Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors

Yi-Fan Li; Yun-Long Guo; Yun-Qi Liu

doi:10.1007/s10118-023-2952-0

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Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors

REVIEW | Updated：2023-04-21

- Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors
- Chinese Journal of Polymer Science Vol. 41, Issue 5, Pages: 652-670(2023)
- Affiliations：
  
  a.Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  b.University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  guoyunlong@iccas.ac.cn(Y.L.G.)
  liuyq@iccas.ac.cn(Y.Q.L.)
- Funds：
- DOI：10.1007/s10118-023-2952-0
  CLC：
- Received：22 December 2022，
  
  Revised：2023-1-29，
  
  Accepted：31 January 2023，
  
  Online First：03 March 2023，
  
  Published：01 May 2023
- Accepted：
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Li, Y. F.; Guo, Y. L.; Liu, Y. Q. Recent progress in donor-acceptor type conjugated polymers for organic field-effect transistors.Chinese J. Polym. Sci.2023,41, 652–670

Yi-Fan Li, Yun-Long Guo, Yun-Qi Liu. Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(5): 652-670.
Li, Y. F.; Guo, Y. L.; Liu, Y. Q. Recent progress in donor-acceptor type conjugated polymers for organic field-effect transistors.Chinese J. Polym. Sci.2023,41, 652–670 DOI： 10.1007/s10118-023-2952-0.

Yi-Fan Li, Yun-Long Guo, Yun-Qi Liu. Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors[J]. Chinese Journal of Polymer Science, 2023, 41(5): 652-670. DOI： 10.1007/s10118-023-2952-0.

摘要

We describe the recent progress in D-A conjugated polymers for OFETs from three aspects: (1) the modification of π-conjugated backbone

(2) the evolution of the polymerization methods and (3) the regulation of aggregate-state structure.

Abstract

The recent progress in the design and synthesis of high-performance donor-acceptor conjugated polymeric semiconducting materials is reviewed from the perspective of multiscale structures. The multiscale of conjugated polymers is from the primary one-dimensional polymer molecular scale to the secondary polymer-chains interaction scale

and then to the tertiary polymer aggregate scale. This review focuses on the design and synthesis of polymer molecules

proposes new classification rules

and rationally summarizes the design strategies and modulation methods of polymers. We describe the recent progress from these three aspects: (1) the modification of

-conjugated backbone

(2) the evolution of the polymerization methods

and (3) the regulation of aggregate-state structure.

关键词

Keywords

references

Zhao, Y.; Guo, Y.; Liu, Y . 25 th Anniversary article: recent advances in n-type and ambipolar organic field-effect transistors . Adv. Mater. , 2013 , 25 5372 - 5391 . DOI: 10.1002/adma.201302315 http://doi.org/10.1002/adma.201302315 .

Yang, Y.; Liu, Z.; Zhang, G.; Zhang, X.; Zhang, D . The effects of side chains on the charge mobilities and functionalities of semiconducting conjugated polymers beyond solubilities . Adv. Mater. , 2019 , 31 1903104 DOI: 10.1002/adma.201903104 http://doi.org/10.1002/adma.201903104 .

Russ, B.; Glaudell, A.; Urban, J. J.; Chabinyc, M. L.; Segalman, R. A . Organic thermoelectric materials for energy harvesting and temperature control . Nat. Rev. Mater. , 2016 , 1 16050 DOI: 10.1038/natrevmats.2016.50 http://doi.org/10.1038/natrevmats.2016.50 .

Yuvaraja, S.; Nawaz, A.; Liu, Q.; Dubal, D.; Surya, S. G.; Salama, K. N.; Sonar, P . Organic field-effect transistor-based flexible sensors . Chem. Soc. Rev. , 2020 , 49 3423 - 3460 . DOI: 10.1039/C9CS00811J http://doi.org/10.1039/C9CS00811J .

Brédas, J. L.; Li, Y.; Sun, H.; Zhong, C . Why can high charge-carrier mobilities be achieved along π -conjugated polymer chains with alternating donor-acceptor moieties . Adv. Theory Simul. , 2018 , 1 1800016 DOI: 10.1002/adts.201800016 http://doi.org/10.1002/adts.201800016 .

Lei, T.; Wang, J. Y.; Pei, J . Design, synthesis, and structure-property relationships of isoindigo-based conjugated polymers . Acc. Chem. Res. , 2014 , 47 1117 - 1126 . DOI: 10.1021/ar400254j http://doi.org/10.1021/ar400254j .

