Full-color-tunable chiral aggregation-induced emission fluorophores with tailored propeller chirality and their circularly polarized luminescence

Abstract

The regulation of emission color, emission efficiency, and asymmetry factor is of great significance for the real applications of circularly polarized luminescent (CPL) materials. Herein, we develop a modular synthetic strategy toward full-color-tunable CPL materials based on chiral macrocyclic aggregation-induced emission (AIE) luminogens via delicate molecular engineering. Modular synthesis of chiral AIEgens with different acceptor moieties has afforded a series of bright solid emitters with tunable emission colors. These chiral cyclic AIEgens have retained high solid-state emission quantum yield and displayed CPL emission from blue to red as nanoaggregates, in liquid crystal matrix and polymer film. The strong acceptor units in the red-emitting chiral AIEgens RBTPE-2CN and SBTPE-2CN have rendered them twisted intramolecular charge transfer properties and solvatochromic luminescence. And polymer matrix with different polarity further facilitates the tuning of CPL emission color from green to red emission. These results have paved a reliable approach toward constructing full-spectra solid-state CPL material.

Keywords

aggregation-induced emission / chiral macrocycles / chirality / circularly polarized luminescence / full-color tunable

References

[1] S. Yang, S. Zhang, F. Hu, J. Han, F. Li, Coord. Chem. Rev. 2023, 485, 215116.

[2] D. Han, C. Li, C. Jiang, X. Jin, X. Wang, R. Chen, J. Cheng, P. Duan, Aggregate 2022, 3, e148.

[3] C. Liu, J.-C. Yang, J. W. Y. Lam, H.-T. Feng, B. Z. Tang, Chem. Sci. 2022, 13, 611.

[4] Y. Deng, M. Wang, Y. Zhuang, S. Liu, W. Huang, Q. Zhao, Light Sci. Appl. 2021, 10, 76.

[5] Y. Sang, J. Han, T. Zhao, P. Duan, M. Liu, Adv. Mater. 2020, 32, 1900110.

[6] X. Yang, X. Gao, Y.-X. Zheng, H. Kuang, C.-F. Chen, M. Liu, P. Duan, Z. Tang, CCS Chem. 2023, 5, 2760.

[7] Z.-L. Gong, X. Zhu, Z. Zhou, S.-W. Zhang, D. Yang, B. Zhao, Y.-P. Zhang, J. Deng, Y. Cheng, Y.-X. Zheng, S.-Q. Zang, H. Kuang, P. Duan, M. Yuan, C.-F. Chen, Y. S. Zhao, Y.-W. Zhong, B. Z. Tang, M. Liu, Sci. China Chem. 2021, 64, 2060.

[8] C. Zhang, S. Li, X.-Y. Dong, S.-Q. Zang, Aggregate 2021, 2, e48.

[9] Y. Wu, M. Li, Z.-g. Zheng, Z.-Q. Yu, W.-H. Zhu, J. Am. Chem. Soc. 2023, 145, 12951.

[10] S. Hu, L. Hu, X. Zhu, Y. Wang, M. Liu, Angew. Chem. Int. Ed. 2021, 60, 19451.

[11] Y.-J. Kong, Z.-P. Yan, S. Li, H.-F. Su, K. Li, Y.-X. Zheng, S.-Q. Zang, Angew. Chem. Int. Ed. 2020, 59, 5336.

[12] W.-L. Zhao, Y.-F. Wang, S.-P. Wan, H.-Y. Lu, M. Li, C.-F. Chen, CCS Chem. 2022, 4, 3540.

[13] H. Yan, Y. He, D. Wang, T. Han, B. Z. Tang, Aggregate 2023, 4, e331.

[14] F. Gan, C. Shen, H. Qiu, in Handbook of Aggregation-Induced Emission, 2022, pp. 27.

[15] J. Yang, M. Fang, Z. Li, Aggregate 2020, 1, 6.

[16] Q. Liu, Q. Xia, Y. Xiong, B. S. Li, B. Z. Tang, Macromolecules 2020, 53, 6288.

