共轭高分子的精准合成

马博维; 史钦钦; 黄辉

doi:10.11777/j.issn1000-3304.2022.22432

您当前的位置：

首页 >

文章列表页 >

共轭高分子的精准合成

专论 | 更新时间：2023-05-31

- 共轭高分子的精准合成
- Precision Synthesis of Conjugated Polymers
- 高分子学报 2023年54卷第6期页码：791-802
- 作者机构：
  
  中国科学院大学材料科学与光电技术学院北京 100049
- 作者简介：
  
  [ "史钦钦，女，1982年生. 2006年本科毕业于河北工业大学高分子材料与工程系，2011年在中国科学院化学研究所获得博士学位. 先后在美国佐治亚理工学院(2011~2013年)和美国埃默里大学(2013~2018年)从事博士后研究. 2019年至今任中国科学院大学副教授. 主要科研方向是光电功能共轭小分子和高分子的绿色精准合成及应用探索. 2022年获国家优秀青年科学基金资助. ，E-mail: shiqinqin@ucas.ac.cn" ]
  [ "黄辉，男，1978年生. 2000年本科毕业于北京师范大学，2003年硕士毕业于中国科学院化学研究所，2008年在美国达特茅斯学院获得博士学位. 2008~2010年在美国西北大学从事博士后研究；2010~2013年在美国康菲石油公司(菲利普斯66石油公司)全球研发中心担任研究科学家. 2013年至今任中国科学院大学教授. 主要科研方向是有机/高分子半导体材料的合成与应用研究. 2017年入选J. Mater. Chem. A的Emerging Investigator；2019年获国家杰出青年科学基金资助；先后获得中国科学院朱李月华优秀教师奖、中国科学院优秀导师奖、唐立新优秀学者奖、领雁金奖等. huihuang@ucas.ac.cn" ]
- 基金信息：
  
  国家自然科学基金(基金号 ┣52222309;52173187);21774130, 21905277,51925306┫
- DOI：10.11777/j.issn1000-3304.2022.22432
  中图分类号：
- 纸质出版日期：2023-06-20，
  
  网络出版日期：2023-02-17，
  
  收稿日期：2022-12-13，
  
  录用日期：2023-01-17
扫描看全文
马博维,史钦钦,黄辉.共轭高分子的精准合成[J].高分子学报,2023,54(06):791-802.

Ma Bo-wei,Shi Qin-qin,Huang Hui.Precision Synthesis of Conjugated Polymers[J].ACTA POLYMERICA SINICA,2023,54(06):791-802.
马博维,史钦钦,黄辉.共轭高分子的精准合成[J].高分子学报,2023,54(06):791-802. DOI： 10.11777/j.issn1000-3304.2022.22432.

Ma Bo-wei,Shi Qin-qin,Huang Hui.Precision Synthesis of Conjugated Polymers[J].ACTA POLYMERICA SINICA,2023,54(06):791-802. DOI： 10.11777/j.issn1000-3304.2022.22432.

摘要

共轭高分子由于带隙容易调控、柔性、可溶液加工等优异性能，在有机光电领域具有重要的应用前景. 然而，聚合物普遍存在批次重现性差、结构缺陷多等问题，限制了聚合物的应用及发展. 本文总结了聚合物的结构缺陷，通过回顾本课题组以及国内外同行近几年的前沿工作，详细分析了共轭高分子材料均聚结构缺陷产生的原因和机理，同时介绍了目前较为常用的表征结构缺陷的方法，以及此类缺陷对器件性能的影响. 另外，还分析了当前3种合成共轭高分子材料的经典方法：Stille、Suzuki和直接芳基化聚合反应，介绍了这些方法在聚合物精准合成方面的前瞻性方法学的最新成果，并对本领域的发展进行了展望.

