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Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds

  • Yunle Lu ,
  • Yanjie Wang ,
  • Liangliang Zhu ,
  • Bingbing Yue
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  • aSchool of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
    bState Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438

Received date: 2022-04-25

  Revised date: 2022-06-22

  Online published: 2022-07-21

Supported by

Shanghai Sailing Program(20YF1432400); National Natural Science Foundation of China(22105128)

Abstract

Aggregation-induced emission (AIE) has received extensive attention in the field of optical materials since its discovery. Organic phosphorescence with high efficiency and long lifetime exhibits excellent luminescent properties and high flexibility of modification, which is an important development direction of organic light-emitting materials in the future. Persulfurated arenes as a typical class of aggregation-induced phosphorescence (AIP) materials possess highly twistable molecular structures and abundant modification sites. Therefore, a number of luminescent systems (such as solution state, thin film state, crystalline state, etc.) based on these compounds have been developed. At the same time, persulfurated arene exhibit a unique molecular conformation transition in the excited state, which not only provides a theoretical basis for the regulation of molecular self-assembly morphology and luminescence properties under in situ photocontrol, but also builds a fabulous platform for developing abundant luminescence systems. This paper aims to summarize the aggregation induced phosphorescence properties of different series of persulfurated arenes under various regulation modes. Combined with the research practice of our research group in this field, the AIP properties of persulfurated arenes in recent years are reviewed. The possible problems in the current research are briefly prospected, hoping to provide some reference and thinking for the future development direction of AIP materials.

Cite this article

Yunle Lu , Yanjie Wang , Liangliang Zhu , Bingbing Yue . Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3549 -3561 . DOI: 10.6023/cjoc202204063

