Advances in Organofluorine Compounds with Aggregation-Induced Emission

doi:10.6023/cjoc202003051

Abstract

Aggregation-induced emission (AIE) compounds have attracted much attention due to their important potential applications in biological and chemical sensing, luminescent materials, display and other areas. As an important class of functional molecules, organofluorine compounds have been widely studied in areas such as organic chemitry and materials chemistry. The organofluorine compounds with AIE properties are summarized and classified. The currently reported AIE organofluorine compounds include the fluorinated tetraphenylethene (TPE) derivatives, 9,10-distyrylanthracene (DSA) derivatives, cyanostilbene derivatives, distyrylbenzene derivatives, fluorinated polymers, carborane clusters, room temperature phosphorescent molecules, and some other fluorinated structures. With fluorine atoms in the structures, the stability of the resulting AIE compounds is generally improved, and fluorine atoms often participate in the intermolecular interactions leading to significant changes in the structure of the aggregation state, and hence changes in luminescence properties, for example, emission enhancement, bathochromism or hypsochromism of the emissions, improvement of the emission quantum yield and lifetime. The prospects of the future study are also discussed.

Key words: aggregation-induced emission, organic luminescent material, organofluorine compound, stimuli responsiveness

Cite this article

Qin Chengyuan, Liu Wei, Nie Yong, Gao Ying, Miao Jinling, Li Tianrui, Jiang Xuchuan. Advances in Organofluorine Compounds with Aggregation-Induced Emission[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2232-2253.

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References

[1] Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan,X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, 1740.
[2] Mei, J.; Hong, Y.; Lam, J. W.; Qin, A.; Tang, Y.; Tang, B. Z. Adv. Mater. 2014, 26, 5429.
[3] Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
[4] Hong, Y.; Lam, J. W.; Tang, B. Z. Chem. Commun. 2009, 4332.
[5] Luo, J.; Song, K.; Gu, F. L.; Miao, Q. Chem. Sci. 2011, 2, 2029.
[6] Leung, N. L.; Xie, N.; Yuan, W.; Liu, Y.; Wu, Q.; Peng, Q.; Miao, Q.; Lam, J. W.; Tang, B. Z. Chem.-Eur. J. 2014, 20, 15349.
[7] Yao, L.; Zhang, S.; Wang, R.; Li, W.; Shen, F.; Yang, B.; Ma, Y. Angew. Chem., Int. Ed. 2014, 53, 2119.
[8] Liu, J.; Meng, Q.; Zhang, X.; Lu, X.; He, P.; Jiang, L.; Dong, H.; Hu, W. Chem. Commun. 2013, 49, 1199.
[9] Babudri, F.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003.
[10] Zhang, Q.; Kelly, M. A.; Bauer, N.; You, W. Acc. Chem. Res. 2017, 50, 2401.
[11] Farinola, G. M.; Babudri, F.; Cardone, A.; Hassan Omar, O.; Martinelli, C.; Naso, F.; Pinto, V.; Ragni, R. Adv. Sci. Technol. 2010, 75, 108.
[12] MilianMedina, B.; Gierschner, J. J. Phys. Chem. Lett. 2017, 8, 91.
[13] Chen, M.; Sun, J.; Qin, A.; Tang, B. Z. Chin. Sci. Bull. 2016, 61, 304(in Chinese). (陈明, 孙景志, 秦安军, 唐本忠, 科学通报, 2016, 61, 304.)
[14] Shen, P.; Zhuang, Z.; Zhao, Z.; Tang, B. Z. J. Mater. Chem. C 2018, 6, 11835.
[15] Guo, L. X.; Xing, Y.; Wang, M.; Sun, Y.; Zhang, X.; Lin, B. P.; Yang, H. J. Mater. Chem. C 2019, 7, 4828.
[16] Fang, G.; Liu, J.; Zhang, C.; Liu, B. ACS Appl. Mater. Interfaces 2018, 10, 11546.
[17] Wang, N.; Zhang, J.; Xu, X.; Feng, S. Dalton Trans. 2020, 49, 1883.