Abstract

Semiconducting polymers

especially

-conjugated donor-acceptor (D-A) copolymers with defect-free alternating structures

are essential materials for plastic electronics and optoelectronics owing to their advantages of variable/tunable chemical structures

tunable bandgaps and optical absorptions

excellent charge transport mobility

mechanical flexibility

and solution processability for printing. However

the drawbacks including batch-to-batch reproducibility

structural defects

and

etc

. hindered the commercial application for polymers. Herein

we analyzed the causes of structural defects

especially homocoupling defects in terms of their mechanism of generation by illustrating the example of Stille couplings and the side reactions

the characterization methods

including matrix-assisted laser desorption/ionization (MALDI)

nuclear magnetic resonance (NMR)

gel permeation chromatography (GPC) as well as ultraviolet-visible (UV-Vis) spectra

and the impact of defects on device performance by investigating the pioneering studies of this field within 5 years. Afterwards

three significant types of polymerizations to achieve copolymers with minimized structural defects have been illustrated separately

including Stille polymerization

Suzuki polymerization and direct arylation polymerization (DArP). From the synthetic perspective

the methodologies for the precision synthesis of conjugated polymers are in high demands and will pave the road for the development of organic electronics.

关键词

共轭高分子精准合成均聚结构缺陷器件性能

Keywords

Conjugated polymersPrecision synthesisHomocoupling defectsDevice performance

references

Carsten B.; He F.; Son H. J.; Xu T.; Yu L. Stille polycondensation for synthesis of functional materials. Chem. Rev., 2011, 111(3), 1493-1528. doi:10.1021/cr100320whttp://dx.doi.org/10.1021/cr100320w

Heeger A. J. Semiconducting polymers: the third generation. Chem. Soc. Rev., 2010, 39(7), 2354-2371. doi:10.1039/b914956mhttp://dx.doi.org/10.1039/b914956m

Phan S.; Luscombe C. K. Recent advances in the green, sustainable synthesis of semiconducting polymers. Trends. Chem., 2019, 1(7), 670-681. doi:10.1016/j.trechm.2019.08.002http://dx.doi.org/10.1016/j.trechm.2019.08.002

Zhao X.; Zhan X. Electron transporting semiconducting polymers in organic electronics. Chem. Soc. Rev., 2011, 40(7), 3728. doi:10.1039/c0cs00194ehttp://dx.doi.org/10.1039/c0cs00194e

Tong Y.; Xiao Z.; Du X.; Zuo C.; Li Y.; Lv M.; Yuan Y.; Yi C.; Hao F.; Hua Y.; Lei T.; Lin Q.; Sun K.; Zhao D.; Duan C.; Shao X.; Li W.; Yip H.-L.; Xiao Z.; Zhang B.; Bian Q.; Cheng Y.; Liu S.; Cheng M.; Jin Z.; Yang S.; Ding L. Progress of the key materials for organic solar cells. Sci. China Chem., 2020, 63(6), 758-765. doi:10.1007/s11426-020-9726-0http://dx.doi.org/10.1007/s11426-020-9726-0

Yan C.; Barlow S.; Wang Z.; Yan H.; Jen A. K. Y.; Marder S. R.; Zhan X. Non-fullerene acceptors for organic solar cells. Nat. Rev. Mater., 2018, 3(3), 18003. doi:10.1038/natrevmats.2018.3http://dx.doi.org/10.1038/natrevmats.2018.3

Cheng P.; Li G.; Zhan X.; Yang Y. Next-generation organic photovoltaics based on non-fullerene acceptors. Nat. Photonics, 2018, 12(3), 131-142. doi:10.1038/s41566-018-0104-9http://dx.doi.org/10.1038/s41566-018-0104-9

Hou J.; Inganas O.; Friend R. H.; Gao F. Organic solar cells based on non-fullerene acceptors. Nat Mater, 2018, 17(2), 119-128. doi:10.1038/nmat5063http://dx.doi.org/10.1038/nmat5063