References

[1]
Sagara, Y.; Kato, T. Nat. Chem. 2009, 1, 605.
[2]
Hsu, C.-W.; Lin, C.-C.; Chung, M.-W.; Chi, Y.; Lee, G.-H.; Chou, P.-T.; Chang, C.-H.; Chen, P.-Y. J. Am. Chem. Soc. 2011, 133, 12085.
[3]
Xu, S.; Chen, R.; Zheng, C.; Huang, W. Adv. Mater. 2016, 28, 9920.
[4]
Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361.
[5]
Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740.
[6]
Liu, J.; Lam, J. W. Y.; Tang, B. Z. J. Inorg. Organomet. Polym. 2009, 19, 249.
[7]
Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009, 4332.
[8]
Lu, H.; Zheng, Y.; Zhao, X.; Wang, L.; Ma, S.; Han, X.; Xu, B.; Tian, W.; Gao, H. Angew. Chem., Int. Ed. Engl, 2016, 55, 155.
[9]
Cai, X.; Liu, B. Angew. Chem., Int. Ed. 2020, 59, 9868.
[10]
Hu, R.; Yang, X.; Qin, A.; Tang, B. Z. Mater. Chem. Front. 2021, 5, 4073.
[11]
Feng, X. C.; Zhu, L. L.; Yue, B. B. Acta Chim. Sinica 2022, 80, 647. (in Chinese)
[11]
( 冯锡成, 朱亮亮, 岳兵兵, 化学学报 2022, 80, 647.)
[12]
Han, P. B.; Xu, H.; An, Z. F.; Cai, Z. Y.; Cai, Z. X.; Chao, H.; Chen, B.; Chen, M.; Chen, Y.; Chi, Z. G,.; Dai, S. D.; Ding, D.; Dong, Y. P.; Gao, Z. Y.; Guan, W. J.; He, Z. K.; Hu, J. J.; Hu, R.; Hu, Y. X.; Huang, Q. Y.; Kang, M. M.; Li, D. X.; Li, J. S.; Li, S. Z.; Li, W. L.; Li, Z.; Lin, X. L.; Liu, H. Y.; Liu, P. Y.; Lou, X. D.; Lu, C.; Ma, D. G.; Ou, H. L.; Ouyang, J.; Peng, Q.; Qian, J.; Qin, A. J.; Qu, J. M.; Shi, J. B.; Shuai, Z. G.; Sun, L. H.; Tian, R.; Tian, W. J.; Tong, B.; Wang, H. L.; Wang, D.; Wang, H.; Wang, T.; Wang, X.; Wang, Y. C.; Wu, S. Z.; Xia, F.; Xie, Y. J.; Xiong, K.; Xu, B.; Yan, D. P.; Yang, H. B.; Yang, Q. Z.; Yang, Z. Y.; Yuan, L. Z.; Yuan, W. Z.; Zang, S. Q.; Zeng, F.; Zeng, J. J.; Zeng, Z.; Zhang, G. Q.; Zhang, X. Y.; Zhang, X. P.; Zhang, Y.; Zhang, Y. F.; Zhang, Z. J.; Zhao, J.; Zhao, Z.; Zhao, Z. H.; Zhao, Z. J.; Tang, B. Z. Prog. Chem. 2022, 34, 1. (in Chinese)
[12]
( 韩鹏博, 徐赫, 安众福, 蔡哲毅, 蔡政旭, 巢晖, 陈彪, 陈明, 陈禹, 池振国, 代淑婷, 丁丹, 董宇平, 高志远, 管伟江, 何自开, 胡晶晶, 胡蓉, 胡毅雄, 黄秋忆, 康苗苗, 李丹霞, 李济森, 李树珍, 李文朗, 李振, 林新霖, 刘骅莹, 刘佩颖, 娄筱叮, 吕超, 马东阁, 欧翰林, 欧阳娟, 彭谦, 钱骏, 秦安军, 屈佳敏, 石建兵, 帅志刚, 孙立和, 田锐, 田文晶, 佟斌, 汪辉亮, 王东, 王鹤, 王涛, 王晓, 王誉澄, 吴水珠, 夏帆, 谢育俊, 熊凯, 徐斌, 闫东鹏, 杨海波, 杨清正, 杨志涌, 袁丽珍, 袁望章, 臧双全, 曾钫, 曾嘉杰, 曾卓, 张国庆, 张晓燕, 张学鹏, 张艺, 张宇凡, 张志军, 赵娟, 赵征, 赵子豪, 赵祖金, 唐本忠, 化学进展 2022, 34, 1.)
[13]
Zhang, L. L.; Wang, Y. Y.; Zhu, G. N.; Dai, W. B.; Zhao, Z. X.; Zhao, Y.; Zhi, J. G.; Dong, Y. P. Acta Chim. Sinica 2022, 80, 282. (in Chinese)
[13]
( 张璐璐, 王媛媛, 朱贵楠, 戴文博, 赵紫璇, 赵盈, 支俊格, 董宇平, 化学学报 2022, 80, 282.)
[14]
Tsang, M.-K.; Bai, G.; Hao, J. Chem. Soc. Rev. 2015, 44, 1585.
