Citation: Luo Weijian, Zhang Yiren, Gong Yongyang, Zhou Qing, Zhang Yongming, Yuan Wangzhang. Crystallization-induced phosphorescence, remarkable mechanochromism, and grinding enhanced emission of benzophenone-aromatic amine conjugates[J]. Chinese Chemical Letters, ;2018, 29(10): 1533-1536. doi: 10.1016/j.cclet.2018.08.001 shu

Crystallization-induced phosphorescence, remarkable mechanochromism, and grinding enhanced emission of benzophenone-aromatic amine conjugates

Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Electrochemical Energy Devices Research Center, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Yuan Wangzhang, wzhyuan@sjtu.edu.cn
Received Date: 13 June 2018
Revised Date: 31 July 2018
Accepted Date: 1 August 2018
Available Online: 4 October 2018

Figures(4)

Pure organic luminogens with efficient room temperature phosphorescence (RTP) and remarkable mechanochromism are highly desired in view of their fundamental significance and technical applications. Herein, four twisted pure organic luminogens based on benzophenone and aromatic amines were synthesized and their photophysical properties were thoroughly investigated. They exhibit crystallization-induced phosphorescence (CIP), giving bright fluorescence and phosphorescence dual emission in crystals. Upon grinding, they become amorphous and emit predominantly red-shifted fluorescence, demonstrating remarkable mechanochromism. Furthermore, three of them even demonstrate greatly enhanced emission upon grinding, which is rarely observed in twisted D-A structured luminogens.
- Crystallization-induced phosphorescence,
- Room temperature phosphorescence,
- Mechanochromism,
- Benzophenone,
- Aromatic amines
1. [1]
  Y. Ma, H. Zhang, J. Shen, C. Che, Synth. Met. 94(1998) 245-248. doi: 10.1016/S0379-6779(97)04166-0
2. [2]
  K. Li, L. Zhao, Y. Gong, W.Z. Yuan, Y. Zhang, Sci. China Chem. 60(2017) 806-812. doi: 10.1007/s11426-016-0460-8
3. [3]
  X. Dou, Q. Zhou, X. Chen, et al., Biomacromolecules 19(2018) 2014-2022. doi: 10.1021/acs.biomac.8b00123
4. [4]
  Y. Yang, K.Z. Wang, D. Yan, ACS Appl. Mater. Interfaces 9(2017) 17399-17407. doi: 10.1021/acsami.7b00594
5. [5]
  H. Sun, S. Liu, W. Lin, et al., Nat. Commun. 5(2014) 3601-3609. doi: 10.1038/ncomms4601
6. [6]
  D. Li, F. Lu, J. Wang, et al., J. Am. Chem. Soc. 140(2018) 1916-1923. doi: 10.1021/jacs.7b12800
7. [7]
  X. Zhou, H. Liang, P. Jiang, et al., Adv. Sci. 3(2016)1500155. doi: 10.1002/advs.201500155
8. [8]
  I.J. MacDonald, T.J. Dougherty, J. Porphyrins Phthalocyanines 5(2001) 105-129. doi: 10.1002/jpp.328
9. [9]
  F. Clabau, X. Rocquefelte, T. Le Mercier, et al., Chem. Mater. 18(2006) 3212-3220. doi: 10.1021/cm052728q
10. [10]
  Y.C. Zhu, L. Zhou, H.Y. Li, et al., Adv. Mater. 23(2011) 4041-4046. doi: 10.1002/adma.v23.35
11. [11]
  G. Zhou, C.L. Ho, W.Y. Wong, et al., Adv. Funct. Mater. 18(2008) 499-511. doi: 10.1002/(ISSN)1616-3028
12. [12]
  J. Ding, J. Lu, Y. Cheng, et al., Adv. Funct. Mater. 18(2008) 2754-2762. doi: 10.1002/adfm.v18:18
13. [13]
  Y. Zhu, C. Gu, S. Tang, et al., J. Mater. Chem. 19(2009) 3941-3949. doi: 10.1039/b900481e
14. [14]
  M.C. Tang, C.H. Lee, S.L. Lai, et al., J. Am. Chem. Soc. 139(2017) 9341-9349. doi: 10.1021/jacs.7b04788