Yang J.; Zhao Z.; Wang S.; Guo Y.; Liu Y. Insight into high-performance conjugated polymers for organic field-effect transistors. Chem, 2018, 4(12), 2748-2785. doi:10.1016/j.chempr.2018.08.005http://dx.doi.org/10.1016/j.chempr.2018.08.005

Dong H.; Fu X.; Liu J.; Wang Z.; Hu W. Key points for high-mobility organic field-effect transistors. Adv. Mater., 2013, 25(43), 6158-6183. doi:10.1002/adma.201302514http://dx.doi.org/10.1002/adma.201302514

Paterson A. F.; Singh S.; Fallon K. J.; Hodsden T.; Han Y.; Schroeder B. C.; Bronstein H.; Heeney M.; McCulloch I.; Anthopoulos T. D. Recent progress in high-mobility organic transistors: a reality check. Adv. Mater., 2018, 30(36), 1801079. doi:10.1002/adma.201801079http://dx.doi.org/10.1002/adma.201801079

Salehi A.; Fu X.; Shin D. H.; So F. Recent advances in OLED optical design. Adv. Funct. Mater., 2019, 29(15), 1808803. doi:10.1002/adfm.201808803http://dx.doi.org/10.1002/adfm.201808803

Borges-González J.; Kousseff C. J.; Nielsen C. B. Organic semiconductors for biological sensing. J. Mater. Chem. C., 2019, 7(5), 1111-1130. doi:10.1039/c8tc05900dhttp://dx.doi.org/10.1039/c8tc05900d

Ma L.; Wang S.; Li Y.; Shi Q.; Xie W.; Chen H.; Wang X.; Zhu W.; Jiang L.; Chen R. Air stable chalcogen-doped rubicenes with diradical character. CCS Chem., 2022, 1-8. doi:10.31635/ccschem.022.202201954http://dx.doi.org/10.31635/ccschem.022.202201954

Johansson Seechurn C. C.; Kitching M. O.; Colacot T. J.; Snieckus V. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 nobel prize. Angew. Chem. Int. Ed., 2012, 51(21), 5062-5085. doi:10.1002/anie.201107017http://dx.doi.org/10.1002/anie.201107017

Li H.; Seechurn C. C. C. J.; Colacot T. J. Development of preformed Pd catalysts for cross-coupling reactions, beyond the 2010 Nobel prize. ACS Catal., 2012, 2(6), 1147-1164. doi:10.1021/cs300082fhttp://dx.doi.org/10.1021/cs300082f

Cordovilla C.; Bartolomé C.; Martínez-Ilarduya J. M.; Espinet P. The Stille reaction, 38 years later. ACS Catal., 2015, 5(5), 3040-3053. doi:10.1021/acscatal.5b00448http://dx.doi.org/10.1021/acscatal.5b00448

Suzuki A. Cross-coupling reactions of organoboranes: an easy way to construct C―C bonds. Angew. Chem. Int. Ed., 2011, 50(30), 6722-6737. doi:10.1002/anie.201101379http://dx.doi.org/10.1002/anie.201101379

Cheng S.; Zhao R.; Seferos D. S. Precision synthesis of conjugated polymers using the Kumada methodology. Acc. Chem. Res., 2021, 54(22), 4203-4214. doi:10.1021/acs.accounts.1c00556http://dx.doi.org/10.1021/acs.accounts.1c00556

Gobalasingham N. S.; Thompson B. C. Direct arylation polymerization: a guide to optimal conditions for effective conjugated polymers. Prog. Polym. Sci., 2018, 83, 135-201. doi:10.1016/j.progpolymsci.2018.06.002http://dx.doi.org/10.1016/j.progpolymsci.2018.06.002

Lombeck F.; Komber H.; Gorelsky S. I.; Sommer M. Identifying homocouplings as critical side reactions in direct arylation polycondensation. ACS Macro. Lett., 2014, 3(8), 819-823. doi:10.1021/mz5004147http://dx.doi.org/10.1021/mz5004147

