Design, Synthesis, and Properties of Conjuated Molecules with Isatin-Fused Acenaphthenequinone Imide Moieties

doi:10.6023/cjoc202005035

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2919-2928.DOI: 10.6023/cjoc202005035 Previous Articles Next Articles

靛红并苊醌二甲酰亚胺类共轭分子的设计合成及性质研究

谭丹^a, 吴赛^a, 魏欢^b, 胡袁源^b, 陈华杰^a

a 湘潭大学化学学院环境友好化学与应用教育部重点实验室湖南湘潭 411105;
b 湖南大学物理与微电子科学学院微纳光电器件及应用教育部重点实验室长沙 410082

收稿日期:2020-05-14 修回日期:2020-06-12 发布日期:2020-06-28
通讯作者: 陈华杰 E-mail:chenhjoe@163.com, chenhjoe@xtu.edu.cn
基金资助:
国家自然科学基金（No.21875202）、湖南省自然科学基金杰出青年基金（No.2018JJ1024）和湖南省科技厅计划（No.2017RS3048）资助项目.

Design, Synthesis, and Properties of Conjuated Molecules with Isatin-Fused Acenaphthenequinone Imide Moieties

Tan Dan^a, Wu Sai^a, Wei Huan^b, Hu Yuanyuan^b, Chen Huajie^a

a Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105;
b Key Laboratory for Micro/Nano Optoelectronic Devices of Ministry of Education, School of Physics and Electronics, Hunan University, Changsha 410082

Received:2020-05-14 Revised:2020-06-12 Published:2020-06-28
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21875202), the Hunan Provincial Natural Science Foundation of China (No. 2018JJ1024), and the Science and Technology Planning Project of Hunan Province (No. 2017RS3048).

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Abstract

Two highly electron-deficient, novel isoindigo (IID) derivative acceptor units, including isatin-fused acenaphthenequinone imide (A1) and nitrogen-doped isatin-fused acenaphthenequinone imide (A2), were designed and synthesized via Knoevenagel consendation reaction. In comparison with the well-known IID unit, both A1 and A2 acceptor units exhibit reduced LUMO energy levels (ca. -4.0 eV) and extended π-conjugation backbone owing to the incorporation of strongly electron-withdrawing acenaphthenequinone imide. The properties observed here for both A1 and A2 are thus indicative of promising potential in the development of n-type organic semiconductors. On the basis of both A1 and A2 acceptor units, two A-A type organic π-conjugated molecules (BA1 and BA2) were further designed and synthesized by self-coupling of two identical A1 or A2 acceptor units. The effect of pyridal nitrogen on the backbone structure, optical absorption, energy level, and carrier mobility of the as-prepared π-conjugated molecules is studied systematically. The comparative investigation reveals that self-coupling of dual acceptor units into BA1 and BA2 not only endows them with extended conjugation backbone and enhanced molecular symmetry, but also improves their light-capturing abilities in the whole ultraviolet-visible region as relative to their parent acceptor units (A1 and A2). Moreover, the pyridal N-containing BA1 and BA2 possess enhanced backbone coplanarity and electron affinity as compared to their parent units (A1 and A2), thereby leading to reduced HOMO and LUMO energy levels. Finally, n-type thin-film transistors are further fabricated by adopting both BA1 and BA2 as the active layers, affording the electron motilities of 1.64×10^-3 and 2.52×10^-3 cm²·V^-1·s^-1, respectively.

Key words: isatin, acenaphthenequinone imide, isoindigo, electron mobility

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Tan Dan, Wu Sai, Wei Huan, Hu Yuanyuan, Chen Huajie. Design, Synthesis, and Properties of Conjuated Molecules with Isatin-Fused Acenaphthenequinone Imide Moieties[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2919-2928.