Li, J.; Zhao, Y.; Tan, H. S.; Guo, Y.; Di, C. A.; Yu, G.; Liu, Y.; Lin, M.; Lim, S. H.; Zhou, Y . A stable solution-processed polymer semiconductor with record high-mobility for printed transistors . Sci. Rep. , 2012 , 2 754 DOI: 10.1038/srep00754 http://doi.org/10.1038/srep00754 .

Yang, J.; Zhao, Z.; Wang, S.; Guo, Y.; Liu, Y . Insight into high-performance conjugated polymers for organic field-effect transistors . Chem , 2018 , 4 2748 - 2785 . DOI: 10.1016/j.chempr.2018.08.005 http://doi.org/10.1016/j.chempr.2018.08.005 .

Sun, H.; Guo, X.; Facchetti, A . High-performance n-type polymer semiconductors: applications, recent development, and challenges . Chem , 2020 , 6 1310 - 1326 . DOI: 10.1016/j.chempr.2020.05.012 http://doi.org/10.1016/j.chempr.2020.05.012 .

Guo, X.; Facchetti, A.; Marks, T. J . Imide- and amide-functionalized polymer semiconductors . Chem. Rev. , 2014 , 114 8943 - 9021 . DOI: 10.1021/cr500225d http://doi.org/10.1021/cr500225d .

Meager, I.; Nikolka, M.; Schroeder, B. C.; Nielsen, C. B.; Planells, M.; Bronstein, H.; Rumer, J. W.; James, D. I.; Ashraf, R. S.; Sadhanala, A . Thieno[3,2- b ]thiophene flanked isoindigo polymers for high performance ambipolar OFET applications . Adv. Funct. Mater. , 2014 , 24 7109 - 7115 . DOI: 10.1002/adfm.201402307 http://doi.org/10.1002/adfm.201402307 .

Song, E.; Ha, Y. H.; Kang, B.; Yun, H. J.; Kwon, S. K.; Kim, Y. H.; Cho, K . Effects of varying the lengths of the donor units in π -extended thienothiophene isoindigo-based polymer semiconductors . J. Mater. Chem. C , 2018 , 6 9972 - 9980 . DOI: 10.1039/C8TC02705F http://doi.org/10.1039/C8TC02705F .

Zhao, N.; Ai, N.; Cai, M.; Wang, X.; Wan, X.; Pei, J . Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors . Polym. Chem. , 2016 , 7 235 - 243 . DOI: 10.1039/C5PY01488C http://doi.org/10.1039/C5PY01488C .

Zhao, N.; Qiu, L.; Wang, X.; An, Z.; Wan, X . Synthesis of a thiophene-fused isoindigo derivative: a potential building block for organic semiconductors . Tetrahedr. Lett. , 2014 , 55 1040 - 1044 . DOI: 10.1016/j.tetlet.2013.12.076 http://doi.org/10.1016/j.tetlet.2013.12.076 .

Chen, B.; Yang, Y.; Cheng, P.; Chen, X.; Zhan, X.; Qin, J . Designing a thiophene-fused DPP unit to build an A-D-A molecule for solution-processed solar cells . J. Mater. Chem. A , 2015 , 3 6894 - 6900 . DOI: 10.1039/C5TA00294J http://doi.org/10.1039/C5TA00294J .

Zhuang, W.; Wang, S.; Tao, Q.; Ma, W.; Wang, E . Synthesis and electronic properties of diketopyrrolopyrrole-based polymers with and without ring-fusion . Macromolecules , 2021 , 54 970 - 980 . DOI: 10.1021/acs.macromol.0c02326 http://doi.org/10.1021/acs.macromol.0c02326 .

Jiang, W.; Liu, Z.; Zhu, D.; Zheng, W.; Chen, L.; Zhang, X.; Zhang, G.; Yi, Y.; Jiang, L.; Zhang, D . New synthetic approaches to N -aryl and π -expanded diketopyrrolopyrroles as new building blocks for organic optoelectronic materials . Angew. Chem. Int. Ed. , 2021 , 60 10700 - 10708 . DOI: 10.1002/anie.202102131 http://doi.org/10.1002/anie.202102131 .

Ni, Z.; Dong, H.; Wang, H.; Ding, S.; Zou, Y.; Zhao, Q.; Zhen, Y.; Liu, F.; Jiang, L.; Hu, W . Quinoline-flanked diketopyrrolopyrrole copolymers breaking through electron mobility over 6 cm 2 V –1 s –1 in flexible thin film devices . Adv. Mater. , 2018 , 30 1704843 DOI: 10.1002/adma.201704843 http://doi.org/10.1002/adma.201704843 .