Blaskovits J. T.; Johnson P. A.; Leclerc M. Mechanistic origin of β‍-defect formation in thiophene-based polymers prepared by direct (hetero)arylation. Macromolecules, 2018, 51(20), 8100-8113. doi:10.1021/acs.macromol.8b01142http://dx.doi.org/10.1021/acs.macromol.8b01142

Kaake L.; Dang X. D.; Leong W. L.; Zhang Y.; Heeger A.; Nguyen T. Q. Effects of impurities on operational mechanism of organic bulk heterojunction solar cells. Adv. Mater., 2013, 25(12), 1706-1712. doi:10.1002/adma.201203786http://dx.doi.org/10.1002/adma.201203786

Streiter M.; Beer D.; Meier F.; Göhler C.; Lienert C.; Lombeck F.; Sommer M.; Deibel C. Homocoupling defects in a conjugated polymer limit exciton diffusion. Adv. Funct. Mater., 2019, 29(46), 1903936. doi:10.1002/adfm.201903936http://dx.doi.org/10.1002/adfm.201903936

Heintges G. H. L.; Janssen R. A. J. On the homocoupling of trialkylstannyl monomers in the synthesis of diketopyrrolopyrrole polymers and its effect on the performance of polymer-fullerene photovoltaic cells. RSC Adv., 2019, 9(28), 15703-15714. doi:10.1039/c9ra02670chttp://dx.doi.org/10.1039/c9ra02670c

Ashraf R. S.; Kronemeijer A. J.; James D. I.; Sirringhaus H.; McCulloch I. A new thiophene substituted isoindigo based copolymer for high performance ambipolar transistors. Chem. Comm., 2012, 48(33), 3939-3941. doi:10.1039/c2cc30169ehttp://dx.doi.org/10.1039/c2cc30169e

Estrada L. A.; Deininger J. J.; Kamenov G. D.; Reynolds J. R. Direct (hetero)arylation polymerization: an effective route to 3,4-propylenedioxythiophene-based polymers with low residual metal content. ACS Macro Lett., 2013, 2(10), 869-873. doi:10.1021/mz4003886http://dx.doi.org/10.1021/mz4003886

McCullough R. D.; Lowe R. D. Enhanced electrical conductivity in regioselectively synthesized poly(3-alkylthiophenes). J. Chem. Soc., Chem. Comm., 1992, (1), 70-72. doi:10.1039/c39920000070http://dx.doi.org/10.1039/c39920000070

Hendriks K. H.; Li W.; Heintges G. H. L.; van Pruissen G. W. P.; Wienk M. M.; Janssen R. A. J. Homocoupling defects in diketopyrrolopyrrole-based copolymers and their effect on photovoltaic performance. J. Am. Chem. Soc., 2014, 136(31), 11128-11133. doi:10.1021/ja505574ahttp://dx.doi.org/10.1021/ja505574a

Kuwabara J.; Fujie Y.; Maruyama K.; Yasuda T.; Kanbara T. Suppression of homocoupling side reactions in direct arylation polycondensation for producing high performance OPV materials. Macromolecules, 2016, 49(24), 9388-9395. doi:10.1021/acs.macromol.6b02380http://dx.doi.org/10.1021/acs.macromol.6b02380

Kuwabara J.; Tsuchida W.; Guo S.; Hu Z.; Yasuda T.; Kanbara T. Synthesis of conjugated polymers via direct C―H/C―Cl coupling reactions using a Pd/Cu binary catalytic system. Polym. Chem., 2019, 10(18), 2298-2304. doi:10.1039/c9py00232dhttp://dx.doi.org/10.1039/c9py00232d

Saito H.; Kuwabara J.; Yasuda T.; Kanbara T. Synthesis of polyfluoro arylene-based poly(arylenevinylene)s via Pd-catalyzed dehydrogenative direct alkenylation. Macromol. Rapid Commun., 2018, 39(18), 1800414. doi:10.1002/marc.201800414http://dx.doi.org/10.1002/marc.201800414

