410−1416..
Ding,S.;Ni,Z.J.;Hu,M.X.;Qiu,G.G.;Li,J.;Ye,J.;Zhang,X.T.;Liu,F.;Dong,H.L.;Hu,W.P.Anasymmetricfuran/thieno[3,2- b ]thiophenediketopyrrolopyrrolebuildingblockforannealing-freegreensolventprocessableorganicthin-filmtransistors. Macromol. Rapid Commun. 2018 , 39 ,1800225..
Aoshima,K.;Nomura,M.;Saeki,A.Regioregularityandelectrondeficiencycontrolofunsymmetricdiketopyrrolopyrrolecopolymersfororganicphotovoltaics. ACS Omega 2019 , 4 ,15645−15652..
Ying,L.;Hsu,B.B.;Zhan,H.;Welch,G.C.;Zalar,P.;Perez,L.A.;Kramer,E.J.;Nguyen,T.Q.;Heeger,A.J.;Wong,W.Y.;Bazan,G.C.Regioregularpyridal[2,1,3]thiadiazole π -conjugatedcopolymers. J. Am. Chem. Soc. 2011 , 133 ,18538−18541..
Wang,Z.Y.;DiVirgilio,L.;Yao,Z.F.;Yu,Z.D.;Wang,X.Y.;Zhou,Y.Y.;Li,Q.Y.;Lu,Y.;Zou,L.;Wang,H.I.;Wang,X.Y.;Wang,J.Y.;Pei,J.Correlatingchargetransportpropertiesofconjugatedpolymersinsolutionaggregatesandthin-filmaggregates. Angew. Chem. Int. Ed. 2021 , 60 ,20483−20488..
Rivnay,J.M.S.C.;Miller,C.E.;Salleo,A.;Toney,M.F.Quantitativedeterminationoforganicsemiconductormicrostructurefromthemoleculartodevicescale. Chem. Rev. 2012 , 112 ,5488−5519..
Ni,Z.J;Wang,H.L.;Zhao,Q.;Zhang,J.Q.;Wei,Z.X.;Dong,H.L.;Hu,W.P.Ambipolarconjugatedpolymerswithultrahighbalancedholeandelectronmobilityforprintedorganiccomplementarylogic via atwo-stepC-Hactivationstrategy. Adv. Mater. 2019 , 31 ,e1806010..
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