Chen, H.; Wadsworth, A.; Ma, C.; Nanni, A.; Zhang, W.; Nikolka, M.; Luci, A. M. T.; Perdigao, L. M. A.; Thorley, K. J.; Cendra, C.; Larson, B.; Rumbles, G.; Anthopoulos, T. D.; Salleo, A.; Costantini, G.; Sirringhaus, H.; McCulloch, I . The effect of ring expansion in thienobenzo[ b ]indacenodithiophene polymers for organic field-effect transistors . J. Am. Chem. Soc. , 2019 , 141 18806 - 18813 . DOI: 10.1021/jacs.9b09367 http://doi.org/10.1021/jacs.9b09367 .

Fu, X.; Zhen, Y.; Ni, Z.; Li, Y.; Dong, H.; Siegel, J. S.; Hu, W . One-pot domino carbonylation protocol for aromatic diimides toward n-type organic semiconductors . Angew. Chem. Int. Ed. , 2020 , 59 14024 DOI: 10.1002/anie.202003179 http://doi.org/10.1002/anie.202003179 .

Hwang, H.; Khim, D.; Yun, J. M.; Jung, E.; Jang, S. Y.; Jang, Y. H.; Noh, Y. Y.; Kim, D. Y . Quinoidal molecules as a new class of ambipolar semiconductor originating from amphoteric redox behavior . Adv. Funct. Mater. , 2015 , 25 1146 - 1156 . DOI: 10.1002/adfm.201402758 http://doi.org/10.1002/adfm.201402758 .

Deng, Y.; Sun, B.; He, Y.; Quinn, J.; Guo, C.; Li, Y . Thiophene- S , S -dioxidized indophenine: a quinoid-type building block with high electron affinity for constructing n-type polymer semiconductors with narrow band gaps . Angew. Chem. Int. Ed. , 2016 , 55 3459 - 3462 . DOI: 10.1002/anie.201508781 http://doi.org/10.1002/anie.201508781 .

Tormos, G. V.; Belmore, K. A.; Cava, M. P . The indophenine reaction revisited. Properties of a soluble dialkyl derivative . J. Am. Chem. Soc. , 1993 , 115 11512 - 11515 . DOI: 10.1021/ja00077a057 http://doi.org/10.1021/ja00077a057 .

Huang, J.; Lu, S.; Chen, P.-A.; Wang, K.; Hu, Y.; Liang, Y.; Wang, M.; Reichmanis, E . Rational design of a narrow-bandgap conjugated polymer using the quinoidal thieno[3,2- b ]thiophene-based building block for organic field-effect transistor applications . Macromolecules , 2019 , 52 4749 - 4756 . DOI: 10.1021/acs.macromol.9b00370 http://doi.org/10.1021/acs.macromol.9b00370 .

Deng, Y.; Sun, B.; Quinn, J.; He, Y.; Ellard, J.; Guo, C.; Li, Y . Thiophene- S,S -dioxidized indophenines as high performance n-type organic semiconductors for thin film transistors . RSC Adv. , 2016 , 6 45410 - 45418 . DOI: 10.1039/C6RA06316K http://doi.org/10.1039/C6RA06316K .

Song, H.; Deng, Y.; Gao, Y.; Jiang, Y.; Tian, H.; Yan, D.; Geng, Y.; Wang, F . Donor-acceptor conjugated polymers based on indacenodithiophene derivative bridged diketopyrrolopyrroles: synthesis and semiconducting properties . Macromolecules , 2017 , 50 2344 - 2353 . DOI: 10.1021/acs.macromol.6b02781 http://doi.org/10.1021/acs.macromol.6b02781 .

Gao, R.; Wu, B.; Liang, Z.; Zhao, X.; Deng, Y.; Tian, H.; Geng, Y . Electronic properties modulation of tetraoxidothieno [3,2- b ] thiophene-based quinoidal compounds by terminal fluorination . Mater. Chem. Front. , 2020 , 4 891 - 898 . DOI: 10.1039/C9QM00690G http://doi.org/10.1039/C9QM00690G .

Ren, L.; Fan, H.; Huang, D.; Yuan, D.; Di, C; Zhu, X . Dithienoindophenines: p-type semiconductors designed by quinoid stabilization for solar-cell applications . Chem. Eur. J. , 2016 , 22 17136 - 17140 . DOI: 10.1002/chem.201603112 http://doi.org/10.1002/chem.201603112 .