[17] M. Hu, H.-T. Feng, Y.-X. Yuan, Y.-S. Zheng, B. Z. Tang, Coord. Chem. Rev. 2020, 416, 213329.

[18] N. Lu, X. Gao, M. Pan, B. Zhao, J. Deng, Macromolecules 2020, 53, 8041.

[19] J. Liu, H. Su, L. Meng, Y. Zhao, C. Deng, J. C. Y. Ng, P. Lu, M. Faisal, J. W. Y. Lam, X. Huang, H. Wu, K. S. Wong, B. Z. Tang, Chem. Sci. 2012, 3, 2737.

[20] H. Li, J. Cheng, Y. Zhao, J. W. Y. Lam, K. S. Wong, H. Wu, B. S. Li, B. Z. Tang, Mater. Horiz. 2014, 1, 518.

[21] Y. Wu, L. H. You, Z.-Q. Yu, J.-H. Wang, Z. Meng, Y. Liu, X.-S. Li, K. Fu, X.-K. Ren, B. Z. Tang, ACS Mater. Lett. 2020, 2, 505.

[22] Y. Wu, C. Yan, X.-S. Li, L. H. You, Z.-Q. Yu, X. Wu, Z. Zheng, G. Liu, Z. Guo, H. Tian, W.-H. Zhu, Angew. Chem. Int. Ed. 2021, 60, 24549.

[23] Y. Zhang, H. Li, Z. Geng, W.-H. Zheng, Y. Quan, Y. Cheng, ACS Nano 2022, 16, 3173.

[24] S. Huo, P. Duan, T. Jiao, Q. Peng, M. Liu, Angew. Chem. Int. Ed. 2017, 56, 12174.

[25] Y. Shi, P. Duan, S. Huo, Y. Li, M. Liu, Adv. Mater. 2018, 30, 1705011.

[26] H. Shang, Z. Ding, Y. Shen, B. Yang, M. Liu, S. Jiang, Chem. Sci. 2020, 11, 2169.

[27] B. Zhao, X. Gao, N. Lu, J. Deng, Adv. Opt. Mater. 2020, 8, 2000858.

[28] Y.-X. Yuan, J.-H. Jia, Y.-P. Song, F.-Y. Ye, Y.-S. Zheng, S.-Q. Zang, J. Am. Chem. Soc. 2022, 144, 5389.

[29] F. Wang, C. Shen, F. Gan, G. Zhang, H. Qiu, CCS Chem. 2023, 5, 1592.

[30] M. Kemper, E. Engelage, C. Merten, Angew. Chem. Int. Ed. 2021, 60, 2958.

[31] S. Lin, Y. Tang, W. Kang, H. K. Bisoyi, J. Guo, Q. Li, Nat. Commun. 2023, 14, 3005.

[32] M. Hu, F.-Y. Ye, C. Du, W. Wang, T.-T. Zhou, M.-L. Gao, M. Liu, Y.-S. Zheng, ACS Nano 2021, 15, 16673.

[33] A. Ji, H. Lou, C. Qu, W. Lu, Y. Hao, J. Li, Y. Wu, T. Chang, H. Chen, Z. Cheng, Nat. Commun. 2022, 13, 3815.

[34] T. Goto, Y. Okazaki, M. Ueki, Y. Kuwahara, M. Takafuji, R. Oda, H. Ihara, Angew. Chem. Int. Ed. 2017, 56, 2989.

[35] Y. Zuo, J. Liu, P. Li, K. Li, J. W. Y. Lam, D. Wu, B. Z. Tang, Cell Rep. Phys. Sci. 2023, 4, 101202.

[36] D. Li, R. Hu, D. Guo, Q. Zang, J. Li, Y. Wang, Y.-S. Zheng, B. Z. Tang, H. Zhang, J. Phys. Chem. C 2017, 121, 20947.

[37] X. Liu, P. Lei, X. Liu, Y. Li, Y. Wang, L. Wang, Q. Zeng, Y. Liu, Poly. Chem. 2023, 14, 2979.

[38] X. Liu, Z. Shi, F. Yu, C. Teng, C. Zhang, Z.-R. Chen, Aggregate 2023, 4, e363.