[18] Shimizu, S.; Murayama, A.; Haruyama, T.; Iino, T.; Mori, S.; Furuta, H.; Kobayashi, N. Chem.-Eur. J. 2015, 21, 12996.
[19] Wang, X.; Wu, Y.; Liu, Q.; Li, Z.; Yan, H.; Ji, C.; Duan, J.; Liu, Z. Chem. Commun. 2015, 51, 784.
[20] Yamaguchi, M.; Ito, S.; Hirose, A.; Tanaka, K.; Chujo, Y. Mater. Chem. Front. 2017, 1, 1573.
[21] Ravotto, L.; Ceroni, P. Coord. Chem. Rev. 2017, 346, 62.
[22] Alam, P.; Climent, C.; Alemany, P.; Laskar, I. J. Photochem. Photobiol., C 2019, 41, 100317.
[23] Dong, W.; Fei, T.; PalmaCando, A.; Scherf, U. Polym. Chem. 2014, 5, 4048.
[24] Zhang, J.; Yang, Q.; Zhu, Y.; Liu, H.; Chi, Z.; Su, C. Dalton Trans. 2014, 43, 15785.
[25] Obora, Y.; Moriya, H.; Tokunaga, M.; Tsuji, Y. Chem. Commun. 2003, 2820.
[26] Mills, N. S.; Tirla, C.; Benish, M. A.; Rakowitz, A. J.; Bebell, L. M.; Hurd, C. M. M.; Bria, A. L. M. J. Org. Chem. 2005, 70, 10709.
[27] Xue, F.; Zhao, J.; Hor, T. S. A.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 3189.
[28] Lin, Y.; Chen, G.; Zhao, L.; Yuan, W. Z.; Zhang, Y.; Tang, B. Z. J. Mater. Chem. C 2015, 3, 112.
[29] Yang, Z.; Qin, W.; Leung, N. L. C.; Arseneault, M.; Lam, J. W. Y.; Liang, G.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z. J. Mater. Chem. C 2016, 4, 99.
[30] Tu, J.; Liu, F.; Wang, J.; Li, X.; Gong, Y.; Fan. Y.; Han, M.; Li, Q.; Li, Z. ChemPhotoChem 2019, 3, 133.
[31] Kokado, K.; Machida, T.; Iwasa, T.; Taketsugu, T.; Sada, K. J. Phys. Chem. C 2018, 122, 245.
[32] Wu, Y.; Yan, C.; Li, D.; Yuan, C.; Sun, J.; Zhou, S.; Zhang, H.; Shao, X. Chem.-Asian J. 2019, 14, 1860.
[33] Zhang, H.; Nie, Y.; Miao, J.; Zhang, D.; Li, Y.; Liu, G.; Sun, G.; Jiang, X. J. Mater. Chem. C 2019, 7, 3306.
[34] Xu, P.; Qiu, Q.; Ye, X.; Wei, M.; Xi, W.; Feng, H.; Qian, Z. Chem. Commun. 2019, 55, 14938.
[35] Xu, S.; Bai, X.; Ma, J.; Xu, M.; Hu, G.; James, T. D.; Wang, L. Anal. Chem. 2016, 88, 7853.
[36] Wu, H.; Jiang, Y.; Ding, Y.; Meng, Y.; Zeng, Z.; Cabanetos, C.; Zhou, G.; Gao, J.; Liu, J.; Roncali, J. Dyes Pigm. 2017, 146, 323.
[37] Cui, Y.; Yin, Y.; Cao, H.; Zhang, M.; Shan, G.; Sun, H.; Wu, Y.; Su, Z.; Xie, W. Dyes Pigm. 2015, 119, 62.
[38] Jadhav, T.; Choi, J. M.; Dhokale, B.; Mobin, S. M.; Lee, J. Y.; Misra, R. J. Phys. Chem. C 2016, 120, 18487.
[39] Jadhav, T.; Dhokale, B.;Patil, Y.; Mobin, S.; Misra, R. J. Phys. Chem. C 2016, 120, 24030.
