Multi-Stimuli-Induced Mechanical Bending and Reversible Fluorescence Switching in a Single Organic Crystal
Corresponding Author
Prof. Dr. Xin Zheng
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorXiaojing Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorLijie Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorDr. Xiaochuan Li
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorSong Jiang
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorCaoyuan Niu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorPuhui Xie
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorGuoxing Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorZhanqi Cao
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorYunlai Ren
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorYuchen Qin
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorProf. Dr. Jianji Wang
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xin Zheng
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorXiaojing Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorLijie Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorDr. Xiaochuan Li
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorSong Jiang
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorCaoyuan Niu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorPuhui Xie
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorGuoxing Liu
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorZhanqi Cao
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorYunlai Ren
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorYuchen Qin
College of Science, Henan Agricultural University, Zhengzhou, 450002 P. R. China
Search for more papers by this authorProf. Dr. Jianji Wang
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorAbstract
Fluorescent single crystals that respond to multiple external stimuli are of great interest in molecular machines, sensors, and displays. The integration of photo- or acid-induced fluorescence enhancement and bending in one organic crystal, however, has not been reported yet. Herein, we report the interesting plastic photomechanical bending and switching on of the fluorescence of an azine crystal in a single-crystal transformation, due to extended π-conjugation and molecular slippage. Moreover, the fluorescent plastic bending driven by multiple volatile acid vapors was firstly observed, and attributed to the synergistic effect of push–pull electronic structure and hydrogen bonding. The single crystal also shows high elasticity under external force. In addition, reversible fluorescence switching can be triggered by grinding and solvent fuming, as well as by the adsorption and desorption of HCl vapor. The integration of plastic, elastic bending and switch-on fluorescence into one single crystal provides a new strategy for next-generation smart materials.
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References
- 1N. Huebsch, D. J. Mooney, Nature 2009, 462, 426–432.
- 2
- 2aO. S. Bushuyev, A. Tomberg, T. Friščić, C. J. Barrett, J. Am. Chem. Soc. 2013, 135, 12556–12559;
- 2bR. Samanta, S. Ghosh, R. Devarapalli, C. M. Reddy, Chem. Mater. 2018, 30, 577–581;
- 2cY. Sun, Y. Lei, H. Dong, Y. Zhen, W. Hu, J. Am. Chem. Soc. 2018, 140, 6186–6189.
- 3
- 3aL. Zhu, R. O. Al-Kaysi, C. J. Bardeen, J. Am. Chem. Soc. 2011, 133, 12569–12575;
- 3bD. Kitagawa, H. Nishi, S. Kobatake, Angew. Chem. Int. Ed. 2013, 52, 9320–9322; Angew. Chem. 2013, 125, 9490–9492;
- 3cP. Gupta, D. P. Karothu, E. Ahmed, P. Naumov, N. K. Nath, Angew. Chem. Int. Ed. 2018, 57, 8498–8502; Angew. Chem. 2018, 130, 8634–8638.
- 4J. Guo, J. Fan, X. Liu, Z. Zhao, B. Z. Tang, Angew. Chem. Int. Ed. 2020, 59, 8828–8832; Angew. Chem. 2020, 132, 8913–8917.
- 5
- 5aE. Uchida, R. Azumi, Y. Norikane, Nat. Commun. 2015, 6, 7310–7316;
- 5bT. Taniguchi, H. Sugiyama, H. Uekusa, M. Shiro, T. Asahi, H. Koshima, Nat. Commun. 2018, 9, 538.
- 6D. P. Karothu, J. Weston, I. T. Desta, P. Naumov, J. Am. Chem. Soc. 2016, 138, 13298–13306.
- 7
- 7aS. Hayashi, T. Koizumi, Angew. Chem. Int. Ed. 2016, 55, 2701–2704; Angew. Chem. 2016, 128, 2751–2754;
- 7bA. K. Saini, K. Natarajan, S. M. Mobin, Chem. Commun. 2017, 53, 9870–9873;
- 7cE. P. Kenny, A. C. Jacko, B. J. Powell, Angew. Chem. Int. Ed. 2019, 58, 15082–15088; Angew. Chem. 2019, 131, 15226–15232.