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[1] Bharitkar, Y. P.; Datta, S.; Sett, S.; Marathee, N.; Khan, P.; Mondal, N. B. Chem. Biol. Interact. 2017, 7, 19.
[2] Mei, J.; Graham, K. R.; Stalder, R.; Reynolds, J. R. Org. Lett. 2010, 12, 660.
[3] Papageorgiou, C.; Borer, X. Helv. Chim. Acta 1988, 71, 1079.
[4] Ding, L.; Wang, Z. Y.; Wang, J. Y.; Pei, J. Chin. J. Chem. 2020, 38, 13.
[5] Lu, Y.; Ding, Y. F.; Wang, J. Y.; Pei, J. Chin. J. Org. Chem. 2016, 36, 2272(in Chinese). (卢阳, 丁一凡, 王婕妤, 裴坚, 有机化学, 2016, 36, 2272.)
[6] (a) Wang, E. G.; Mammo, W.; Andersson, M. R. Adv. Mater. 2014, 26, 1801.
(b) Chen, H. J. Chin. J. Org. Chem. 2016, 36, 460(in Chinese). (陈华杰, 有机化学, 2016, 36, 2272.)
[7] Estrada, L. A.; Liu, D. Y.; Salazar, D. H.; Dyer, A. L.; Reynolds, J. R. Macromolecules 2012, 45, 8211.
[8] Bogdanov, A.; Mironov, V.; Musin, L.; Musin, R. Synthesis 2010, 3268.
[9] El-Kateb, A.; Hennawy, I.; Shabana, R.; Osman, F. Phosphorus. Sulfur Relat. Elem. 1984, 20, 329.
[10] Zhang, G. B.; Fu, Y. Y.; Xie, Z. Y.; Zhang, Q. Macromolecules 2011, 44, 1414.
[11] Cao, Y. Y.; Dou, J. H.; Zhao, N. J.; Zhang, S. M.; Zheng, Y. Q.; Zhang, J. P.; Wang, J. Y.; Pei, J.; Wang, Y. P. Chem. Mater. 2017, 29, 718.
[12] Ashraf, R. S.; Kronemeijer, A. J.; James, D. I.; Sirringhaus, H.; McCulloch, I. Chem. Commun. 2012, 48, 3939.
[13] Li, C. C.; Un, H. I.; Pei, J. W.; Cai, M.; Wang, X.; Wang, J. Y.; Lan, Z. G.; Pei, J.; Wan, X. B. Chem. Eur. J. 2018, 24, 9807.
[14] Huang, J. Y.; Mao, Z. P.; Chen, Z. H.; Gao, D.; Wei, C. Y.; Zhang, W. F.; Yu, G. Chem. Mater. 2016, 28, 2209.
[15] Gao, Y.; Deng, Y. F.; Tian, H. K.; Zhang, J. D.; Yan, D. H.; Geng, Y. H.; Wang, F. S. Adv. Mater. 2017, 29, 1606217.
[16] Yang, J.; Zhao, Z. Y.; Geng, H.; Cheng, C. L.; Chen, J. Y.; Sun, Y. L.; Shi, L. X.; Yi, Y. P.; Shuai, Z. G.; Guo, Y. L.; Wang, S.; Liu, Y. Q. Adv. Mater. 2017, 29, 1702115.
[17] Lei, T.; Dou, J. H.; Ma, Z. J.; Liu, C. J.; Wang, J. Y.; Pei, J. Chem. Sci. 2013, 4, 2447.
[18] Hasegawa, T.; Ashizawa, M.; Matsumoto, H. RSC Adv. 2015, 5, 61035.
[19] Xu, S. L.; Ai, N.; Zhao, N.; Lan, Z. G.; Wang, X.; Pei, J.; Wan, X. B. RSC Adv. 2015, 5, 8340.
[20] Wan, Y.; Ashraf, R. S.; Nielsen, C. B.; Collado-Fregoso, E.; Niazi, M. R.; Yousaf, S. A.; Kirkus, M.; Chen, H. Y.; Amassian, A.; Durrant, J. R.; McCullon, I. Adv. Mater. 2015, 27, 4702.
[21] Jiang, Y.; Zheng, X. H.; Deng, Y. F.; Tian, H. K.; Ding, J. Q.; Xie, Z. G.; Geng, Y. H.; Wang, F. S. Angew. Chem., Int. Ed. 2018, 57, 10283.
[22] Lei, T.; Dou, J. H.; Cao, X. Y.; Wang, J. Y.; Pei, J. J. Am. Chem. Soc. 2013, 135, 12168.
[23] Ma, S. X.; Zhang, G. B.; Wang, F. F.; Dai, Y. R.; Lu, H. B.; Qiu, L. Z.; Ding, Y. S.; Cho, K. Macromolecules 2018, 51, 5704.
