10.1002/anie.202001103
Angewandte Chemie International Edition
RESEARCH ARTICLE
[4] a) Y. Chen, J. W. Y. Lam, R. T. K. Kwok, B. Liu, B. Z. Tang, Mater. Horiz.
2019, 6, 428−433; b) Y. Chen, W. Zhang, Z. Zhao, Y. Cai, J. Gong, R. T. K.
Kwok, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, B. Z. Tang, Angew.
Chem., Int. Ed. 2018, 57, 5011−5015; c) Y. Tu, J. Liu, H. Zhang, Q. Peng,
J. W. Y. Lam, B. Z. Tang, Angew. Chem., Int. Ed. 2019, 58, 14911−14914;
d) H. Zhang, X. Zheng, N. Xie, Z. He, J. Liu, N. L. C. Leung, Y. Niu, X.
Huang, K. S. Wong, R. T. K. Kwok, H. H. Y. Sung, I. D. Williams, A. Qin, J.
W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2017, 139, 16264−16272.
[5] a) J.-S. Ni, P. Zhang, T. Jiang, Y. Chen, H. Su, D. Wang, Z.-Q. Yu, R. T. K.
Kwok, Z. Zhao, J. W. Y. Lam, B. Z. Tang, Adv. Mater. 2018, 30, 1805220;
b) J. Qi, C. Sun, A. Zebibula, H. Zhang, R. T. K. Kwok, X. Zhao, W. Xi, J.
W. Y. Lam, J. Qian, B. Z. Tang, Adv. Mater. 2018, 30, 1706856; c) S. Gao,
G. Wei, S. Zhang, B. Zheng, J. Xu, G. Chen, M. Li, S. Song, W. Fu, Z.
Xiao, W. Lu, Nat. Commun. 2019, 10, 2206.
[6] a) J. Wang, X. Gu, P. Zhang, X. Huang, X. Zheng, M. Chen, H. Feng, R. T.
K. Kwok, J. W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2017, 139,
16974−16979; b) J. Wang, X. Gu, H. Ma, Q. Peng, X. Huang, X. Zheng, S.
H. P. Sung, G. Shan, J. W. Y. Lam, Z. Shuai, B. Z. Tang, Nat. Commun.
2018, 9, 2963.
[7] a) J. S. Ni, M. M. S. Lee, P. Zhang, C. Gui, Y. Chen, D. Wang, Z. Q. Yu, R.
T. K. Kwok, J. W. Y. Lam, B. Z. Tang, Anal. Chem. 2019, 91, 2169−2176;
b) K. Wu, T. Zhang, Z. Wang, L. Wang, L. Zhan, S. Gong, C. Zhong, Z. H.
Lu, S. Zhang, C. Yang, J. Am. Chem. Soc. 2018, 140, 8877−8886; c) P.
Kaewmati, Y. Yakiyama, H. Ohtsu, M. Kawano, S. Haesuwannakij, S.
Higashibayashi, H. Sakurai, Mater. Chem. Front. 2018, 2, 514−519; d) L.
Peng, S. Xu, X. Zheng, X. Cheng, R. Zhang, J. Liu, B. Liu, A. Tong, Anal.
Chem. 2017, 89, 3162−3168.
F-AB-DMA in THF solution due to its weaker ICT and stronger
ESDBR. Resulting from fluorine substitution, intermolecular H-
bond is strengthened to further restrict the intramolecular
motions including ESDBR in the aggregation and solid states.
As a result, the solid-state luminescence and AIE performance
are dramatically enhanced. Interestingly, by accident of the
different E/Z-configurational stacking behaviors, only DMA-AB-F
has a suitable driving force to facilitate ISC from S1 to T1 states
to produce ROS in the aggregated state. As a result, DMA-AB-F
can serve as a photosensitizer for PDT to successfully eliminate
MDR bacteria both in vitro and in vivo. Noteworthy is that we
demonstrate a new strategy to design highly emissive AIEgens
using H-bonding restricted ESDBR property, which offers an
alternative approach to the design principle of traditional
AIEgens by introducing bulky rotor-substituents. This
investigative elucidation will not only break the structural limit for
typical AIEgen design, but also assist to expand new planar
AIEgens with novel properties for advanced biomedical
applications.
[8] J.-S. Ni, H. Liu, J. Liu, M. Jiang, Z. Zhao, Y. Chen, R. T. K. Kwok, J. W. Y.
Lam, Q. Peng, B. Z. Tang, Mater. Chem. Front. 2018, 2, 1498−1507.
