Citation: Chen Weijie, Pan Yingle, Chen Jianhua, Ye Fengying, Liu Sheng Hua, Yin Jun. Stimuli-responsive organic chromic materials with near-infrared emission[J]. Chinese Chemical Letters, ;2018, 29(10): 1429-1435. doi: 10.1016/j.cclet.2018.08.011 shu

Stimuli-responsive organic chromic materials with near-infrared emission

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China

Corresponding author: Yin Jun, yinj@mail.ccnu.edu.cn
Received Date: 31 July 2018
Revised Date: 23 August 2018
Accepted Date: 23 August 2018
Available Online: 27 October 2018

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Organic chromic materials that respond to external stimuli, especially in the solid state, have sparked extensive interest owing to their potential use as smart materials. In particular, the availability of chromic materials, which emit fluorescence or phosphorescence in the deep penetrating, near-infrared (NIR) region, has led to great improvements in imaging. Various methods that were commonly applied to construct chromic materials, have been reformed to develop the novel type of compounds, and some have received rewards with excellent fingdings. Relevant research achievements of practical applications have showed their potential with the changes that locate in the NIR region, while further in-depth explorations about the inherent chromic chromism are underway. In this review, several representative studies, which have led the development of responsive organic chromic materials with near-infrared emission, will be discussed.
- Stimuli-response,
- Near-infrared emission,
- Fluorescent dyes,
- Chromic materials,
- Mechanochromism
1. [1]
  Y. Shiraishi, R. Miyamoto, T. Hirai, Org. Lett. 11(2009) 1571-1574. doi: 10.1021/ol900188m
2. [2]
  E.P. Chan, J.J. Walish, E.L. Thomas, C.M. Stafford, Adv. Mater. 23(2011) 4702-4706. doi: 10.1002/adma.201102662
3. [3]
  X.J. Xie, G. Mistlberger, E. Bakker, J. Am. Chem. Soc. 134(2012) 16929-16932. doi: 10.1021/ja307037z
4. [4]
  S.L. Wan, Y. Zheng, J. Shen, W.T. Yang, M. Yin, ACS Appl. Mater. Interfaces 6(2014) 19515-19519. doi: 10.1021/am506641t
5. [5]
  R.X. Zhang, P.F. Li, W.J. Zhang, N. Li, N. Zhao, J. Mater. Chem. C 4(2016) 10479-10485.
6. [6]
  K. Umezawa, D. Citterio, K. Suzuki, Anal. Sci. 30(2014) 1348-2246.
7. [7]
  Y. Ma, Y. Zeng, H. Liang, et al., J. Mater. Chem. C 3(2015) 11850-11856. doi: 10.1039/C5TC03327F
8. [8]
  T. Kowada, H. Maeda, K. Kikuchi, Chem. Soc. Rev. 44(2015) 4953-4972. doi: 10.1039/C5CS00030K
9. [9]
  H. Lu, Y. Zheng, X. Zhao, et al., Angew. Chem. Int. Ed. 55(2016) 155-159. doi: 10.1002/anie.201507031
10. [10]
  S. Leng, Q.L. Qiao, Y. Gao, et al., Chin. Chem. Lett. 28(2017) 1911-1915. doi: 10.1016/j.cclet.2017.03.034
11. [11]
  Z.Q. Xu, J.H. Chen, L.L. Hu, et al., Chin. Chem. Lett. 28(2017) 1935-1942. doi: 10.1016/j.cclet.2017.07.018
12. [12]
  Y.H. Chen, T.W. Wei, Z.J. Zhang, et al., Chin. Chem. Lett. 28(2017) 1957-1960. doi: 10.1016/j.cclet.2017.05.010
13. [13]
  H.B. Sun, S.J. Liu, W.P. Lin, et al., Nat. Commun. 5(2014) 3601-3609. doi: 10.1038/ncomms4601
14. [14]
  J.C.G. Bünzli, S.V. Eliseeva, Chem. Sci. 4(2013) 1939-1949. doi: 10.1039/c3sc22126a
15. [15]
  Y. Sagara, T. Mutai, I. Yoshikawa, K. Araki, J. Am. Chem. Soc. 129(2007) 1520-1521. doi: 10.1021/ja0677362
16. [16]
  G.Q. Zhang, J.W. Lu, M. Sabat, C.L. Fraser, J. Am. Chem. Soc. 132(2010) 2160-2162. doi: 10.1021/ja9097719
17. [17]
  Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27(2015) 6195-6201. doi: 10.1002/adma.201502442
18. [18]
  M. Jin, T.S. Chung, T. Seki, H. Ito, M.A. Garcia-Garibay, J. Am. Chem. Soc. 139(2017) 18115-18121. doi: 10.1021/jacs.7b11316
19. [19]