[24] He, Y.; Quinn, J.; Deng, Y.; Li, Y. Org. Electron. 2016, 35, 41.
[25] Jiang, Y.; Gao, Y.; Tian, H. K.; Ding, J. Q.; Yan, D. H; Geng, Y. H.; Wang, F. S. Macromolecules 2016, 49, 2135.
[26] Mei, J. G.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. N. J. Am. Chem. Soc. 2011, 133, 20130.
[27] Lei, T.; Dou, J. H.; Pei, J. Adv. Mater. 2012, 24, 6457.
[28] Mei, J. G.; Wu, H. C.; Diao, Y.; Appleton, A.; Wang, H.; Zhou, Y.; Lee, W. Y.; Kurosawa, T.; Chen, W. C.; Bao, Z. N. Adv. Funct. Mater. 2015, 25, 3455.
[29] Lei, T.; Wang, J. Y.; Pei, J. Acc. Chem. Res. 2014, 47, 1117.
[30] Lan, L. Y.; Chen, Z. M.; Ying, L.; Huang, F.; Cao, Y. Org. Electron. 2016, 30, 176.
[31] Li, X. L.; Guo, J.; Yang, L. F.; Chao, M. H.; Zheng, L. P; Ma, Z. Y.; Hu, Y. Y.; Zhao, Y.; Chen, H. J.; Liu, Y. Q. Front. Chem. 2019, 7, 362.
[32] Li, H. Y.; Kim, F. S.; Ren, G. Q.; Hollenbeck, E. C.; Subramaniyan, S.; Jenekhe, S. A. Angew. Chem., Int. Ed. 2013, 52, 5513.
[33] Li, H. Y.; Kim, S.; Ren, G. Q.; Jenekhe, S. A. J. Am. Chem. Soc. 2013, 135, 14920.
[34] Li, H. Y.; Earmme, T.; Ren, G. Q.; Saeki, A.; Yoshikawa, S.; Murari, N. M.; Subramaniyan, S.; Crane, M. J.; Seki, S.; Jenekhe, S. A. J. Am. Chem. Soc. 2014, 136, 14589.
[35] Hwang, Y. J.; Li, H. Y.; Courtright, B. A. E.; Subramaniyan, S.; Jenekhe, S. A. Adv. Mater. 2016, 28, 124.
[36] Kolhe, N. B.; West, S. M.; Tran, D. K.; Ding, X. M.; Kuzuhara, D.; Yoshimot, N.; Koganezawa, T.; Jenekhe, S. A. Chem. Mater. 2020, 32, 195.
[37] Qian, X.; Zhu, Y. Z.; Song, J.; Gao, X. P.; Zheng, J. Y. Org. Lett. 2013, 15, 6034.
[38] Zhao, D.; Hu, J. Y.; Liu, Z. J.; Xiao, B.; Wang, X. Z.; Zhou, E. J.; Zhang, Q. Dyes Pigm. 2018, 151, 102.
[39] Jiro, T.; Tong, Z. W.; Yasuji, I. ARKIVOC 2001, 67.
[40] Echegaray, P. D.; Mancheño, M. J.; Arrechea-Marcos, I.; Juárez, R.; López-Espejo, G.; Navarrete, J. T. L.; Ramos, M. M.; Seoane, C.; Ortiz, R. P.; Segura, J. L. J. Org. Chem. 2016, 81, 11256.
[41] Ding, L.; Yang, C. Y.; Su, Z. M.; Pei, J. Sci. China Chem. 2015, 58, 364.
[42] Chen, H. J.; Cai, G. S.; Guo, A. K.; Zhao, Z. Y.; Kuang, J. H.; Zheng, L. P.; Zhao, L. L.; Chen, J. Y.; Guo, Y. L.; Liu, Y. Q. Macromolecules 2019, 52, 6149.
[43] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H. Vreven, T.; Montgomery, J. A.; Jr., Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc, Wallingford CT, 2009.
[44] Cao, Q. F.; Xiong, W. T.; Chen, H. J.; Cai, G. S.; Wang, G.; Zheng, L. P.; Sun, Y. M. J. Mater. Chem. A 2017, 5, 7451.

靛红并苊醌二甲酰亚胺类共轭分子的设计合成及性质研究

Design, Synthesis, and Properties of Conjuated Molecules with Isatin-Fused Acenaphthenequinone Imide Moieties

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