- 8
- 8aX. Yan, F. Wang, B. Zheng, F. Huang, Chem. Soc. Rev. 2012, 41, 6042–6065;
- 8bZ. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liu, J. Xu, Chem. Soc. Rev. 2012, 41, 3878–3896;
- 8cP. Wei, J. X. Zhang, Z. Zhao, Y. Chen, X. He, M. Chen, J. Gong, H. H. Sung, I. D. Williams, J. W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2018, 140, 1966–1975.
- 9
- 9aM. K. Panda, S. Ghosh, N. Yasuda, T. Moriwaki, G. D. Mukherjee, C. M. Reddy, P. Naumov, Nat. Chem. 2015, 7, 65–72;
- 9bJ. M. Halabi, M. B. Al-Handawi, L. Li, J. Am. Chem. Soc. 2020, 142, 13256–13272.
- 10Y. Huang, J. Xing, Q. Gong, L.-C. Chen, G. Liu, C. Yao, Z. Wang, H.-L. Zhang, Z. Chen, Q. Zhang, Nat. Commun. 2019, 10, 169.
- 11
- 11aS. Park, O. Kwon, S. Kim, S. Park, M. G. Choi, M. Cha, S. Y. Park, D. J. Jang, J. Am. Chem. Soc. 2005, 127, 10070–10074;
- 11bZ. Zhang, B. Xu, J. Su, L. Shen, Y. Xie, H. Tian, Angew. Chem. Int. Ed. 2011, 50, 11654–11657; Angew. Chem. 2011, 123, 11858–11861;
- 11cS. Saha, M. K. Mishra, C. M. Reddy, G. R. Desiraju, Acc. Chem. Res. 2018, 51, 2957–2967.
- 12
- 12aS. Ghosh, M. K. Mishra, S. Ganguly, G. R. Desiraju, J. Am. Chem. Soc. 2015, 137, 9912–9921;
- 12bS. Hayashi, S. Y. Yamamoto, D. Takeuchi, Y. Ie, K. Takagi, Angew. Chem. Int. Ed. 2018, 57, 17002–17008; Angew. Chem. 2018, 130, 17248–17254;
- 12cE. Ahmed, D. P. Karothu, M. Warren, P. Naumov, Nat. Commun. 2019, 10, 3723;
- 12dT. Takeda, M. Ozawa, T. Akutagawa, Angew. Chem. Int. Ed. 2019, 58, 10345–10352; Angew. Chem. 2019, 131, 10453–10460;
- 12eM. Annadhasan, A. R. Agrawal, S. Bhunia, V. V. Pradeep, S. S. Zade, C. M. Reddy, R. Chandrasekar, Angew. Chem. Int. Ed. 2020, 59, 13852–13858; Angew. Chem. 2020, 132, 13956–13962.
- 13
- 13aH. P. Liu, Z. Q. Lu, Z. L. Zhang, Y. Wang, H. Y. Zhang, Angew. Chem. Int. Ed. 2018, 57, 8448–8452; Angew. Chem. 2018, 130, 8584–8588;
- 13bR. Huang, C. G. Wang, Y. Wang, H. Y. Zhang, Adv. Mater. 2018, 30, 1800814; H. Liu, K. Ye, Z. L. Zhang, H. Y. Zhang, Angew. Chem. Int. Ed. 2019, 58, 19081–19086; Angew. Chem. 2019, 131, 19257–19262;
- 13cZ. Lu, Y. Zhang, H. Liu, K. Ye, W. Liu, H. Zhang, Angew. Chem. Int. Ed. 2020, 59, 4299–4303; Angew. Chem. 2020, 132, 4329–4333.
- 14
- 14aB. Bhattacharya, D. Roy, S. Dey, A. Puthuvakkal, S. Bhunia, S. Mondal, R. Chowdhury, M. Bhattacharya, M. Mandal, K. Manoj, P. K. Mandal, C. M. Reddy, Angew. Chem. Int. Ed. 2020, 59, 19878–19883; Angew. Chem. 2020, 132, 20050–20055;
- 14bT. Seki, N. Hoshino, Y. Suzuki, S. Hayashi, CrystEngComm 2021, 23, 5686–5696.