  A.N. Woodward, J.M. Kolesar, S.R. Hall, et al., J. Am. Chem. Soc.139(2017) 8467-8473. doi: 10.1021/jacs.7b01005
20. [20]
  S.Y. Park, Y. Kubota, K. Funabiki, M. Shiro, M. Matsui, Tetrahedron Lett. 50(2009) 1131-1135. doi: 10.1016/j.tetlet.2008.12.081
21. [21]
  G. Qian, Z.Y. Wang, Chem.-Asian J. 5(2010) 1006-1029. doi: 10.1002/asia.200900596
22. [22]
  L. Cheng, C. Wang, L.Z. Feng, K. Yang, Z. Liu, Chem. Rev. 114(2014) 10869-10939. doi: 10.1021/cr400532z
23. [23]
  P. Zhang, Z.Q. Guo, C.X. Yan, W.H. Zhu, Chin. Chem. Lett. 28(2017) 1952-1956. doi: 10.1016/j.cclet.2017.08.038
24. [24]
  D. Wu, Y.Z. Shen, J.H. Chen, et al., Chin. Chem. Lett. 28(2017) 1979-1982. doi: 10.1016/j.cclet.2017.07.004
25. [25]
  F.L. Song, R. Liang, J. Deng, Z.W. Liu, X.J. Peng, Chin. Chem. Lett. 28(2017) 1997-2000. doi: 10.1016/j.cclet.2017.08.023
26. [26]
  J.D. Luo, Z.L. Xie, J.W.Y. Lam, et al., Chem. Commun. (2001) 1740-1741.
27. [27]
  B.C. Lin, C.P. Cheng, Z.Q. You, C.P. Hsu, Phys. Chem. Chem. Phys. 13(2011) 20704-20713. doi: 10.1039/c1cp22535a
28. [28]
  F. Ciardelli, G. Ruggeri, A. Pucci, Chem. Soc. Rev. 42(2013) 857-870. doi: 10.1039/C2CS35414D
29. [29]
  Z. Mao, Z. Yang, Y. Mu, et al., Angew. Chem. Int. Ed. 54(2015) 6270-6273. doi: 10.1002/anie.201500426
30. [30]
  Q. Xiao, J. Zheng, M. Li, et al., Inorg. Chem. 53(2014) 11604-11615. doi: 10.1021/ic5016687
31. [31]
  T. Seki, N. Tokodai, S. Omagari, et al., J. Am. Chem. Soc. 139(2017) 6514-6517. doi: 10.1021/jacs.7b00587
32. [32]
  J.H. Chen, D.Y. Li, W.J. Chi, et al., Chem.-Eur. J. 24(2018) 3671-3676. doi: 10.1002/chem.201705780
33. [33]
  K.P. Guo, F. Zhang, S. Guo, et al., Chem. Commun. 53(2017) 1309-1312. doi: 10.1039/C6CC09186E
34. [34]
  W. Yang, C.L. Liu, S. Lu, et al., ChemistrySelect 2(2017) 9215-9221. doi: 10.1002/slct.201701997
35. [35]
  X. Cheng, D. Li, Z.Y. Zhang, H.Y. Zhang, Y. Wang, Org. Lett. 16(2014) 880-883. doi: 10.1021/ol403639n
36. [36]
  M. Tanioka, S. Kamino, A. Muranaka, et al., J. Am. Chem. Soc. 137(2015) 6436-6439. doi: 10.1021/jacs.5b00877
37. [37]
  H.W. Wu, P. Zhao, X. Li, et al., ACS Appl. Mater. Interfaces 9(2017) 3865-3872. doi: 10.1021/acsami.6b15939
38. [38]
  Z.W. Liu, K. Zhang, Q. Sun, et al., J. Mater. Chem. C 6(2018) 1377-1383. doi: 10.1039/C7TC04698G
39. [39]
  F.S. Zhang, L. Zhai, S.W. Feng, et al., Dyes Pigm. 156(2018) 140-148. doi: 10.1016/j.dyepig.2018.03.069
40. [40]
  S.Z. Mo, Q.T. Meng, S.L. Wan, et al., Adv. Funct. Mater. 27(2017) 1701210. doi: 10.1002/adfm.v27.28
41. [41]
  H.C. Zhu, J.Y. Huang, L. Kong, Y.P. Tian, J.X. Yang, Dyes Pigm.151(2018) 140-148. doi: 10.1016/j.dyepig.2017.12.053
42. [42]
  K. Jeong, S. Park, Y.D. Lee, et al., Adv. Mater. 25(2013) 5574-5580. doi: 10.1002/adma.201301901
43. [43]
  W. Li, X.P. Gan, D. Liu, et al., RSC Adv. 6(2016) 44599-44605. doi: 10.1039/C6RA05699G
44. [44]
  F. Hu, M.J. Cao, X. Ma, S.H. Liu, J. Yin, J. Org. Chem. 80(2015) 7830-7835. doi: 10.1021/acs.joc.5b01466
45. [45]
  H.Y. Zhuo, H.F. Su, Z.Z. Cao, et al., Chem.-Eur. J. 22(2016) 17619-17626. doi: 10.1002/chem.v22.49
46. [46]
  M.J. Lin, B. Fimmel, K. Radacki, F. Würthner, Angew. Chem. Int. Ed. 50(2011) 10847-10850. doi: 10.1002/anie.v50.46
47. [47]
  G. Qian, J. Qi, J.A. Davey, J.S. Wright, Z.Y. Wang, Chem. Mater. 24(2012) 2364-2372. doi: 10.1021/cm300938s
48. [48]
  K. Cai, Q.F. Yan, D.H. Zhao, Chem. Sci. 3(2012) 3175-3182. doi: 10.1039/c2sc21142d
49. [49]
  X. Zhang, B. Li, Z.H. Chen, Z.N. Chen, J. Mater. Chem. 22(2012) 11427-11441. doi: 10.1039/c2jm30394a
50. [50]
  S.F. Xue, Y.J. Wu, Y.S. Lu, et al., J. Mater. Chem. C 5(2017) 11700-11707. doi: 10.1039/C7TC04171C
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