Hwang, K.; Lee, M. H.; Kim, J.; Kim, Y.; Kim, Y.; Hwang, H.; Kim, I. B.; Kim, D. Y. . 3,4-Ethylenedioxythiophene-based isomer-free quinoidal building block and conjugated polymers for organic field-effect transistors . Macromolecules , 2020 , 53 1977 - 1987 . DOI: 10.1021/acs.macromol.9b02237 http://doi.org/10.1021/acs.macromol.9b02237 .

Turbiez, M.; Frère, P.; Allain, M.; Videlot, C.; Ackermann, J.; Roncali, J . Design of organic semiconductors: tuning the electronic properties of π -conjugated oligothiophenes with the 3,4-ethylenedioxythiophene (EDOT) building block . Chem. Eur. J. , 2005 , 11 3742 - 3752 . DOI: 10.1002/chem.200401058 http://doi.org/10.1002/chem.200401058 .

Sun, Y.; Zhang, Y.; Ran, Y.; Shi, L.; Zhang, Q.; Chen, J.; Li, Q.; Guo, Y.; Liu, Y . Methoxylation of quinoidal bithiophene as a single regioisomer building block for narrow-bandgap conjugated polymers and high-performance organic field-effect transistors . J. Mater. Chem. C , 2020 , 8 15168 - 15174 . DOI: 10.1039/D0TC02199G http://doi.org/10.1039/D0TC02199G .

Zhao, X.; Cai, H.; Deng, Y.; Jiang, Y.; Wang, Z.; Shi, Y.; Han, Y.; Geng, Y . Low-band gap conjugated polymers with strong absorption in the second near-infrared region based on diketopyrrolopyrrole-containing quinoidal units . Macromolecules , 2021 , 54 3498 - 3506 . DOI: 10.1021/acs.macromol.1c00124 http://doi.org/10.1021/acs.macromol.1c00124 .

Lu, S.; Drees, M.; Yao, Y.; Boudinet, D.; Yan, H.; Pan, H.; Wang, J.; Li, Y.; Usta, H.; Facchetti, A. . 3,6-Dithiophen-2-yl-diketopyrrolo[3,2- b ]pyrrole (isoDPPT) as an acceptor building block for organic opto-electronics . Macromolecules , 2013 . 3906 46 ( 3895 ): DOI: 10.1021/ma400568b http://doi.org/10.1021/ma400568b .

Li, B.; Zou, X.; Xiong, M.; Li, Q.; Kang, X.; Mu, Y.; Wang, J.; Pei, J.; Yang, C.; Lan, Z.; Wan, X . Thiazoloisoindigo-based ambipolar polymers for excellent balanced hole and electron mobility . Mater. Chem. Front. , 2022 , 6 3369 - 3381 . DOI: 10.1039/D2QM00612J http://doi.org/10.1039/D2QM00612J .

Zhang, W.; Mao, Z.; Chen, Z.; Huang, J.; Wei, C.; Gao, D.; Lin, Z.; Li, H.; Wang, L.; Yu, G . Ambipolar tetrafluorodiphenylethene-based donor-acceptor copolymers: synthesis, properties, backbone conformation and fluorine-induced conformational locks . Polym. Chem. , 2017 , 8 879 - 889 . DOI: 10.1039/C6PY01922F http://doi.org/10.1039/C6PY01922F .

Yu, S.; Peng, A.; Zhang, S.; Huang, H . Noncovalent conformational locks in organic semiconductors . Sci. China Chem. , 2018 , 61 1359 - 1367 . DOI: 10.1007/s11426-018-9315-2 http://doi.org/10.1007/s11426-018-9315-2 .

Yang, L.; Gu, W.; Yang, Y.; Hong, L.; Zhang, X.; Xiao, Y.; Wu, X.; Peng, A.; Huang, H . A highly planar nonfullerene acceptor with multiple noncovalent conformational locks for efficient organic solar cells . Small Methods , 2018 , 2 1700330 DOI: 10.1002/smtd.201700330 http://doi.org/10.1002/smtd.201700330 .

Huang, H.; Yang, L.; Facchetti, A.; Marks, T. J . Organic and polymeric semiconductors enhanced by noncovalent conformational locks . Chem. Rev. , 2017 , 117 10291 - 10318 . DOI: 10.1021/acs.chemrev.7b00084 http://doi.org/10.1021/acs.chemrev.7b00084 .

. 25th Anniversary article: progress in chemistry and applications of functional indigos fororganic electronics. . Adv. Mater. , 2013 , 25 6783 - 6800 . DOI: 10.1002/adma.201302652 http://doi.org/10.1002/adma.201302652 .