[40] Weng, S.; Si, Z.; Zhou, Y.; Zuo, Q.; Shi, L.; Duan, Q. J. Lumin. 2018, 195, 14.
[41] Zhao, F.; Chen, Z.; Liu, G.; Fan, C.; Pu, S. Tetrahedron Lett. 2018, 59, 836.
[42] Zhu, X.; Wang, D.; Huang, H.; Zhang, X.; Wang, S.; Liu, R.; Zhu, H. Dyes Pigm. 2019, 171, 107657.
[43] Li, C.; Gong, W.; Hu, Z.; Aldred, M.; Zhang, G.; Chen, T.; Huang, Z.; Zhu, M. RSC Adv. 2013, 3, 8967
[44] Li, S.; Shang, Y.; Wang, L.; Kwok, R. T. K.; Tang, B. Z. J. Mater. Chem. C 2016, 4, 5363.
[45] Zhao, F.; Chen, Z.; Fan, C.; Liu, G.; Pu, S. Dyes Pigm. 2019, 164, 390.
[46] Yu, C.; Hsu, C.; Weng, H. RSC Adv. 2018, 8, 12619.
[47] Lusting, W.; Wang, F.; Teat, S.; Hu, Z.; Gong, Q.; Li, J. Inorg. Chem. 2016, 55, 7250.
[48] Wang, F.; Liu, W.; Teat, S.; Xu, F.; Wang, H.; Wang, X.; An, L.; Li, J. Chem. Commun. 2016, 52, 10249.
[49] Lusting, W.; Teat, S.; Li, J. J. Mater. Chem. C 2019, 7, 14739.
[50] Zhang, Z.; Lieu, T.; Wu, C.; Wang, X.; Wu, J.; Daugulis, O.; Miljanic, O. Chem. Commun. 2019, 55, 9387.
[51] Ma, S.; Ma, L.; Han, W.; Jiang, S.; Xu, B.; Tian, W. Sci. Sin. Chim. 2018, 48, 683(in Chinese). (马愫倩, 马莲, 韩文坤, 姜姗, 徐斌, 田文晶, 中国科学:化学, 2018, 48, 683.)
[52] Xu, B.; Tian, W. Aggregation-Induced Emission:Materials and Applications Volume 1, In ACS Symposium Series, Vol. 1226, Eds.:Fujiki, M.; Liu, B.; Tang, B. Z. American Chemical Society, Washington, DC, 2016, p. 113.
[53] Liu, W.; Wang, Y.; Sun, M.; Zhang, D.; Zheng, M.; Yang, W. Chem. Commun. 2013, 49, 6042.
[54] Liu, W.; Wang, Y.; Bu, L.; Li, J.; Sun, M.; Zhang, D.; Zheng, M.; Yang, C.; Xue, S.; Yang, W. J. Lumin. 2013, 143, 50.
[55] Dong, Y.; Xu, B.; Zhang, J.; Lu, H.; Wen, S.; Chen, F.; He, J.; Li, B.; Ye, L.; Tian, W. CrystEngComm 2012, 14, 6593.
[56] Wu, D.; Wang, M.; Luo, Y.; Zhang, Y.; Ma, Y.; Sun, B. New J. Chem. 2017, 41, 4220.
[57] Fang, W.; Zhang, G.; Chen, J.; Kong, L.; Yang, L.; Bi, H.; Yang, J. Sens. Actuators, B 2016, 229, 338.
[58] Martínez-Abadía, M.; Robles-Hernández, B.; Villacampa, B.; de la Fuente, M. R.; Giménez, R.; Ros, M. B. J. Mater. Chem. C 2015, 3, 3038.
[59] Seo, J.; Chung, J. W.; Cho, I.; Park, S. Y. Soft Matter 2012, 8, 7617.
[60] An, B.; Gierschner, J.; Park, S. Y. Acc. Chem. Res. 2012, 45, 544.
[61] Yeh, H.; Wu, W.; Wen, Y.; Wang, J.; Chen, C. J. Org. Chem. 2004, 69, 6455.