[15]
Qi, Y.; Ding, N.; Wang, Z.; Xu, L.; Fang, Y. ACS Appl. Mater. Interfaces 2019, 11, 8676.
[16]
Ma, Z.; Wang, Z.; Teng, M.; Xu, Z.; Jia, X. ChemPhysChem 2015, 16, 1811.
[17]
Huang, L.; Qian, C.; Ma, Z. Chem.-Eur. J. 2020, 26, 11914.
[18]
Xie, Y.; Li, Z. Mater. Chem. Front. 2020, 4, 317.
[19]
Cai, S.; Shi, H.; Tian, D.; Ma, H.; Cheng, Z.; Wu, Q.; Gu, M.; Huang, L.; An, Z.; Peng, Q. Adv. Funct. Mater. 2018, 28, 1705045
[20]
Shi, H.; Song, L.; Ma, H.; Sun, C.; Huang, K.; Lv, A.; Ye, W.; Wang, H.; Cai, S.; Yao, W.; Zhang, Y.; Zheng, R.; An, Z.; Huang, W. J. Phys. Chem. Lett. 2019, 10, 595.
[21]
Shi, H.; An, Z.; Li, P.-Z.; Yin, J.; Xing, G.; He, T.; Chen, H.; Wang, J.; Sun, H.; Huang, W.; Zhao, Y. Cryst. Growth Des. 2016, 16, 808.
[22]
Shoji, Y.; Ikabata, Y.; Wang, Q.; Nemoto, D.; Sakamoto, A.; Tanaka, N.; Seino, J.; Nakai, H.; Fukushima, T. J. Am. Chem. Soc. 2017, 139, 2728.
[23]
An, Z.; Zheng, C.; Tao, Y.; Chen, R.; Shi, H.; Chen, T.; Wang, Z.; Li, H.; Deng, R.; Liu, X.; Huang, W. Nat. Mater. 2015, 14, 685.
[24]
Gong, Y.; Chen, G.; Peng, Q.; Yuan, W. Z.; Xie, Y.; Li, S.; Zhang, Y.; Tang, B. Z. Adv. Mater. 2015, 27, 6195.
[25]
Zhao, W.; He, Z.; Lam, J. W. Y.; Peng, Q.; Ma, H.; Shuai, Z.; Bai, G.; Hao, J.; Tang, B. Z. Chem 2016, 1, 592.
[26]
Reineke, S.; Seidler, N.; Yost, S. R.; Prins, F.; Tisdale, W. A.; Baldo, M. A. Appl. Phys. Lett. 2013, 103, 093302.
[27]
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.
[28]
Zhao, Y.; Yang, X. G.; Lu, X. M.; Yang, C. D.; Fan, N. N.; Yang, Z. T.; Wang, L. Y.; Ma, L. F. Inorg. Chem. 2019, 58, 6215.
[29]
Niembro, S.; Vallribera, A.; Moreno-Ma?as, M. New J. Chem. 2008, 32, 94.
[30]
Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927.
[31]
Bergamini, G.; Fermi, A.; Botta, C.; Giovanella, U.; Di Motta, S.; Negri, F.; Peresutti, R.; Gingras, M.; Ceroni, P. J. Mater. Chem. C 2013, 1, 2717.
[32]
Fermi, A.; Bergamini, G.; Roy, M.; Gingras, M.; Ceroni, P. J. Am. Chem. Soc. 2014, 136, 6395.
[33]
MacNicol, D. D.; Mallinson, P. R.; Robertson, C. D. J. Chem. Soc., Chem. Commun. 1985, 1649.
[34]
Jia, X.; Yue, B.; Zhou, L.; Niu, X.; Wu, W.; Zhu, L. Chem. Commun. 2020, 56, 4336.
[35]
Villa, M.; Roy, M.; Bergamini, G.; Gingras, M.; Ceroni, P. Dalton Trans. 2019, 48, 3815.
[36]
Rocklin, A. L. J. Org. Chem. 1956, 21, 1478.
[37]
Kulka, M. J. Org. Chem. 1959, 24, 235.
[38]
Langille, K. R.; Peach, M. E. J. Fluorine Chem. 1972, 1, 407.
[39]
MacNicol, D. D.; Mallison, P. R.; Murphy, A.; Sym, G. J. Tetrahedron Lett. 1982, 23, 4131.