Kolaczkowski, M. A.; Liu, Y . Functional organic semiconductors based on bay-annulated indigo (BAI) . Chem. Rec. , 2019 , 19 1062 - 1077 . DOI: 10.1002/tcr.201800159 http://doi.org/10.1002/tcr.201800159 .

Seixas de Melo, J.; Rondão, R.; Burrows, H.; Melo, M.; Navaratnam, S.; Edge, R.; Voss, G . Photophysics of an indigo derivative (keto and leuco structures) with singular properties . J. Phys. Chem. A , 2006 , 110 13653 - 13661 . DOI: 10.1021/jp057451w http://doi.org/10.1021/jp057451w .

He, B.; Pun, A. B.; Zherebetskyy, D.; Liu, Y.; Liu, F.; Klivansky, L. M.; McGough, A. M.; Zhang, B. A.; Lo, K.; Russell, T. P . New form of an old natural dye: bay-annulated indigo (BAI) as an excellent electron accepting unit for high performance organic semiconductors . J. Am. Chem. Soc. , 2014 , 136 15093 - 15101 . DOI: 10.1021/ja508807m http://doi.org/10.1021/ja508807m .

Kolaczkowski, M. A.; He, B.; Liu, Y . Stepwise bay annulation of indigo for the synthesis of desymmetrized electron acceptors and donor-acceptor constructs . Org. lett. , 2016 , 18 5224 - 5227 . DOI: 10.1021/acs.orglett.6b02504 http://doi.org/10.1021/acs.orglett.6b02504 .

Yang, J.; Jiang, Y.; Tu, Z.; Zhao, Z.; Chen, J.; Yi, Z.; Li, Y.; Wang, S.; Yi, Y.; Guo, Y.; Liu, Y . High-performance ambipolar polymers based on electron-withdrawing group substituted bay-annulated indigo . Adv. Funct. Mater. , 2019 , 29 1804839 DOI: 10.1002/adfm.201804839 http://doi.org/10.1002/adfm.201804839 .

Yang, J.; Yang, X.; Chen, J.; Zhao, Z.; Jiang, Y.; Zhu, M.; Li, J.; Chi, K.; Wang, S.; Guo, Y.; Liu, Y . A multihalogenation strategy for ambipolar transistors and high-gain inverters with good noise margin . Sci. Bull. , 2022 , 67 1849 - 1853 . DOI: 10.1016/j.scib.2022.08.032 http://doi.org/10.1016/j.scib.2022.08.032 .

Fallon, K. J.; Wijeyasinghe, N.; Yaacobi-Gross, N.; Ashraf, R. S.; Freeman, D. M.; Palgrave, R. G.; Al-Hashimi, M.; Marks, T. J.; McCulloch, I.; Anthopoulos, T. D . A nature-inspired conjugated polymer for high performance transistors and solar cells . Macromolecules , 2015 , 48 5148 - 5154 . DOI: 10.1021/acs.macromol.5b00542 http://doi.org/10.1021/acs.macromol.5b00542 .

Fallon, K. J.; Wijeyasinghe, N.; Manley, E. F.; Dimitrov, S. D.; Yousaf, S. A.; Ashraf, R. S.; Duffy, W.; Guilbert, A. A.; Freeman, D. M.; Al-Hashimi, M . Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: molecular origin of ultrahigh n-type mobility . Chem. Mater. , 2016 , 28 8366 - 8378 . DOI: 10.1021/acs.chemmater.6b03671 http://doi.org/10.1021/acs.chemmater.6b03671 .

Park, H.; Kim, Y.; Kim, D.; Lee, S.; Kim, F. S.; Kim, B. J . Disintegrable n-type electroactive terpolymers for high-performance, transient organic electronics . Adv. Funct. Mater. , 2022 , 32 2106977 DOI: 10.1002/adfm.202106977 http://doi.org/10.1002/adfm.202106977 .

Tran, H.; Nikzad, S.; Chiong, J. A.; Schuster, N. J.; Peña-Alcántara, A. E.; Feig, V. R.; Zheng, Y. Q.; Bao, Z . Modular synthesis of fully degradable imine-based semiconducting p-type and n-type polymers . Chem. Mater. , 2021 , 33 7465 - 7474 . DOI: 10.1021/acs.chemmater.1c02258 http://doi.org/10.1021/acs.chemmater.1c02258 .