[62] Dou, C.; Han, L.; Zhao, S.; Zhang, H.; Wang, Y. J. Phys. Chem. Lett. 2011, 2, 666.
[63] Lim, S.; An, B.; Jung, S.; Chung, M.; Park, S. Angew. Chem., Int. Ed. 2004, 43, 6346.
[64] An, B.; Gihm, S.; Chung, J.; Park, C.; Kwon, S.; Park, S. J. Am. Chem. Soc. 2009, 131, 3950.
[65] Shin, S.; Gihm, S.; Park, C.; Kim, S.; Park, S. Chem. Mater. 2013, 25, 3288.
[66] Ma, C.; Zhang, X.; Yang, Y.; Ma, Z.; Yang, L.; Wu, Y.; Liu, H.; Jia, X.; Wei, Y. Dyes Pigm. 2016, 129,141.
[67] Ma, C.; Zhang, X.; Yang, L.; Li, Y.; Liu, H.; Yang, Y.; Xie, G.; Ou, Y.; Wei, Y. Dyes Pigm. 2017, 136, 85.
[68] Li, W.; Wang, Y.; Zhang, Y.; Gao, Y.; Dong, Y.; Zhang, X.; Song, Q.; Yang, B.; Ma, Y.; Zhang, C. J. Mater. Chem. C 2017, 5, 8097.
[69] Jyothi, M.; Annadhasan, M.; Vuppu, V.; Chandrasekar, R. Soft Matter 2020, 16, 2664.
[70] Javed, I.; Zhou, T.; Muhammd, F.; Guo, J.; Zhang, H.; Wang, Y. Langmuir 2012, 28,1439.
[71] Liu, J.; Li, W.; Liu, M.; Dong, Y.; Dai, Yu.; Song, Q.; Wang, J.; Zhang, C. Phys. Chem. Chem. Phys. 2018, 20, 28279
[72] Wang, Y.; Liu, J.; Yuan, W.; Wang, Y.; Zhou, H.; Liu, X.; Cao, J.; Zhang, C. Dyes Pigm. 2019, 167, 135.
[73] Kwon, M. S.; Gierschner, J.; Seo, J.; Park, S. Y. J. Mater. Chem. C 2014, 2, 2552.
[74] Kim, H. J.; Whang, D. R.; Gierschner, J.; Lee, C. H.; Park, S. Y. Angew. Chem., Int. Ed. 2015, 54, 4330.
[75] Xu, D.; Hao, J.; Gao, H.; Wang, Y.; Wang, Y.; Liu, X.; Han, A.; Zhang, C. Dyes Pigm. 2018, 150, 293.
[76] Wang, Y.; Xu, D.; Gao, H.; Wang, Y.; Liu, X.; Han, A.; Zhang, C.; Zang, L. J. Phys. Chem. C 2018, 122, 2297.
[77] Cheng, D.; Xu, D.; Wang, Y.; Zhou, H.; Zhou, Z.; Liu, X.; Han, A.; Zhang, C. Dyes Pigm. 2020, 173, 107937.
[78] Wang, Y.; Cheng, D.; Xu, D.; Zhou, H.; Liu, X.; Wang, Y.; Han, A.; Zhang, C. Dyes Pigm. 2019, 171, 107689.
[79] Cheng, D.; Xu, D.; Wang, Y.; Zhou, H.; Zhang, Y.; Liu, X.; Han, A.; Zhang, C. Dyes Pigm. 2020, 173, 107934.
[80] Zhang, Y.; Zhao, X.; Li, Y.; Wang, X.; Wang, Q.; Lu, H., Zhu, L. Dyes Pigm. 2019, 165, 53.
[81] Zhang, Y. X.; Fu, H.; Liu, D. E.; An, J. X.; Gao, H. J. Nanobiotechnol. 2019, 17, 104.
[82] Song, Y. K.; Lee, H.; Lee, C. K.; Choi, M. H.; Kim, C. J.; Lee, S.; Noh, S. M.; Park, Y. Appl. Surf. Sci. 2020, 511, 145556.