[9] a) L. Yang, P. Ye, W. Li, W. Zhang, Q. Guan, C. Ye, T. Dong, X. Wu, W.
Zhao, X. Gu, Q. Peng, B. Tang, H. Huang, Adv. Opt. Mater. 2018, 6,
1701394; b) Y.-X. Yuan, B.-X. Wu, J.-B. Xiong, H.-C. Zhang, M. Hu, Y.-S.
Zheng, Dyes Pigm. 2019, 170, 107556.
[10] a) D. Dang, H. Liu, J. Wang, M. Chen, Y. Liu, H. H. Y. Sung, I. D. Williams,
R. T. K. Kwok, J. W. Y. Lam, B. Z. Tang, Chem. Mater. 2018, 30,
7892−7901; b) M. Gon, K. Tanaka, Y. Chujo, Angew. Chem., Int. Ed. 2018,
57, 6546−6551.
Experimental Section
The experimental details were described in the supporting
information.
[11] M. Yamaguchi, S. Ito, A. Hirose, K. Tanaka, Y. Chujo, Mater. Chem. Front.
2017, 1, 1573−1579.
Acknowledgements
[12] a) S. Xu, Y. Yuan, X. Cai, C. J. Zhang, F. Hu, J. Liang, G. Zhang, D.
Zhang, B. Liu, Chem. Sci. 2015, 6, 5824−5830; b) Z. Liu, H. Zou, Z. Zhao,
P. Zhang, G. G. Shan, R. T. K. Kwok, J. W. Y. Lam, L. Zheng, B. Z. Tang,
ACS Nano 2019, 13, 11283−11293; c) L. Yang, X. Wang, G. Zhang, X.
Chen, G. Zhang, J. Jiang, Nanoscale 2016, 8, 17422−17426.
[13] X. Wei, M. J. Zhu, Z. Cheng, M. Lee, H. Yan, C. Lu, J. J. Xu, Angew.
Chem., Int. Ed. 2019, 58, 3162−3166.
[14] a) H. Wu, Y. Pan, J. Zeng, L. Du, W. Luo, H. Zhang, K. Xue, P. Chen, D. L.
Phillips, Z. Wang, A. Qin, B. Z. Tang, Adv. Opt. Mater. 2019, 7, 1900283;
b) H. Zhang, Y. Nie, J. Miao, D. Zhang, Y. Li, G. Liu, G. Sun, X. Jiang, J.
Mater. Chem. C 2019, 7, 3306−3314.
The authors are grateful to the National Natural Science
Foundation of China (31870991), the Thousand Young Talents
Program, and the Science and Technology Plan of Shenzhen
(JCYJ20180306174918294) for financial support. The authors
also acknowledge the Center for Computational Science and
Engineering at SUSTech for theoretical calculation support and
SUSTech Core Research Facilities for technical support. All in
vivo procedures have been approved by the Animal Ethics
Committee of the Center for Experimental Animal Research of
SUSTech, China.
[15] T. Zhang, Q. Peng, C. Quan, H. Nie, Y. Niu, Y. Xie, Z. Zhao, B. Z. Tang, Z.
Shuai, Chem. Sci. 2016, 7, 5573−5580.
[16] C. Yu, Z. Huang, W. Gu, Q. Wu, E. Hao, Y. Xiao, L. Jiao, W.-Y. Wong,
Mater. Chem. Front. 2019, 3, 1823−1832.
[17] a) J. Zhang, E. Sharman, L. Yang, J. Jiang, G. Zhang, J. Phys. Chem. C
2018, 122, 25796−25803; b) J. Xu, X. Zhu, J. Guo, J. Fan, J. Zeng, S.
Chen, Z. Zhao, B. Z. Tang, ACS Mater. Lett. 2019, 1, 613−619.
[18] W. Wu, D. Mao, S. Xu, Kenry, F. Hu, X. Li, D. Kong, B. Liu, Chem 2018, 4,
1937−1951.
Keywords: aggregation-induced emission • organoboron •
photodynamic therapy • H-bond • conical intersection
[19] a) A. P. Magiorakos, A. Srinivasan, R. B. Carey, Y. Carmeli, M. E. Falagas,
C. G. Giske, S. Harbarth, J. F. Hindler, G. Kahlmeter, B. Olsson-Liljequist,
D. L. Paterson, L. B. Rice, J. Stelling, M. J. Struelens, A. Vatopoulos, J. T.
Weber, D. L. Monnet, Clin. Microbiol. Infect. 2012, 18, 268−281; b) L.
