Citation: Duan Yuxin, Xiang Xueqin, Dong Yongqiang. Diphenyldibenzofulvene Derivatives Exhibiting Reversible Multicolored Mechanochromic Luminescence with High Contrast[J]. Acta Chimica Sinica, ;2016, 74(11): 923-928. doi: 10.6023/A16080433 shu

Diphenyldibenzofulvene Derivatives Exhibiting Reversible Multicolored Mechanochromic Luminescence with High Contrast

1.
Beijing Key Laboratory of Energy Conversion and Storage Materials, Department of Chemistry, Beijing Normal University, Beijing 100875

Corresponding author: Dong Yongqiang, dongyq@bnu.edu.cn
Received Date: 25 August 2016

Fund Project: National Natural Science Foundation of China 51173018

Figures(6)

High performance mechanochromic luminescent (MCL) materials exhibiting multicolored emission switching or high contrast emission color and efficiency have seldom been reported despite their potential application to improve the complexity of anti-fake or increase the density of optical data storage. Through combination of the large conjugation core and peripheral phenyl rings, we designed and synthesized phenyltolyldibenzofulvene (1). Luminogen 1 exhibits aggregation induced emission (AIE) and crystallization enhanced emission (CEE). Luminogen 1 can form blue (1CB, 465 nm, Φ=14.6%) and blue-green (1CA, 485 nm, Φ=13.9%) emissive crystals through slow solvent evaporation of chloroform/hexane and 1, 2-dichlorethane/hexane, respectively, and its amorphous solid (1Am, 525 nm, Φ=2.1%) emits dark yellow green light. The propeller-like conformation of 1 affords loose packing pattern and facilitates the morphology tuning in the solid state. Thus, emission of 1 can be switched reversibly among blue, blue-green and yellow-green through modulation of morphology by mechanical stimuli, heating or solvent fuming. Moreover, the mechanochromic luminescence of 1 affords its potential application in optical recording. Ground powder of 1 was dispersed on weighing paper, and a yellow-green emissive paper was obtained. The paper can be transformed to blue and blue-green emissive through solvent fuming, and dark green letters on the blue and blue-green emissive paper could be obtained through writing with glass rod due to the amorphization of luminogen 1 in the written area. The letters can be erased through solvent fuming, heating or grinding, so the paper can be switched to blue, blue-green, or yellow-green emissive depending on the erasing method. Thus, following the strategy of combination of the large conjugation core and peripheral phenyl rings, the obtained luminogen exhibit multicolored MCL emission switching with high contrast. And the molecular design strategy for high performance MCL materials was further verified.
- AIE,
- crystallization enhanced emission,
- propeller-like conformation,
- high performance mechanochromic luminescence,
- optical recording
1. [1]
  Sagara, Y.; Kato, T. Nat. Chem. 2009, 1, 605; (b) Chi, Z.; Zhang, X.; Xu, B.; Zhou, X.; Ma, C.; Zhang, Y.; Liu, S.; Xu, J. Chem. Soc. Rev. 2012, 41, 3878; (c) Dong, Y. Q.; Lam, J. W. Y.; Tang, B. Z. J. Phys. Chem. Lett. 2015, 6, 3429; (d) Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718; (e) Qian, X.; Su, M.; Li, F. Y.; Song, Y. L. Acta Chim. Sinica 2016, 74, 565. (钱鑫, 苏萌, 李风煜, 宋延林, 化学学报, 2016, 74, 565.)
2. [2]