[83] Wang, F.; Li, X.; Wang, S.; Li, C.; Dong, H.; Ma, X.; Kim, S.; Cao, D. Chin. Chem. Lett. 2016, 27, 1592.
[84] Zhang, F.; Di, Y.; Li, Y.; Qi, Q.; Qian, J.; Fu, X.; Xu, B.; Tian, W. Dyes Pigm. 2017, 142, 491.
[85] Wang, Y.; Cheng, D.; Zhou, H.; Liu, J.; Liu, X.; Cao, J.; Han, A.; Zhang, C. Dyes Pigm. 2019, 171, 107739.
[86] Wang, Y.; Cheng, D.; Zhou, H.; Liu, J.; Liu, X.; Wang, Y.; Han, A.; Zhang, C. Dyes Pigm. 2019, 170, 107606.
[87] Xie, Z.; Yang, B.; Xie, W.; Liu, L.; Shen, F.; Wang, H.; Yang, X.; Wang, Z.; Li, Y.; Hanif, M.; Yang, G.; Ling, Ye.; Ma, Y. J. Phys. Chem. B 2006, 110, 20993.
[88] Shi, Z.; Davies, J.; Jang, S.; Kaminsky, W.; Jen, A. Chem. Commun. 2012, 48, 7880.
[89] Freudenberg, J.; Rominger, F.; Bunz, U. Chem.-Eur. J. 2015, 21, 16749.
[90] Freudenberg, J.; Rominger, F.; Bunz, U. Chem.-Eur. J. 2016, 22, 8740.
[91] Lu, H.; Su, F.; Mei, Q.; Tian, Y.; Tian, W.; Johnson, R. H.; Meldrum, D. R. J. Mater. Chem. 2012, 22, 9890.
[92] Lim, S.; An, B.; Park, S. Y. Macromolecules 2005, 38, 6236.
[93] Sinawang, G.; Wang, J.; Wu, B.; Wang, X.; He, Y. RSC Adv. 2016, 6, 12647.
[94] Zhao, Y.; Zhu, W.; Ren, L.; Zhang, K. Polym. Chem. 2016, 7, 5386.
[95] Wang, Q.; Chen, M.; Yao, B.; Wang, J.; Mei, J.; Sun, J. Z.; Qin, A.; Tang, B. Z. Macromol. Rapid Commun. 2013, 34, 796.
[96] Wu, Y.; He, B.; Quan, C.; Zheng, C.; Deng, H.; Hu, R.; Zhao, Z.; Huang, F.; Qin, A.; Tang, B. Z. Macromol. Rapid Commun. 2017, 38, 1700070.
[97] Li, W.; Che, C.; Pang, J.; Cao, Z.; Jiao, Y.; Xu, J.; Ren, Y.; Li, X. Langmuir 2018, 34, 5334.
[98] Li, W. T.; Zhang, H.; Li, X.; Yu, H.; Che, S. L.; Luan, S.; Ren, Y.; Li, S.; Liu, P.; Yu, X.; Li, X. ACS Appl. Mater. Interfaces 2020, 12, 7617.
[99] Mukherjee, S.; Thilagar, P. J. Mater. Chem. C 2016, 4, 2647.
[100] Mukherjee, S.; Thilagar, P. Chem. Commun. 2016, 52, 1070.
[101] Nunez, R.; Romero, I.; Teixidor, F.; Vinas, C. Chem. Soc. Rev. 2016, 45, 5147.
[102] Nunez, R.; Tarres, M.; FerrerUgalde, A.; de Biani, F. F.; Teixidor, F. Chem. Rev. 2016, 116, 14307.
[103] Tanaka, K.; Chujo, Y. In Principles and Applications of Aggregation-Induced Emission, Vol. 1, Eds.:Tang, B. Z.; Tang, Y., Springer Nature Switzerland AG, 2019, p. 27.
[104] Nie, Y.; Zhang, H.; Miao, J.; Zhao, X.; Li, Y.; Sun, G. J. Organomet. Chem. 2018, 865, 200.