Dijkshoorn, A. Nemec, H. Seifert, Nat. Rev. Microbiol. 2007, 5, 939−951;
c) K. M. O'Connell, J. T. Hodgkinson, H. F. Sore, M. Welch, G. P. Salmond,
D. R. Spring, Angew. Chem., Int. Ed. 2013, 52, 10706−10733.
[20] a) X. Liu, M. Li, T. Han, B. Cao, Z. Qiu, Y. Li, Q. Li, Y. Hu, Z. Liu, J. W. Y.
Lam, X. Hu, B. Z. Tang, J. Am. Chem. Soc. 2019, 141, 11259−11268; b) B.
Wang, G. Feng, M. Seifrid, M. Wang, B. Liu, G. C. Bazan, Angew. Chem.,
Int. Ed. 2017, 56, 16063−16066; c) M. Wu, W. Wu, Y. Duan, X. Li, G. Qi,
B. Liu, Chem. Mater. 2019, 31, 7212−7220; d) D. Cui, J. Huang, X. Zhen,
J. Li, Y. Jiang, K. Pu, Angew. Chem., Int. Ed. 2019, 58, 5920−5924.
[21] a) M. Jiang, X. Gu, R. T. K. Kwok, Y. Li, H. H. Y. Sung, X. Zheng, Y. Zhang,
J. W. Y. Lam, I. D. Williams, X. Huang, K. S. Wong, B. Z. Tang, Adv. Funct.
Mater. 2018, 28, 1704589; b) E. Zhao, Y. Chen, S. Chen, H. Deng, C. Gui,
C. W. Leung, Y. Hong, J. W. Lam, B. Z. Tang, Adv. Mater. 2015, 27,
4931−4937.
[1] a) D. Ding, D. Mao, K. Li, X. Wang, W. Qin, R. Liu, D. S. Chiam, N.
Tomczak, Z. Yang, B. Z. Tang, D. Kong, B. Liu, ACS Nano 2014, 8,
12620−12631; b) H. Gao, X. Zhang, C. Chen, K. Li, D. Ding, Adv. Biosyst.
2018, 2, 1800074; c) H. Liu, J. Zeng, J. Guo, H. Nie, Z. Zhao, B. Z. Tang,
Angew. Chem., Int. Ed. 2018, 57, 9290−9294; d) J.-S. Ni, Y. Li, W. Yue, B.
Liu, K. Li, Theranostics 2020, 10, 1923−1947.
[2] a) J. Qi, C. Chen, D. Ding, B. Z. Tang, Adv. Healthc. Mater. 2018, 7,
1800477; b) J. Mei, N. L. C. Leung, R. T. K. Kwok, J. W. Y. Lam, B. Z.
Tang, Chem. Rev. 2015, 115, 11718−11940; c) G. Feng, B. Liu, Acc.
Chem. Res. 2018, 51, 1404−1414.
[3] a) G. Chen, W. Li, T. Zhou, Q. Peng, D. Zhai, H. Li, W. Z. Yuan, Y. Zhang,
B. Z. Tang, Adv. Mater. 2015, 27, 4496−4501; b) F. Ren, J. Shi, B. Tong, Z.
Cai, Y. Dong, Mater. Chem. Front. 2019, 3, 2072−2076; c) H. Lu, Y.
Zheng, X. Zhao, L. Wang, S. Ma, X. Han, B. Xu, W. Tian, H. Gao, Angew.
Chem., Int. Ed. 2016, 55, 155–159; d) M. M. Islam, Z. Hu, Q. Wang, C.
Redshaw, X. Feng, Mater. Chem. Front. 2019, 3, 762−781; e) W. Li, Y.
Ding, M. Tebyetekerwa, Y. Xie, L. Wang, H. Li, R. Hu, Z. Wang, A. Qin, B.
Z. Tang, Mater. Chem. Front. 2019, 3, 2491−2498; f) W. Yao, M.
Tebyetekerwa, X. Bian, W. Li, S. Yang, M. Zhu, R. Hu, Z. Wang, A. Qin, B.
Z. Tang, J. Mater. Chem. C 2018, 6, 12849−12857.
[22] C. H. Lo, S. Akbarzadeh, C. McLean, A. Ives, E. Paul, W. A. Brown, H.
Cleland, J. Plast. Reconstr. Aes. 2019, 72, 427−437.
[23] M. Zhao, M. Yang, E. Baranov, X. Wang, S. Penman, A. R. Moossa, R. M.
Hoffman, Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 9814−9818.
This article is protected by copyright. All rights reserved.