Liao, X.; Zhang, Z.; Liao, Q.; Liang, Q.; Ou, Y.; Xu, M.; Li, M.; Zhang, G.; Zhang, Y . Flexible and printable paper-based strain sensors for wearable and large-area green electronics . Nanoscale , 2016 , 8 13025 - 13032 . DOI: 10.1039/C6NR02172G http://doi.org/10.1039/C6NR02172G .

Lei, T.; Guan, M.; Liu, J.; Lin, H. C.; Pfattner, R.; Shaw, L.; McGuire, A. F.; Huang, T. C.; Shao, L.; Cheng, K. T.; Tok, J. B.; Bao, Z . Biocompatible and totally disintegrable semiconducting polymer for ultrathin and ultralightweight transient electronics . Proc. Natl. Acad. Sci. U. S. A. , 2017 , 114 5107 - 5112 . DOI: 10.1073/pnas.1701478114 http://doi.org/10.1073/pnas.1701478114 .

Tran, H.; Feig, V. R.; Liu, K.; Wu, H. C.; Chen, R.; Xu, J.; Deisseroth, K.; Bao, Z . Stretchable and fully degradable semiconductors for transient electronics . ACS Cent. Sci. , 2019 , 5 1884 - 1891 . DOI: 10.1021/acscentsci.9b00850 http://doi.org/10.1021/acscentsci.9b00850 .

Lei, T.; Dou, J.; Ma, Z.; Yao, C.; Liu, C.; Wang, J.; Pei, J . Ambipolar polymer field-effect transistors based on fluorinated isoindigo: high performance and improved ambient stability . J. Am. Chem. Soc. , 2012 , 134 20025 - 20028 . DOI: 10.1021/ja310283f http://doi.org/10.1021/ja310283f .

Sun, B.; Hong, W.; Yan, Z.; Aziz, H.; Li, Y . Record high electron mobility of 6.3 cm 2 V −1 s −1 achieved for polymer semiconductors using a new building block . Adv. Mater. , 2014 , 26 2636 - 2642 . DOI: 10.1002/adma.201305981 http://doi.org/10.1002/adma.201305981 .

Chen, H.; Guo, Y.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H.; Liu, Y . Highly π -extended copolymers with diketopyrrolopyrrole moieties for high-performance field-effect transistors . Adv. Mater. , 2012 , 24 4618 - 4622 . DOI: 10.1002/adma.201201318 http://doi.org/10.1002/adma.201201318 .

Ma, B.; Shi, Q.; Ma, X.; Li, Y.; Chen, H.; Wen, K.; Zhao, R.; Zhang, F.; Lin, Y.; Wang, Z.; Huang, H . Defect-free alternating conjugated polymers enabled by room-temperature stille polymerization . Angew. Chem. Int. Ed. , 2022 , 61 e202115969 DOI: 10.1002/anie.202115969 http://doi.org/10.1002/anie.202115969 .

Ni, Z.; Wang, H.; Dong, H.; Dang, Y.; Zhao, Q.; Zhang, X.; Hu, W . Mesopolymer synthesis by ligand-modulated direct arylation polycondensation towards n-type and ambipolar conjugated systems . Nat. Chem. , 2019 , 11 271 - 277 . DOI: 10.1038/s41557-018-0200-y http://doi.org/10.1038/s41557-018-0200-y .

Zhang, G.; Dai, Y.; Liu, Y.; Liu, J.; Lu, H.; Qiu, L.; Cho, K. . Facile green synthesis of isoindigo-based conjugated polymers using aldol polycondensation . Polym. Chem. , 2017 , 8 3448 - 3456 . DOI: 10.1039/c7py00484b http://doi.org/10.1039/c7py00484b .

Wang, G. J. N.; Molina-Lopez, F.; Zhang, H.; Xu, J.; Wu, H. C.; Lopez, J.; Shaw, L.; Mun, J.; Zhang, Q.; Wang, S.; Ehrlich, A.; Bao, Z . Nonhalogenated solvent processable and printable high-performance polymer semiconductor enabled by isomeric nonconjugated flexible linkers . Macromolecules , 2018 , 51 4976 - 4985 . DOI: 10.1021/acs.macromol.8b00971 http://doi.org/10.1021/acs.macromol.8b00971 .

Wang, G. J. N.; Zheng, Y.; Zhang, S.; Kang, J.; Wu, H. C.; Gasperini, A.; Zhang, H.; Gu, X.; Bao, Z . Tuning the cross-linker crystallinity of a stretchable polymer semiconductor . Chem. Mater. , 2018 , 31 6465 - 6475 . DOI: 10.1021/acs.chemmater.8b04314 http://doi.org/10.1021/acs.chemmater.8b04314 .