[105] Kokado, K.; Chujo, Y. J. Org. Chem. 2011, 76, 316.
[106] Bae, H. J.; Kim, H.; Lee, K. M.; Kim, T.; Lee, Y. S.; Do, Y.; Lee, M. H. Dalton Trans. 2014, 43, 4978.
[107] Tu, D.; Pakkin, L.; Guo, S.; Lu, C.; Qiang, Z.; Yan, H. Angew. Chem., Int. Ed. 2017, 56, 11370.
[108] Chen, Y.; Guo, J.; Wu, X.; Jia, D.; Tong, F. Dyes Pigm. 2018, 148, 180.
[109] Wei, X.; Zhu, M.; Cheng, Z.; Lee, M.; Yan, H.; Lu, C.; Xu, J. Angew. Chem., Int. Ed. 2019, 58, 3162.
[110] Chen, L.; Wang, Y. H.; He, B.; Nie, H.; Hu, R.; Huang, F.; Qin, A.; Zhou, X. S.; Zhao, Z.; Tang, B. Z. Angew. Chem., Int. Ed. 2015, 54, 4231.
[111] Zhan G.; Liu, Z.; Bian, Z.; Huang, C. Front. Chem. 2019, 7, 305.
[112] Data, P.; Takeda, Y. Chem.-Asian J. 2019, 14, 1613.
[113] Yuan, W. Z.; Shen, X. Y.; Zhao, H.; Tang, B. Z. J. Phys. Chem. C 2010, 114, 6090.
[114] Gong, Y.; Tan, Y.; Li, H.; Zhang, Y.; Yuan, W.; Zhang, Y.; Sun, J.; Tang, B. Z. Sci. China:Chem. 2013, 56, 1183.
[115] Gong, Y.; Zhao, L.; Peng, Q.; Fan, D.; Yuan, W. Z.; Zhang, Y.; Tang, B. Z. Chem. Sci. 2015, 6, 4438.
[116] Zhao, W.; He, Z.; Lam, J.; Peng, Q.; Ma, H.; Shuai, Z.; Bai, G.; Hao, J.; Tang, B. Z. Chem. 2016, 1, 592.
[117] He, Z.; Zhao, W.; Lam, J.; Peng, Q.; Ma, H.; Liang, G.; Shuai, Z.; Tang, B. Z. Nat. Commun. 2017, 8, 416.
[118] Shimizu, M.; Kimura, A.; Sakaguchi, H. Eur. J. Org. Chem. 2016, 467.
[119] Yang, J.; Qin, J.; Geng, P.; Wang, J.; Fang, M.; Li, Z. Angew. Chem., Int. Ed. 2018, 57, 14174.
[120] Li, J.; Zhou, J.; Mao, Z.; Xie, Z.; Yang, Z.; Xu, B.; Liu, C.; Chen, X.; Ren, D.; Pan, H.; Shi, G.; Zhang, Y.; Chi, Z. Angew. Chem., Int. Ed. 2018, 57, 6449.
[121] Zhang, L.; Li, M.; Gao, Q.; Chen, C. Chin. J. Org. Chem. 2020, 40, 516(in Chinese). (张亮, 李猛, 高庆宇, 陈传峰, 有机化学, 2020, 40, 516.)
[122] Zhen, X.; Tao, Y.; An, Z.; Chen, P.; Xu, C.; Chen, R.; Huang, W.; Pu, K. Adv. Mater. 2017, 1606665.
[123] Yang, J.; Zhen, X.; Wang, B.; Gao, X.; Ren, Z.; Wang, J.; Xie, Y.; Li, J.; Peng, Q.; Pu, K.; Li, Z. Nat. Commun. 2018, 9, 840.
[124] Delgado, W.; Braun, C.; Boone, M.; Shynkaruk, O.; Qi, Y.; McDonald, R.; Ferguson, M.; Dara, P.; Almeida, S.; Aguiar, I.; Souza, G.; Alex, B.; He, G.; Rivard, E. ACS Appl. Mater. Interfaces 2018, 10, 12124.