- 15P. Y. Li, J. X. Wang, P. F. Li, L. M. Lai, M. Z. Yin, Mater. Chem. Front. 2021, 5, 1355–1363.
- 16M. Annadhasan, S. Basak, N. Chandrasekhar, R. Chandrasekar, Adv. Opt. Mater. 2020, 8, 2000959.
- 17
- 17aM. Irie, T. Fulcaminato, K. Matsuda, S. Kobatake, Chem. Rev. 2014, 114, 12174–12277;
- 17bD. Tian, X. Zheng, X. Li, X. Liu, J. Zhao, J. Wang, Chem. Eur. J. 2019, 25, 16519–16522;
- 17cB. Liu, Z. Lu, B. Tang, H. Liu, H. Liu, Z. Zhang, K. Ye, H. Zhang, Angew. Chem. Int. Ed. 2020, 59, 23117–23121; Angew. Chem. 2020, 132, 23317–23321.
- 18J. Mei, N. L. Leung, R. T. Kwok, J. W. Lam, B. Z. Tang, Chem. Rev. 2015, 115, 11718–11940.
- 19
- 19aY. Sagara, S. Yamane, M. Mitani, C. Weder, T. Kato, Adv. Mater. 2016, 28, 1073–1095;
- 19bH. Wu, W. Chi, G. Baryshnikov, B. Wu, Y. Gong, D. Zheng, X. Li, Y. Zhao, X. Liu, H. Agren, L. Zhu, Angew. Chem. Int. Ed. 2019, 58, 4328–4333; Angew. Chem. 2019, 131, 4372–4377.
- 20C. Yang, J. Yoon, S. H. Kim, K. Hong, D. S. Chung, K. Heo, C. E. Park, M. Ree, Appl. Phys. Lett. 2008, 92, 243305.
- 21
- 21aH. Qian, M. E. Cousins, E. H. Horak, A. Wakefield, M. D. Liptak, I. Aprahamian, Nat. Chem. 2017, 9, 83–87;
- 21bS. Ludwanowski, A. Samanta, S. Loescher, C. Barner-Kowollik, A. Walther, Adv. Sci. 2021, 8, 2003740.
- 22
- 22aW. Zhao, Z. He, Q. Peng, J. W. Y. Lam, H. Ma, Z. Qiu, Y. Chen, Z. Zhao, Z. Shuai, Y. Dong, B. Z. Tang, Nat. Commun. 2018, 9, 3044;
- 22bP. Alam, N. L. C. Leung, Y. Cheng, H. Zhang, J. Liu, W. Wu, R. T. K. Kwok, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, B. Z. Tang, Angew. Chem. Int. Ed. 2019, 58, 4536–4540; Angew. Chem. 2019, 131, 4584–4588.
- 23
- 23aB. Liu, A. Pucci, Mater. Chem. Front. 2017, 1, 1689–1690;
- 23bJ.-A. Li, J. Zhou, Z. Mao, Z. Xie, Z. Yang, B. Xu, C. Liu, X. Chen, D. Ren, H. Pan, G. Shi, Y. Zhang, Z. Chi, Angew. Chem. Int. Ed. 2018, 57, 6449–6453; Angew. Chem. 2018, 130, 6559–6563;
- 23cY. Chen, C. Xu, B. Xu, Z. Mao, J.-A. Li, Z. Yang, N. R. Peethani, C. Liu, G. Shi, F. L. Gu, Y. Zhang, Z. Chi, Mater. Chem. Front. 2019, 3, 1800–1806.
- 24
- 24aX. Cheng, K. Wang, S. Huang, H. Y. Zhang, H. Y. Zhang, Y. Wang, Angew. Chem. Int. Ed. 2015, 54, 8369–8373; Angew. Chem. 2015, 127, 8489–8493;
- 24bJ. Calbo, C. E. Weston, A. J. P. White, H. S. Rzepa, J. Contreras-García, M. J. Fuchter, J. Am. Chem. Soc. 2017, 139, 1261–1274.
- 25Deposition Numbers 2110031, 2110032, 2110034, 2110035, 2110037, 2110039 and 2110040 contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.
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