[39] H. Qu, Y. Wang, Z. Li, X. Wang, H. Fang, Z. Tian, X. Cao, J. Am. Chem. Soc. 2017, 139, 18142.

[40] J.-B. Xiong, H.-T. Feng, J.-P. Sun, W.-Z. Xie, D. Yang, M. Liu, Y.-S. Zheng, J. Am. Chem. Soc. 2016, 138, 11469.

[41] M. Hu, F.-Y. Ye, C. Du, W. Wang, W. Yu, M. Liu, Y.-S. Zheng, Angew. Chem. Int. Ed. 2022, 61, e202115216.

[42] Y. Wang, X. Liu, H. Li, X. Liu, L. Wang, Y. Liu, Chin. J. Chem. 2022, 40, 2393.

[43] Y. Wang, L. Cui, Y. Wang, F. Li, Y. Li, Q. Meng, Chem. Eur. J. 2023, 29, e202302373.

[44] Q. Meng, L. Cui, Q. Liao, J. Xu, Y. Wang, Chem. Commun. 2022, 58, 10384.

[45] G. J. Bodwell, P. R. Nandaluru, Isr. J. Chem. 2012, 52, 105.

[46] X. Liu, Y. Wang, X. Liu, S. Liu, Y. Li, L. Wang, Y. Liu, Poly. Chem. 2022, 13, 6197.

[47] S. Sasaki, G. P. C. Drummen, G.-i. Konishi, J. Mater. Chem. C 2016, 4, 2731.

[48] H. Zhang, X. Zheng, R. T. K. Kwok, J. Wang, N. L. C. Leung, L. Shi, J. Z. Sun, Z. Tang, J. W. Y. Lam, A. Qin, B. Z. Tang, Nat. Commun. 2018, 9, 4961.

[49] L. Di Bari, G. Pescitelli, P. Salvadori, J. Am. Chem. Soc. 1999, 121, 7998.

[50] T. Kimoto, N. Tajima, M. Fujiki, Y. Imai, Chem. Asian J. 2012, 7, 2836.

[51] T. Zhao, J. Han, X. Jin, Y. Liu, M. Liu, P. Duan, Angew. Chem. Int. Ed. 2019, 58, 4978.

[52] H. Hayasaka, T. Miyashita, M. Nakayama, K. Kuwada, K. Akagi, J. Am. Chem. Soc. 2012, 134, 3758.

[53] T. Kimoto, T. Amako, N. Tajima, R. Kuroda, M. Fujiki, Y. Imai, Asian J. Org. Chem. 2013, 2, 404.

[54] Y. Zhang, J. Wang, H. Chen, M. Lin, Chin. Chem. Lett. 2022, 33, 2473.

[55] Q. Ye, F. Zheng, E. Zhang, H. K. Bisoyi, S. Zheng, D. Zhu, Q. Lu, H. Zhang, Q. Li, Chem. Sci. 2020, 11, 9989.

[56] D. Niu, Y. Jiang, L. Ji, G. Ouyang, M. Liu, Angew. Chem. Int. Ed. 2019, 58, 5946.

[57] H. Zhang, C. Yang, S. Shan, L. Wen, D. Chen, G. Zou, ACS Appl. Mater. Interfaces 2022, 14, 36157.

[58] F. Wang, W. Ji, P. Yang, C.-L. Feng, ACS Nano 2019, 13, 7281.

[59] D. Niu, L. Ji, G. Ouyang, M. Liu, ACS Appl. Mater. Interfaces 2020, 12, 18148.

[60] M. P. Aldred, C. Li, M.-Q. Zhu, Chem. Eur. J. 2012, 18, 16037.

[61] S. Ma, S. Du, G. Pan, S. Dai, B. Xu, W. Tian, Aggregate 2021, 2, e96.

[62] J. Voskuhl, M. Giese, Aggregate 2022, 3, e124.

RIGHTS & PERMISSIONS

2024 The Author(s). Aggregate published by SCUT, AIEI, and John Wiley & Sons Australia, Ltd.