[125] Koch, M.; Perumal, K.; Blacque, O.; Garg, J.; Saiganesh, R.; Kabilan, S.; Balasubramanian, K.; Venkatesan, K. Angew. Chem., Int. Ed. 2014, 53, 6378.
[126] Fang, M.; Yang, J.; Li, Z. Chin. J. Polym. Sci. 2019, 37, 383.
[127] DeRosa, C.; Kerr, C.; Fan, Z.; Kolpaczynska, M.; Mathew, A.; Evans, R.; Zhang, G.; Fraser, C. ACS Appl. Mater. Interfaces 2015, 7, 23633.
[128] Pramanik, S.; Bhalla, V.; Kumar, M. ACS Appl. Mater. Interfaces 2014, 6, 5930.
[129] Zhang, Y.; Han, T.; Gu, S.; Zhou, T.; Zhao, C.; Guo, Y.; Feng, X.; Tong, B.; Bing, J.; Shi, J.; Zhi, J.; Dong, Y. Chem.-Eur. J.2014, 20, 8856.
[130] Zhao, Y.; Lin, H.; Chen, M.; Yan, D. Ind. Eng. Chem. Res. 2014, 53, 3140.
[131] Ma, X.; Cheng, J.; Liu, J.; Zhou, X.; Xiang, H. New J. Chem. 2015, 39, 492.
[132] Yu, L.; Wu, Z.; Xie, G.; Zhong, C.; Zhu, Z.; Ma, D.; Yang, C. Chem. Commun. 2018, 54, 1379.
[133] Salini, P. S.; Derry Holaday, M. G.; Reddy, M. L.; Suresh, C. H.; Srinivasan, A. Chem. Commun. 2013, 49, 2213.
[134] Salini, P. S.; Thomas, A.; Sabarinathan, R.; Ramakrishnan, S.; Sreedevi, K.; Reddy, M.; Srinivasan, A. Chem.-Eur. J. 2011, 17, 6598.
[135] Karthik, G.; Krushna, P. V.; Srinivasan, A.; Chandrashekar, T. K. J. Org. Chem. 2013, 78, 8496.
[136] Ning, T.; Liu, L.; Jia, D.; Xie, X.; Wu, D. J. Photochem. Photobiol., A 2014, 291, 48.
[137] Zhang, Z.; Hashim, M. I.; Miljanic, O. S. Chem. Commun. 2017, 53, 10022.
[138] Shimizu, M.; Takeda, Y.; Higashi, M.; Hiyama, T. Angew. Chem., Int. Ed. Engl. 2009, 48, 3653.
[139] Chung, J.; An, B.; Hirato, F.; Kim, J.; Jinnai, H.; Park, S. J. Mater. Chem. 2010, 20, 7715.
[140] Wang, X.; He, D.; Huang, Y.; Fan, Q.; Wu, W.; Jiang, H. J. Org. Chem. 2018, 83, 5458.
[141] Keruckiene, R.; Guzauskas, M.; Narbutaitis, E.; Tsiko, U.; Volyniuk, D.; Chen, C.; Chiu, T.; Lin, C.; Lee, J.; Grazulevicius, J. V. Org. Electron. 2020, 78,105576.
[142] Kumari, N.; Naqvi, S.; Ahuja, M.; Bhardwaj, K.; Kumar, R. J. Mater. Sci.:Mater. Electron. 2020, 31, 4310.
[143] Chung, J. W.; Yoon, S. J.; Lim, S. J.; An, B. K.; Park, S. Y. Angew. Chem., Int. Ed. 2009, 48, 7030.
[144] Kim, J.; Chung, J.; Jung, Y.; Yoon, S.; An, B.; Huh, H.; Lee, O.; Park, S. J. Mater. Chem. 2010, 20, 10103.
[145] Chen, B.; Zhang, H.; Luo, W.; Nie, H.; Hu, R.; Qin, A.; Zhao, Z.; Tang, B. Z. J. Mater. Chem. C 2017, 5, 960.