Wang Q.; Lenjani S. V.; Dolynchuk O.; Scaccabarozzi A. D.; Komber H.; Guo Y.; Günther F.; Gemming S.; Magerle R.; Caironi M.; Sommer M. Electron mobility of diketopyrrolopyrrole copolymers is robust against homocoupling defects. Chem. Mater., 2021, 33(2), 668-677. doi:10.1021/acs.chemmater.0c03998http://dx.doi.org/10.1021/acs.chemmater.0c03998

Espinet P.; Echavarren A. M. The mechanisms of the stille reaction. Angew. Chem. Int. Ed., 2004, 43(36), 4704-4734.

Rudenko A. E.; Thompson B. C. Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure. J. Polym. Sci., Part A-1: Polym. Chem., 2015, 53(2), 135-147. doi:10.1002/pola.27279http://dx.doi.org/10.1002/pola.27279

Adamo C.; Amatore C.; Ciofini I.; Jutand A.; Lakmini H. Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: key involvement of a palladium peroxo complex. J. Am. Chem. Soc., 2006, 128(21), 6829-6836. doi:10.1021/ja0569959http://dx.doi.org/10.1021/ja0569959

Lakmini H.; Ciofini I.; Jutand A.; Amatore C.; Adamo C. Pd-catalyzed homocoupling reaction of arylboronic acid: insights from density functional theory. J. Phys. Chem. A, 2008, 112(50), 12896-12903. doi:10.1021/jp801948uhttp://dx.doi.org/10.1021/jp801948u

Sakamoto J.; Rehahn M.; Wegner G.; Schlüter A. D. Suzuki polycondensation: polyarylenes à la carte. Macromol. Rapid Commun., 2009, 30(9-10), 653-687. doi:10.1002/marc.200900063http://dx.doi.org/10.1002/marc.200900063

Vangerven T.; Verstappen P.; Drijkoningen J.; Dierckx W.; Himmelberger S.; Salleo A.; Vanderzande D.; Maes W.; Manca J. V. Molar mass versus polymer solar cell performance: highlighting the role of homocouplings. Chem. Mater., 2015, 27(10), 3726-3732. doi:10.1021/acs.chemmater.5b00939http://dx.doi.org/10.1021/acs.chemmater.5b00939

Hong W.; Chen S.; Sun B.; Arnould M. A.; Meng Y.; Li Y. Is a polymer semiconductor having a "perfect" regular structure desirable for organic thin film transistors? Chem. Sci., 2015, 6(5), 3225-3235. doi:10.1039/c5sc00843chttp://dx.doi.org/10.1039/c5sc00843c

Lombeck F.; Komber H.; Fazzi D.; Nava D.; Kuhlmann J.; Stegerer D.; Strassel K.; Brandt J.; de Zerio Mendaza A. D.; Müller C. On the effect of prevalent carbazole homocoupling defects on the photovoltaic performance of PCDTBT:PC71BM solar cells. Adv. Energy Mater., 2016, 6(21), 1601232. doi:10.1002/aenm.201601232http://dx.doi.org/10.1002/aenm.201601232

Ma B.; Shi Q.; Ma X.; Li Y.; Chen H.; Wen K.; Zhao R.; Zhang F.; Lin Y.; Wang Z. Defect‐free alternating conjugated polymers enabled by room‐temperature Stille polymerization. Angew. Chem. Int. Ed., 2022, 61(16), e202115969. doi:10.1002/anie.202115969http://dx.doi.org/10.1002/anie.202115969

Mikhnenko O. V.; Kuik M.; Lin J.; van der Kaap N.; Nguyen T. Q.; Blom P. W. Trap-limited exciton diffusion in organic semiconductors. Adv. Mater., 2014, 26(12), 1912-1917. doi:10.1002/adma.201304162http://dx.doi.org/10.1002/adma.201304162