[40]
Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812.
[41]
Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis 1983, 751.
[42]
Maiolo, F.; Testaferri, L.; Tiecco, M.; Tingoli, M. J. Org. Chem. 1981, 46, 3070.
[43]
Villa, M.; Del Secco, B.; Ravotto, L.; Roy, M.; Rampazzo, E.; Zaccheroni, N.; Prodi, L.; Gingras, M.; Vinogradov, S. A.; Ceroni, P. J. Phys. Chem. C 2019, 123, 29884.
[44]
Chen, G.; Zhou, Z.; Feng, H.; Zhang, C.; Wang, Y.; Qian, Z.; Pan, J. Chem. Commun. 2019, 55, 4841.
[45]
Wu, H.; Chen, Z.; Chi, W.; Bindra, A. K.; Gu, L.; Qian, C.; Wu, B.; Yue, B.; Liu, G.; Yang, G.; Zhu, L.; Zhao, Y. Angew. Chem., Int. Ed. 2019, 58, 11419.
[46]
Li, X.; Baryshnikov, G.; Ding, L.; Bao, X.; Li, X.; Lu, J.; Liu, M.; Shen, S.; Luo, M.; Zhang, M.; ?gren, H.; Wang, X.; Zhu, L. Angew. Chem., Int. Ed. 2020, 59, 7548.
[47]
Luo, M.; Li, X.; Ding, L.; Baryshnikov, G.; Shen, S.; Zhu, M.; Zhou, L.; Zhang, M.; Lu, J.; Agren, H.; Wang, X. D.; Zhu, L. Angew. Chem., Int. Ed. 2020, 59, 17018.
[48]
Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 8, 747.
[49]
Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Acc. Chem. Res. 2013, 46, 2441.
[50]
Jia, X.; Shao, C.; Bai, X.; Zhou, Q.; Wu, B.; Wang, L.; Yue, B.; Zhu, H.; Zhu, L. Proc. Natl. Acad. Sci. U. S. A. 2019, 116, 4816.
[51]
Gu, J.; Yue, B.; Baryshnikov, G. V.; Li, Z.; Zhang, M.; Shen, S.; ?gren, H.; Zhu, L. Research 2021, 9862093.
[52]
Zhang, G.; Chen, J.; Payne, S. J.; Kooi, S. E.; Demas, J. N.; Fraser, C. L. J. Am. Chem. Soc. 2007, 129, 8942.
[53]
Morris, W. A.; Sabat, M.; Butler, T.; DeRosa, C. A.; Fraser, C. L. J. Phys. Chem. C 2016, 120, 14289.
[54]
Wu, H.; Hang, C.; Li, X.; Yin, L.; Zhu, M.; Zhang, J.; Zhou, Y.; ?gren, H.; Zhang, Q.; Zhu, L. Chem. Commun. 2017, 53, 2661.
[55]
Wu, H.; Zhou, Y.; Yin, L.; Hang, C.; Li, X.; ?gren, H.; Yi, T.; Zhang, Q.; Zhu, L. J. Am. Chem. Soc. 2017, 139, 785.
[56]
Li, M.; Li, S.-H.; Zhang, D.; Cai, M.; Duan, L.; Fung, M.-K.; Chen, C.-F. Angew. Chem., Int. Ed. 2018, 57, 2889.
[57]
Song, F.; Xu, Z.; Zhang, Q.; Zhao, Z.; Zhang, H.; Zhao, W.; Qiu, Z.; Qi, C.; Zhang, H.; Sung, H. H. Y.; Williams, I. D.; Lam, J. W. Y.; Zhao, Z.; Qin, A.; Ma, D.; Tang, B. Z. Adv. Funct. Mater. 2018, 28, 1800051.
[58]
Sun, S.; Wang, J.; Chen, L.; Chen, R.; Jin, J.; Chen, C.; Chen, S.; Xie, G.; Zheng, C.; Huang, W. J. Mater. Chem. C 2019, 7, 14511.
[59]
Zinna, F.; Giovanella, U.; Bari, L. D. Adv. Mater. 2015, 27, 1791.
[60]
Wang, Y.; Li, Q. Adv. Mater. 2012, 24, 1926.
[61]