[146] Guo, J.; Hu, S.; Luo, W.; Hu, R.; Qin, A.; Zhao, Z.; Tang, B. Z. Chem. Commun. 2017, 53, 1463
[147] Mallet, C.; Moussallem, C.; Faurie, A.; Allain, M.; Gohier, M.; Skene, W.; Frere, P. Chem.-Eur. J. 2015, 21, 7944.
[148] Yan, H.; Meng, X.; Li, B.; Ge, S.; Lu, Y. Dyes Pigm. 2017, 146, 479.
[149] Zhao, C.; Zhao, Y.; Pan, H.; Fu, G. Chem. Commun. 2011, 47, 5518.
[150] Liu, Y.; Zhang, Y.; Wu, X.; Lan, Q.; Chen, C.; Liu, S.; Chi, Z.; Jiang, L.; Chen, X.; Xu, J. J. Mater. Chem. C 2014, 2, 1068.
[151] Raju, T. B.; Gopikrishna, P.; Vaghasiya, J. V.; Soni, S. S.; Iyer, P. K. J. Photochem. Photobiol., A 2019, 376, 12.
[152] Ni, S.; Min, T.; Li, Y.; Zha, M.; Zhang, P.; Ho, C.; Li, K. Angew. Chem., Int. Ed. 2020, 132, 10265.
[153] Wang, S.; Wamg, F.; Li, C.; Li, T.; Cao, D.; Ma, X. Sci. China:Chem. 2018, 61, 1301.
[154] Morita, M.; Yamada, S.; Konno, T. New J. Chem. 2020, 44, 6704.
[155] Hu, M.; Feng, H.; Yuan, Y.; Zheng, Y.; Tang, B. Z. Coord. Chem. Rev. 2020, 416, 213329.
[156] Shen, G.; Gou, F.; Cheng, J.; Zhang, X.; Zhou, X.; Xiang, H. RSC Adv. 2017, 7, 40640.
[157] Song, F.; Xu, Z.; Zhang, Q.; Zhao, Z.; Zhang, H.; Zhao, W.; Qiu, Z.; Qi, C.; Zhang, H.; Sung, H.; Williams, I.; Lam, J.; Zhao, Z.; Qin, A.; Ma, D.; Tang, B. Z. Adv. Funct. Mater. 2018, 23, 180051.
[158] Zhao, N.; Gao, W.; Zhang, M.; Yang, J.; Zheng, X.; Li, Y.; Cui, R.; Yin, W.; Li, N. Mater. Chem. Front. 2019, 3, 1613.
[159] Li, X.; Shi, X.; Li, X.; Shi, D. Beilstein J. Org. Chem. 2019, 15, 2213.
[160] Gouverneur, V.; Szpera, R.; Moseley, D.; Smith, B.; Sterling, A. Angew. Chem., Int. Ed. 2019, 58, 14828.
[161] He, J.; Lou, S.; Xu, D. Chin. J. Org. Chem. 2016, 36, 1218(in Chinese). (何将旗, 娄绍杰, 许丹倩, 有机化学, 2016, 36, 1218.)
[162] Yang, J.; Li, Z. Chin. J. Org. Chem. 2019, 39, 3304(in Chinese). (杨杰, 李振, 有机化学, 2019, 39, 3304).
[163] Yang, J.; Chi, Z.; Zhu, W.; Tang, B. Z.; Li, Z. Sci. China:Chem. 2019, 62, 1090.
[164] Zhang, J.; Liu, H.; Meng, L. Chin. J. Org. Chem. 2019, 39, 3132(in Chinese). (张继东, 刘鸿泽, 孟丽, 有机化学, 2019, 39, 3132).
[165] Guan, X.; Li, Z.; Wang, L.; Liu, M.; Wang, K.; Yang, X.; Li, Y.; Hu, L.; Zhao, X.; Lai, S.; Lei, Z. Acta Chim. Sinica 2019, 77, 1268(in Chinese). (关晓琳, 李志飞, 王林, 刘美娜, 王凯龙, 杨学琴, 李亚丽, 胡丽丽, 赵小龙, 来守军, 雷自强, 化学学报, 2019, 77, 1268.)

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