  Hu, T.; Yao, B.; Chen, X.; Li, W.; Song, Z.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Commun. 2015, 51, 8849; (b) Wang, L.; Wang, K.; Zou, B.; Ye, K.; Zhang, H.; Wang, Y. Adv. Mater. 2015, 27, 2918; (c) Sun, M.; Zhang, D.; Li, Y.; Wang, J.; Gao, Y.; Yang, W. J. Lumin. 2014, 148, 55; (d) Zheng, M.; Zhang, D. T.; Sun, M. X.; Li, Y. P.; Liu, T. L.; Xue, S. F.; Yang, W. J. J. Mater. Chem. C 2014, 2, 1913; (e) Botta, C.; Benedini, S.; Carlucci, L.; Forni, A.; Marinotto, D.; Nitti, A.; Pasini, D.; Righetto, S.; Cariati, E. J. Mater. Chem. C 2016, 4, 2979.
3. [3]
  Tong, J.; Wang, Y. J.; Wang, Z.; Sun, J. Z.; Tang, B. Z. J. Phys. Chem. C 2015, 119, 21875; (b) Mei, J.; Hong, Y. N.; Lam, J. W. Y.; Qin, A. J.; Tang, Y. H.; Tang, B. Z. Adv. Mater. 2014, 26, 5429; (c) Dong, Y. Q.; Lam, J. W. Y.; Li, Z.; Qin, A. J.; Tong, H.; Dong, Y. P.; Feng, X. D.; Tang, B. Z. J. Inorg. Organomet. Polym. Mater. 2005, 15, 287; (d) Luo, J. D.; Xie, Z. L.; Lam, J. W. Y.; Cheng, L.; Chen, H. Y.; Qiu, C. F.; Kwok, H. S.; Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B. Z. Chem. Commun. 2001, 1740; (e) He, Z.; Zhang, L.; Mei, J.; Zhang, T.; Lam, J. W. Y.; Shuai, Z.; Dong, Y. Q.; Tang, B. Z. Chem. Mater. 2015, 27, 6601; (f) Wang, C.; Xu, B. J.; Li, M. S.; Chi, Z. G.; Xie, Y. J.; Li, Q. Q.; Li, Z. Mater. Horiz. 2016, 3, 220; (g) Xia, Z. Q.; Shao, A. D.; Li, Q.; Zhu, S. Q.; Zhu, W. H. Acta Chim. Sinica 2016, 74, 351. (夏志清, 邵安东, 李强, 朱世琴, 朱为宏, 化学学报, 2016, 74, 351.); (h) Xun, Z. Q.; Tang, H. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Zhang, X. H.; Li, Y. Acta Chim. Sinica 2015, 73, 819. (寻知庆, 唐海云, 曾毅, 陈金平, 于天君, 张小辉, 李嫕, 化学学报, 2015, 73, 819.); (i) Tong, H.; Dong, Y. Q.; Hong, Y. N.; Haussler, M.; Lam, J. W. Y.; Sung, H. H. Y.; Yu, X. M.; Sun, J. X.; Williams, I. D.; Kwok, H. S.; Tang, B. Z. J. Phys. Chem. C 2007, 111, 2287.
4. [4]
  Yuan, W. Z.; Tan, Y.; Gong, Y.; Lu, P.; Lam, J. W. Y.; Shen, X. Y.; Feng, C.; Sung, H. H. Y.; Lu, Y.; Williams, I. D.; Sun, J. Z.; Zhang, Y.; Tang, B. Z. Adv. Mater. 2013, 25, 2837; (b) Mao, W. G.; Chen, K.; Ouyang, M.; Sun, J. W.; Zhou, Y. B.; Wang, Y. S.; Song, Q. B.; Zhang, C. Chin. J. Org. Chem. 2014, 34, 161. (毛文纲, 陈康, 欧阳密, 孙璟玮, 周永兵, 王永胜, 宋庆宝, 张诚, 有机化学, 2014, 34, 161.)
5. [5]
  Ma, Z.; Teng, M.; Wang, Z.; Yang, S.; Jia, X. Angew. Chem. Int. Ed. 2013, 125, 12494; (b) Ma, Z.; Wang, Z.; Teng, M.; Xu, Z.; Jia, X. ChemPhysChem 2015, 16, 1811; (c) He, B. R.; Chang, Z. F.; Jiang, Y. B.; Xu, X. F.; Lu, P.; Kwok, H. S.; Zhou, J.; Qiu, H. Y.; Zhao, Z. J.; Tang, B. Z. Dyes Pigm. 2014, 106, 87; (d) Dong, Y. J.; Zhang, J. B.; Tan, X.; Wang, L. J.; Chen, J. L.; Li, B.; Ye, L.; Xu, B.; Zou, B.; Tian, W. J. J. Mater. Chem. C 2013, 1, 7554.
6. [6]
  Ma, Z.; Wang, Z.; Meng, X.; Ma, Z.; Xu, Z.; Ma, Y.; Jia, X. Angew. Chem., Int. Ed. 2016, 55, 519; (b) Sagara, Y.; Kato, T. Angew. Chem., Int. Ed. 2011, 50, 9128; (c) Xue, P.; Ding, J.; Wang, P.; Lu, R. J. Mater. Chem. C 2016, 4, 6688.
7. [7]
  Zhao, Z.; Chen, T.; Jiang, S.; Liu, Z.; Fang, D.; Dong, Y. Q. J. Mater. Chem. C 2016, 4, 4800; (b) Luo, X. L.; Li, J. N.; Li, C. H.; Heng, L. P.; Dong, Y. Q.; Liu, Z. P.; Bo, Z. S.; Tang, B. Z. Adv. Mater. 2011, 23, 3261; (c) Li, C.; Luo, X.; Zhao, W.; Huang, Z.; Liu, Z.; Tong, B.; Dong, Y. Sci. China Chem. 2013, 56, 1173.
8. [8]
  Dong, Y. Q.; Lam, J. W. Y.; Qin, A.; Sun, J. X.; Liu, J. Z.; Li, Z.; Sun, J. Z.; Sung, H. H. Y.; Williams, I. D.; Kwok, H. S.; Tang, B. Z. Chem. Commun. 2007, 3255; (b) Dong, Y. Q.; Lam, J. W. Y.; Qin, A. J.; Li, Z.; Sun, J. Z.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z. Chem. Commun. 2007, 40.
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沈阳化工大学材料科学与工程学院沈阳 110142