Lin J. D. A.; Mikhnenko O. V.; Chen J.; Masri Z.; Ruseckas A.; Mikhailovsky A.; Raab R. P.; Liu J.; Blom P. W. M.; Loi M. A.; García-Cervera C. J.; Samuel I. D. W.; Nguyen T. Q. Systematic study of exciton diffusion length in organic semiconductors by six experimental methods. Mater. Horiz., 2014, 1(2), 280-285. doi:10.1039/c3mh00089chttp://dx.doi.org/10.1039/c3mh00089c

Ward A. J.; Ruseckas A.; Samuel I. D. W. A shift from diffusion assisted to energy transfer controlled fluorescence quenching in polymer-fullerene photovoltaic blends. J. Phys. Chem. C, 2012, 116(45), 23931-23937. doi:10.1021/jp307538yhttp://dx.doi.org/10.1021/jp307538y

Rörich I.; Mikhnenko O. V.; Gehrig D.; Blom P. W. M.; Crăciun N. I. Influence of energetic disorder on exciton lifetime and photoluminescence efficiency in conjugated polymers. J. Phys. Chem. B, 2017, 121(6), 1405-1412. doi:10.1021/acs.jpcb.6b11813http://dx.doi.org/10.1021/acs.jpcb.6b11813

Tamai Y.; Ohkita H.; Benten H.; Ito S. Exciton diffusion in conjugated polymers: from fundamental understanding to improvement in photovoltaic conversion efficiency. J. Phys. Chem. Lett., 2015, 6(17), 3417-3428. doi:10.1021/acs.jpclett.5b01147http://dx.doi.org/10.1021/acs.jpclett.5b01147

Zarrabi N.; Yazmaciyan A.; Meredith P.; Kassal I.; Armin A. Anomalous exciton quenching in organic semiconductors in the low-yield limit. J. Phys. Chem. Lett., 2018, 9(20), 6144-6148. doi:10.1021/acs.jpclett.8b02484http://dx.doi.org/10.1021/acs.jpclett.8b02484

Li Z.; Shi Q.; Ma X.; Li Y.; Wen K.; Qin L.; Chen H.; Huang W.; Zhang F.; Lin Y. Efficient room temperature catalytic synthesis of alternating conjugated copolymers via C―S bond activation. Nat. Commun., 2022, 13(1), 1-8. doi:10.1038/s41467-021-27832-1http://dx.doi.org/10.1038/s41467-021-27832-1

Rooney J. J. Eyring transition-state theory and kinetics in catalysis. J. Mol. Catal. A: Chem., 1995, 96(1), L1-L3. doi:10.1016/1381-1169(94)00054-9http://dx.doi.org/10.1016/1381-1169(94)00054-9

Bao Z. N.; Chan W. K.; Yu L. P. Exploration of the Stille coupling reaction for the syntheses of functional polymers. J. Am. Chem. Soc., 1995, 117(50), 12426-12435. doi:10.1021/ja00155a007http://dx.doi.org/10.1021/ja00155a007

Lee S. M.; Park K. H.; Jung S.; Park H.; Yang C. Stepwise heating in stille polycondensation toward no batch-to-batch variations in polymer solar cell performance. Nat. Commun., 2018, 9(1), 1-8. doi:10.1038/s41467-018-03718-7http://dx.doi.org/10.1038/s41467-018-03718-7

Khan F.; Dlugosch M.; Liu X.; Banwell M. G. The palladium-catalyzed ullmann cross-coupling reaction: a modern variant on a time-honored process. Acc. Chem. Res., 2018, 51(8), 1784-1795. doi:10.1021/acs.accounts.8b00169http://dx.doi.org/10.1021/acs.accounts.8b00169

Farina V. New perspectives in the cross-coupling reactions of organostannanes. Pure Appl. Chem., 1996, 68(1), 73-78. doi:10.1351/pac199668010073http://dx.doi.org/10.1351/pac199668010073