Chen, Z.; Zhang, W.; Wei, C.; Zhou, Y.; Pan, Y.; Wei, X.; Huang, J.; Wang, L.; Yu, G . High-electron mobility tetrafluoroethylene-containing semiconducting polymers . Chem. Mater. , 2020 , 32 2330 - 2340 . DOI: 10.1021/acs.chemmater.9b04425 http://doi.org/10.1021/acs.chemmater.9b04425 .

Li, M.; An, C.; Marszalek, T.; Baumgarten, M.; Yan, H.; Müllen, K.; Pisula, W . Controlling the surface organization of conjugated donor-acceptor polymers by their aggregation in solution . Adv. Mater. , 2016 , 28 9430 - 9438 . DOI: 10.1002/adma.201602660 http://doi.org/10.1002/adma.201602660 .

Zheng, Y.; Yao, Z.; Lei, T.; Dou, J.; Yang, C.; Zou, L.; Meng, X.; Ma, W.; Wang, J.; Pei, J . Unraveling the solution-state supramolecular structures of donor-acceptor polymers and their influence on solid-state morphology and charge-transport properties . Adv. Mater. , 2017 , 29 1701072 DOI: 10.1002/adma.201701072 http://doi.org/10.1002/adma.201701072 .

Noriega, R.; Rivnay, J.; Vandewal, K.; Koch, F. P. V.; Stingelin, N.; Smith, P.; Toney, M. F.; Salleo, A . A general relationship between disorder, aggregation and charge transport in conjugated polymers . Nat. Mater. , 2013 , 12 1038 - 1044 . DOI: 10.1038/nmat3722 http://doi.org/10.1038/nmat3722 .

Li, M.; Balawi, A. H.; Leenaers, P. J.; Ning, L.; Heintges, G. H. L.; Marszalek, T.; Pisula, W.; Wienk, M. M.; Meskers, S. C. J.; Yi, Y.; Laquai, F.; Janssen, R. A. J . Impact of polymorphism on the optoelectronic properties of a low-bandgap semiconducting polymer . Nat. Commun. , 2019 , 10 2867 DOI: 10.1038/s41467-019-10519-z http://doi.org/10.1038/s41467-019-10519-z .

Yao, Z. F.; Wang, Z. Y.; Wu, H. T.; Lu, Y.; Li, Q. Y.; Zou, L.; Wang, J. Y.; Pei, J . Ordered solid-state microstructures of conjugated polymers arising from solution-state aggregation . Angew. Chem. Int. Ed. , 2020 , 59 17467 - 17471 . DOI: 10.1002/anie.202007589 http://doi.org/10.1002/anie.202007589 .

Wu, H. T.; Yao, Z. F.; Xu, Z.; Kong, H. K.; Wang, X. Y.; Li, Q. Y.; Wang, J. Y.; Pei, J . Controlling solution-state aggregation and solid-state microstructures of conjugated polymers by tuning backbone conformation . Macromol. Rapid Commun. , 2022 , 43 2200069 DOI: 10.1002/marc.202200069 http://doi.org/10.1002/marc.202200069 .

Ding, L.; Wang, Z. Y.; Yao, Z. F.; Liu, N. F.; Wang, X. Y.; Zhou, Y. Y.; Luo, L.; Shen, Z.; Wang, J. Y.; Pei, J . Controllable transformation between the kinetically and thermodynamically stable aggregates in a solution of conjugated polymers . Macromolecules , 2021 , 54 5815 - 5824 . DOI: 10.1021/acs.macromol.1c00391 http://doi.org/10.1021/acs.macromol.1c00391 .

Zheng, Y. Q.; Yao, Z. F.; Dou, J. H.; Wang, Y.; Ma, W.; Zou, L.; Nikzad, S.; Li, Q. Y.; Sun, Z. H.; Yu, Z. A.; Zhang, W. B.; Wang, J. Y.; Pei, J . Influence of solution-state aggregation on conjugated polymer crystallization in thin films and microwire crystals . Giant , 2021 , 7 100064 DOI: 10.1016/j.giant.2021.100064 http://doi.org/10.1016/j.giant.2021.100064 .

Wang, Z.; Gao, M.; He, C.; Shi, W.; Deng, Y.; Han, Y.; Ye, L.; Geng, Y . Unraveling the molar mass dependence of shearing-induced aggregation structure of a high-mobility polymer semiconductor . Adv. Mater. , 2022 , 34 2108255 DOI: 10.1002/adma.202108255 http://doi.org/10.1002/adma.202108255 .