Qiu, Y.; Chen, P.; Guo, P.; Li, Y.; Liu, M. Adv. Mater. 2008, 20, 2908.
[62]
Hayasaka, H.; Miyashita, T.; Nakayama, M.; Kuwada, K.; Akagi, K. J. Am. Chem. Soc. 2012, 134, 3758.
[63]
Canary, J. W. Chem. Soc. Rev. 2009, 38, 747.
[64]
Zong, Z.; Zhang, P.; Qiao, H.; Hao, A.; Xing, P. J. Mater. Chem. 2020, 8, 16224.
[65]
Malik, A. U.; Gan, F.; Shen, C.; Yu, N.; Wang, R.; Crassous, J.; Shu, M.; Qiu, H. J. Am. Chem. Soc. 2018, 140, 2769.
[66]
Tang, X.; Chu, D.; Jiang, H.; Gong, W.; Jiang, C.; Cui, Y.; Liu, Y. Mater. Chem. Front. 2020, 4, 2772.
[67]
Zhu, H.; Li, Q.; Shi, B.; Xing, H.; Sun, Y.; Lu, S.; Shangguan, L.; Li, X.; Huang, F.; Stang, P. J. J. Am. Chem. Soc. 2020, 142, 17340.
[68]
Jiang, Q.; Xu, X.; Yin, P.-A.; Ma, K.; Zhen, Y.; Duan, P.; Peng, Q.; Chen, W.-Q.; Ding, B. J. Am. Chem. Soc. 2019, 141, 9490.
[69]
Górecki, M.; Zinna, F.; Biver, T.; Di Bari, L. J. Pharm. Biomed. Anal. 2017, 144, 6.
[70]
Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. 2004, 43, 4490.
[71]
Kawasaki, T.; Sato, M.; Ishiguro, S.; Saito, T.; Morishita, Y.; Sato, I.; Nishino, H.; Inoue, Y.; Soai, K. J. Am. Chem. Soc. 2005, 127, 3274.
[72]
Chen, W.; Ma, K.; Duan, P.; Ouyang, G.; Zhu, X.; Zhang, L.; Liu, M. Nanoscale 2020, 12, 19497.
[73]
Jin, X.; Sang, Y.; Shi, Y.; Li, Y.; Zhu, X.; Duan, P.; Liu, M. ACS Nano 2019, 13, 2804.
[74]
Wu, B.; Wu, H.; Gong, Y.; Li, A.; Jia, X.; Zhu, L. J. Mater. Chem. C 2021, 9, 4275.
[75]
Fermi, A.; Bergamini, G.; Peresutti, R.; Marchi, E.; Roy, M.; Ceroni, P.; Gingras, M. Dyes Pigm. 2014, 110, 113.
[76]
Weng, T.; Zou, Q.; Zhang, M.; Wu, B.; Baryshnikov, G. V.; Shen, S.; Chen, X.; ?gren, H.; Jia, X.; Zhu, L. J. Phys. Chem. Lett. 2021, 12, 6182.
[77]
Hu, X.; Zhao, X.; He, B.; Zhao, Z.; Zheng, Z.; Zhang, P.; Shi, X.; Kwok, R. T.; Lam, J. W.; Qin, A. Research 2018, 2018, 3152870.
[78]
Ejaz, A.; Han, J. H.; Dahiya, R. J. Colloid Interface Sci. 2020, 570, 322.
[79]
?l?czkowski, M. L.; Mabesoone, M. F.; ?l?czkowski, P.; Palmans, A. R.; Meijer, E. Nat. Chem. 2021, 13, 200.
[80]
Lee, C.; Choi, C. H.; Joo, T. Phys. Chem. Chem. Phys. 2020, 22, 1115.
[81]
Mayor, M.; Lehn, J.-M. Helv. Chim. Acta 1997, 80, 2277.
[82]
Xu, J.; Feng, H.; Teng, H.; Chen, G.; Pan, S.; Chen, J.; Qian, Z. Chem. Eur. J. 2018, 24, 12773.
[83]
Shen, S.; Baryshnikov, G.; Yue, B.; Wu, B.; Li, X.; Zhang, M.; ?gren, H.; Zhu, L. J. Mater. Chem. C 2021, 9, 11707.
[84]
Wu, H.; Zhao, P.; Li, X.; Chen, W.; ?gren, H.; Zhang, Q.; Zhu, L. ACS Appl. Mater. Interfaces 2017, 9, 3865.
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