Zhu T.; Jiang L.; Li Y.; Xie Z.; Li Z.; Lv L.; Chen H.; Zhao Z.; Jiang L.; Tang B. Converting thioether waste into organic semiconductors by carbon-sulfur bond activation. Angew. Chem. Int. Ed., 2019, 58(15), 5044-5048. doi:10.1002/anie.201901274http://dx.doi.org/10.1002/anie.201901274

Jiang X. F.; Huang H.; Chai Y. F.; Lohr T. L.; Yu S. Y.; Lai W.; Pan Y. J.; Delferro M.; Marks T. J. Hydrolytic cleavage of both CS2 carbon-sulfur bonds by multinuclear Pd(II) complexes at room temperature. Nat. Chem., 2017, 9(2), 188-193. doi:10.1038/nchem.2637http://dx.doi.org/10.1038/nchem.2637

Lennox A. J. J.; Lloyd-Jones G. C. Selection of boron reagents for Suzuki-Miyaura coupling. Chem. Soc. Rev., 2014, 43(1), 412-443. doi:10.1039/c3cs60197hhttp://dx.doi.org/10.1039/c3cs60197h

Knapp D. M.; Gillis E. P.; Burke M. D. A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates. J. Am. Chem. Soc., 2009, 131(20), 6961-6963. doi:10.1021/ja901416phttp://dx.doi.org/10.1021/ja901416p

Wong M. S.; Zhang X. L. Ligand promoted palladium-catalyzed homo-coupling of arylboronic acids. Tetrahedron Lett., 2001, 42(24), 4087-4089. doi:10.1016/s0040-4039(01)00637-2http://dx.doi.org/10.1016/s0040-4039(01)00637-2

Bura T.; Beaupré S.; Légaré M. A.; Quinn J.; Rochette E.; Blaskovits J. T.; Fontaine F. G.; Pron A.; Li Y.; Leclerc M. Direct heteroarylation polymerization: guidelines for defect-free conjugated polymers. Chem. Sci., 2017, 8(5), 3913-3925. doi:10.1039/c7sc00589jhttp://dx.doi.org/10.1039/c7sc00589j

Sui Y.; Shi Y.; Deng Y.; Li R.; Bai J.; Wang Z.; Dang Y.; Han Y.; Kirby N.; Ye L.; Geng Y. Direct arylation polycondensation of chlorinated thiophene derivatives to high-mobility conjugated polymers. Macromolecules, 2020, 53(22), 10147-10154. doi:10.1021/acs.macromol.0c02206http://dx.doi.org/10.1021/acs.macromol.0c02206

Guo K.; Bai J.; Jiang Y.; Wang Z.; Sui Y.; Deng Y.; Han Y.; Tian H.; Geng Y. Diketopyrrolopyrrole‐based conjugated polymers synthesized via direct arylation polycondensation for high mobility pure n‐channel organic field‐effect transistors. Adv. Funct. Mater., 2018, 28(31), 1801097. doi:10.1002/adfm.201801097http://dx.doi.org/10.1002/adfm.201801097

Leclerc M.; Brassard S.; Beaupré S. Direct (hetero) arylation polymerization: toward defect-free conjugated polymers. Polym. J., 2020, 52(1), 13-20. doi:10.1038/s41428-019-0245-9http://dx.doi.org/10.1038/s41428-019-0245-9

Dudnik A. S.; Aldrich T. J.; Eastham N. D.; Chang R. P.; Facchetti A.; Marks T. J. Tin-free direct C―H arylation polymerization for high photovoltaic efficiency conjugated copolymers. J. Am. Chem. Soc., 2016, 138(48), 15699-15709. doi:10.1021/jacs.6b10023http://dx.doi.org/10.1021/jacs.6b10023