15. [15]
  N.J. Turro, V. Ramamurthy, J.C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, 2009.
16. [16]
  J.B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, London, 1970.
17. [17]
  W.Z. Yuan, X.Y. Shen, H. Zhao, et al., J. Phys. Chem. C 114(2010) 6090-6099. doi: 10.1021/jp909388y
18. [18]
  C.R. Wang, Y.Y. Gong, W.Z. Yuan, Y.M. Zhang, Chin. Chem. Lett. 27(2016) 1184-1192. doi: 10.1016/j.cclet.2016.05.026
19. [19]
  S. Hirata, Adv. Opt. Mater. 5(2017)1700116.
20. [20]
  S. Xu, R. Chen, C. Zheng, W. Huang, Adv. Mater. 28(2016) 9920-9940. doi: 10.1002/adma.201602604
21. [21]
  E.B. Asafu-Adjaye, S.Y. Su, Anal. Chem. 58(1986) 539-543. doi: 10.1021/ac00294a009
22. [22]
  Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27(2015) 6195-6201. doi: 10.1002/adma.201502442
23. [23]
  Z. He, W. Zhao, J.W.Y. Lam, et al., Nat. Commun. 8(2017) 416. doi: 10.1038/s41467-017-00362-5
24. [24]
  J. Yang, X. Zhen, B. Wang, et al., Nat. Commun. 9(2018) 840. doi: 10.1038/s41467-018-03236-6
25. [25]
  Z. An, C. Zheng, Y. Tao, et al., Nat. Mater. 14(2015) 685-690. doi: 10.1038/nmat4259
26. [26]
  S.M.A. Fateminia, Z. Mao, S. Xu, et al., Angew. Chem. Int. Ed. 56(2017) 12160-12164. doi: 10.1002/anie.201705945
27. [27]
  Z. Mao, Z. Yang, Y. Mu, et al., Angew. Chem. Int. Ed. 54(2015) 6270-6273. doi: 10.1002/anie.201500426
28. [28]
  C. Zhou, T. Xie, R. Zhou, et al., ACS Appl. Mater. Interfaces 7(2015) 17209-17216. doi: 10.1021/acsami.5b04075
29. [29]
  G. Yong, X. Zhang, W. She, Dyes Pigments 97(2013) 65-70. doi: 10.1016/j.dyepig.2012.11.026
30. [30]
  X. Yang, D. Yan, Chem. Sci. 7(2016) 4519-4526. doi: 10.1039/C6SC00563B
31. [31]
  X. Yang, D. Yan, Adv. Opt. Mater. 4(2016) 897-905. doi: 10.1002/adom.v4.6
32. [32]
  Z. Chi, X. Zhang, B. Xu, et al., Chem. Soc. Rev. 41(2012) 3878-3896. doi: 10.1039/c2cs35016e
33. [33]
  W.B. Li, W.J. Luo, K.X. Li, W.Z. Yuan, Y.M. Zhang, Chin. Chem. Lett. 28(2017) 1300-1305. doi: 10.1016/j.cclet.2017.04.008
34. [34]
  C.Y. Li, X. Tang, L.Q. Zhang, et al., Adv. Opt. Mater. 3(2015) 1184-1190. doi: 10.1002/adom.v3.9
35. [35]
  J. Mei, J. Wang, A.J. Qin, et al., J. Mater. Chem. 22(2012) 4290-4298. doi: 10.1039/C1JM12673C
36. [36]
  C.D. Dou, D. Chen, J. Iqbal, et al., Langmuir 27(2011) 6323-6329. doi: 10.1021/la200382b
37. [37]
  Z. Ma, Z. Wang, X. Meng, et al., Angew. Chem. Int. Ed. 55(2016) 519-522. doi: 10.1002/anie.201507197
38. [38]
  Y. Dong, B. Xu, J. Zhang, et al., Angew. Chem. Int. Ed. 51(2012) 10782-10785. doi: 10.1002/anie.v51.43
39. [39]
  Y. Wang, Z. He, G. Chen, et al., Chin. Chem. Lett. 28(2017) 2133-2138. doi: 10.1016/j.cclet.2017.09.054
40. [40]
  S. Sarkar, H.P. Hendrickson, D. Lee, et al., J. Phys. Chem. C 121(2017) 3771-3777. doi: 10.1021/acs.jpcc.6b12027
41. [41]
  W.Z. Yuan, Y. Tan, Y. Gong, et al., Adv. Mater. 25(2013) 2837-2843. doi: 10.1002/adma.201205043
42. [42]
  Y. Gong, Y. Tan, J. Liu, et al., Chem. Commun. 49(2013) 4009-4011. doi: 10.1039/c3cc39243k
43. [43]
  Y. Zhang, J. Sun, G. Zhang, et al., J. Mater. Chem. C 2(2014) 195-200. doi: 10.1039/C3TC31416B
44. [44]
  S. Reineke, M.A. Baldo, Sci. Rep. 4(2014) 3797-3804.
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