Wang, Z.; Song, X.; Jiang, Y.; Zhang, J.; Yu, X.; Deng, Y.; Han, Y.; Hu, W.; Geng, Y . A simple structure conjugated polymer for high mobility organic thin film transistors processed from nonchlorinated solvent . Adv. Sci. , 2019 , 6 1902412 DOI: 10.1002/advs.201902412 http://doi.org/10.1002/advs.201902412 .

Xu, C.; Wang, Z.; Dong, W.; He, C.; Shi, Y.; Bai, J.; Zhang, C.; Gao, M.; Jiang, H.; Deng, Y.; Ye, L.; Han, Y.; Geng, Y . Aggregation behavior and electrical performance control of isoindigo-based conjugated polymers via carbosilane side chain engineering . Macromolecules , 2022 , 55 10385 - 10394 . DOI: 10.1021/acs.macromol.2c01770 http://doi.org/10.1021/acs.macromol.2c01770 .

Wang, Z. Y.; Di Virgilio, 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 . Correlating charge transport properties of conjugated polymers in solution aggregates and thin-film aggregates . Angew. Chem. Int. Ed. , 2021 , 60 20483 - 20488 . DOI: 10.1002/anie.202107395 http://doi.org/10.1002/anie.202107395 .

Lei, Y.; Deng, P.; Lin, M.; Zheng, X.; Zhu, F.; Ong, B. S . Enhancing crystalline structural orders of polymer semiconductors for efficient charge transport via polymer-matrix-mediated molecular self-assembly . Adv. Mater. , 2016 , 28 6687 - 6694 . DOI: 10.1002/adma.201600580 http://doi.org/10.1002/adma.201600580 .

Um, H. A.; Lee, D. H.; Heo, D. U.; Yang, D. S.; Shin, J.; Baik, H.; Cho, M. J.; Choi, D. H . High aspect ratio conjugated polymer nanowires for high performance field-effect transistors and phototransistors . ACS Nano , 2015 , 9 5264 - 5274 . DOI: 10.1021/acsnano.5b01982 http://doi.org/10.1021/acsnano.5b01982 .

Xiao, C.; Zhao, G.; Zhang, A.; Jiang, W.; Janssen, R. A. J.; Li, W.; Hu, W.; Wang, Z . High performance polymer nanowire field-effect transistors with distinct molecular orientations . Adv. Mater. , 2015 , 27 4963 - 4968 . DOI: 10.1002/adma.201502617 http://doi.org/10.1002/adma.201502617 .

Yao, Z. F.; Zheng, Y. Q.; Dou, J. H.; Lu, Y.; Ding, Y. F.; Ding, L.; Wang, J. Y.; Pei, J . Approaching crystal structure and high electron mobility in conjugated polymer crystals . Adv. Mater. , 2021 , 33 e2006794 DOI: 10.1002/adma.202006794 http://doi.org/10.1002/adma.202006794 .

Zhang, X.; Bronstein, H.; Kronemeijer, A. J.; Smith, J.; Kim, Y.; Kline, R. J.; Richter, L. J.; Anthopoulos, T. D.; Sirringhaus, H.; Song, K . Molecular origin of high field-effect mobility in an indacenodithiophene-benzothiadiazole copolymer . Nat. Commun. , 2013 , 4 2238 DOI: 10.1038/ncomms3238 http://doi.org/10.1038/ncomms3238 .

Zhang, W.; Smith, J.; Watkins, S. E.; Gysel, R.; McGehee, M.; Salleo, A.; Kirkpatrick, J.; Ashraf, S.; Anthopoulos, T.; Heeney, M.; McCulloch, I . Indacenodithiophene semiconducting polymers for high-performance, air-stable transistors . J. Am. Chem. Soc. , 2010 , 132 11437 - 11439 . DOI: 10.1021/ja1049324 http://doi.org/10.1021/ja1049324 .

Venkateshvaran, D.; Nikolka, M.; Sadhanala, A.; Lemaur, V.; Zelazny, M.; Kepa, M.; Hurhangee, M.; Kronemeijer, A. J.; Pecunia, V.; Nasrallah, I.; Romanov, I.; Broch, K.; McCulloch, I.; Emin, D.; Olivier, Y.; Cornil, J.; Beljonne, D.; Sirringhaus, H . Approaching disorder-free transport in high-mobility conjugated polymers . Nature , 2014 , 515 384 - 388 . DOI: 10.1038/nature13854 http://doi.org/10.1038/nature13854 .

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