Zhang J.; Parker T. C.; Chen W.; Williams L.; Khrustalev V. N.; Jucov E. V.; Barlow S.; Timofeeva T. V.; Marder S. R. C―H-activated direct arylation of strong benzothiadiazole and quinoxaline-based electron acceptors. J. Org. Chem., 2016, 81(2), 360-370. doi:10.1021/acs.joc.5b02551http://dx.doi.org/10.1021/acs.joc.5b02551

Shi Q.; Tatum W.; Zhang J.; Scott C.; Luscombe C. K.; Marder S. R.; Blakey S. B. The direct arylation polymerization (DArP) of well‐defined alternating copolymers based on 5,6‐dicyano[2,1,3]benzothiadiazole (DCBT). Asian. J. Org. Chem., 2018, 7(7), 1419-1425. doi:10.1002/ajoc.201800232http://dx.doi.org/10.1002/ajoc.201800232

Liu C.; Wang K.; Hu X.; Yang Y.; Hsu C. H.; Zhang W.; Xiao S.; Gong X.; Cao Y. Molecular weight effect on the efficiency of polymer solar cells. ACS Appl. Mater. Interfaces, 2013, 5(22), 12163-12167. doi:10.1021/am404157thttp://dx.doi.org/10.1021/am404157t

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(3), 271-277. doi:10.1038/s41557-018-0200-yhttp://dx.doi.org/10.1038/s41557-018-0200-y

Liu Y.; Xian K.; Zhang X.; Gao M.; Shi Y.; Zhou K.; Deng Y.; Hou J.; Geng Y.; Ye L. A mixed-ligand strategy to modulate P3HT regioregularity for high-efficiency solar cells. Macromolecules, 2022, 55(8), 3078-3086. doi:10.1021/acs.macromol.1c02404http://dx.doi.org/10.1021/acs.macromol.1c02404

Yang C.; Zhang S.; Ren J.; Gao M.; Bi P.; Ye L.; Hou J. Molecular design of a non-fullerene acceptor enables a P3HT-based organic solar cell with 9.46% efficiency. Energy Environ. Sci., 2020, 13(9), 2864-2869. doi:10.1039/d0ee01763ahttp://dx.doi.org/10.1039/d0ee01763a

Zhang X.; Shi Y.; Dang Y.; Liang Z.; Wang Z.; Deng Y.; Han Y.; Hu W.; Geng Y. Direct arylation polycondensation of β-fluorinated bithiophenes to polythiophenes: effect of side chains in C―Br monomers. Macromolecules, 2022, 55(18), 8095-8105. doi:10.1021/acs.macromol.2c01266http://dx.doi.org/10.1021/acs.macromol.2c01266

Iizuka E.; Wakioka M.; Ozawa F. Mixed-ligand approach to palladium-catalyzed direct arylation polymerization: Synthesis of donor-acceptor polymers with dithienosilole (DTS) and thienopyrroledione (TPD) units. Macromolecules, 2015, 48(9), 2989-2993. doi:10.1021/acs.macromol.5b00526http://dx.doi.org/10.1021/acs.macromol.5b00526

Iizuka E.; Wakioka M.; Ozawa F. Mixed-ligand approach to palladium-catalyzed direct arylation polymerization: Effective prevention of structural defects using diamines. Macromolecules, 2016, 49(9), 3310-3317. doi:10.1021/acs.macromol.6b00441http://dx.doi.org/10.1021/acs.macromol.6b00441

Wakioka M.; Morita H.; Ichihara N.; Saito M.; Osaka I.; Ozawa F. Mixed-ligand approach to palladium-catalyzed direct arylation polymerization: synthesis of donor-acceptor polymers containing unsubstituted bithiophene units. Macromolecules, 2019, 53(1), 158-164. doi:10.1021/acs.macromol.9b02298http://dx.doi.org/10.1021/acs.macromol.9b02298

更多指标>

浏览量

132

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

高分子光催化材料表面活性位点及其反应机理探究

光电高分子材料的研究进展