Citation: Cao Jianfang, Sun Wen, Fan Jiangli. Insights into bishemicyanines with long emission wavelengths and high sensitivity in viscous environments[J]. Chinese Chemical Letters, ;2020, 31(6): 1402-1405. doi: 10.1016/j.cclet.2019.10.006 shu

Insights into bishemicyanines with long emission wavelengths and high sensitivity in viscous environments

Cao Jianfang ^a,b ,
Sun Wen ^a ,
Fan Jiangli ^a,*,

a.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
b.
School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou 121001, China

fanjl@dlut.edu.cn

Received Date: 3 September 2019
Revised Date: 8 October 2019
Accepted Date: 9 October 2019
Available Online: 14 October 2019

Figures(4)

A systematic spectral analysis was presented for bishemicyanine dyes (Hsd and D2) and monohemicyanine dyes (Hs and DSMI). The bishemicyanine dyes displayed long emission wavelengths, large Stokes shifts, low background quantum yields in aqueous solutions and high sensitivity in viscous environments. Better understanding of the structure-property relationships could benefit the design of improved dyes. Computational studies on these dyes revealed the three conjugated forms of bishemicyanines are in equilibrium due to two positive charges and a branched bulk substituent. Bishemicyanines possessed obviously lower rotating energy barrier of C-C bond rotation compared to the monohemicyanine dyes. Moreover, the synergetic effects of the rotation about the ϕ₄ bond, ϕ₅ bond and ϕ₇ bond of the bishemicyanines (Hsd and D2) lead to lower fluorescence quantum yields in a free state and larger fluorescence quantum yield enhancements in viscous environment compared to that of monohemicyanine dyes (Hs and DSMI). The results demonstrate a foundation for interpretation of the behavior of the dyes, thus providing guidelines for future of new bishemicyanine fluorophores with specific applications.
- Bishemicyanine dyes,
- Long emission wavelength,
- Low background quantum yield,
- Rotating energy barrier,
- Density functional calculations
1. [1]
  Y.V. Suseela, N. Narayanaswamy, S. Pratihar, T. Govindaraju, Chem. Soc. Rev. 47(2018) 1098-1131. doi: 10.1039/C7CS00774D
2. [2]
  S. Samanta, S. Halder, G. Das, Anal. Chem. 90(2018) 7561-7568. doi: 10.1021/acs.analchem.8b01181
3. [3]
  T. Zhu, J. Du, W. Cao, J. Fan, X. Peng, Ind. Eng. Chem. Res. 55(2016) 527-533. doi: 10.1021/acs.iecr.5b04214
4. [4]
  J. Cui, Y. Yao, C. Chen, et al., Chin. Chem. Lett. 30(2019) 1071-1074. doi: 10.1016/j.cclet.2018.12.031
5. [5]
  W. Sun, S. Guo, C. Hu, J. Fan, X. Peng, Chem. Rev. 116(2016) 7768-7817. doi: 10.1021/acs.chemrev.6b00001
6. [6]
  Y. Huang, T. Cheng, F. Li, et al., J. Phys. Chem. B 106(2002) 10041-10050. doi: 10.1021/jp0208788
7. [7]
  T. Shim, M.H. Lee, D.Kim, H.S.Kim, K.B.Yoon, J.Phys.Chem.B 113(2009)966-969. doi: 10.1021/jp8073333
8. [8]
  K. Bi, R. Tan, R. Hao, et al., Chin. Chem. Lett. 30(2019) 545-548. doi: 10.1016/j.cclet.2018.11.020
9. [9]
  Z. Pillai, P.K. Sudeep, K.G. Thomas, Res. Chem. Intermed. 29(2003) 293-305. doi: 10.1163/156856703764929958
10. [10]
  C.Q. Zhu, S.J. Zhuo, H. Zheng, et al., Analyst 129(2004) 254-258. doi: 10.1039/b313463f
11. [11]
  L. Guo, M.S. Chan, D. Xu, et al., ACS Chem. Biol. 10(2015) 1171-1175. doi: 10.1021/cb500927r
12. [12]
  K. Zhou, M. Ren, B. Deng, W. Lin, New J. Chem. 41(2017) 11507-11511. doi: 10.1039/C7NJ02270K
13. [13]
  G. Hungerford, A. Allison, D. McLoskey, et al., J. Phys. Chem. B 113(2009) 12067-12074. doi: 10.1021/jp902727y
14. [14]
  Y. Shiraishi, T. Inoue, T. Hirai, Langmuir 26(2010) 17505-17512. doi: 10.1021/la1028993
15. [15]
  B. Wandelt, P. Cywinski, G.D. Darling, B.R. Stranix, Biosens. Bioelectron. 20(2005) 1728-1736. doi: 10.1016/j.bios.2004.06.045
16. [16]
  J.T. Miao, C. Fan, R. Sun, Y.J. Xu, J.F. Ge, J. Mater. Chem. B 2(2014) 7065-7072.
17. [17]
  L. Yuan, W. Lin, Y. Yang, H. Chen, J. Am. Chem. Soc. 134(2012) 1200-1211. doi: 10.1021/ja209292b
18. [18]
  D. Wu, Y. Shen, J. Chen, et al., Chin. Chem. Lett. 28(2017) 1979-1982. doi: 10.1016/j.cclet.2017.07.004
19. [19]
  F. Liu, T. Wu, J. Cao, et al., Chem.-Eur. J. 19(2013) 1548-1553. doi: 10.1002/chem.201202646
20. [20]
  S.I. Reja, I.A. Khan, V. Bhalla, M. Kumar, Chem. Commun. (Camb.) 52(2016) 1182-1185. doi: 10.1039/C5CC08217J
21. [21]
  L. Yu, Q. Yang, Y. Tang, Chin. Chem. Lett. 30(2019) 694-697. doi: 10.1016/j.cclet.2018.10.011
22. [22]
  Y. Jin, X. Tian, L. Jin, et al., Anal. Chem. 90(2018) 3276-3283. doi: 10.1021/acs.analchem.7b04813
23. [23]
  A.J. Chung, P.S. Deore, S. Al-Abdul-Wahid, et al., J. Org. Chem. 84(2019) 2261-2268. doi: 10.1021/acs.joc.9b00066
24. [24]
  Z.Z. Gao, J. Kan, Z. Tao, B. Bian, X. Xiao, New J. Chem. 42(2018) 15420-15426. doi: 10.1039/C8NJ03344G
25. [25]
  X. Lv, J. Liu, Y. Liu, et al., Chem. Commun. (Camb.) 47(2011) 12843-12845. doi: 10.1039/c1cc15721c
26. [26]
  X.J. Feng, P.L. Wu, F. Bolze, et al., Org. Lett. 12(2010) 2194-2197. doi: 10.1021/ol100474b
27. [27]
  S. Sun, Y. Yuan, Z. Li, et al., New J. Chem. 38(2014) 3600-3605. doi: 10.1039/C4NJ00068D
28. [28]
  Z. Li, S. Sun, Z. Yang, et al., Biomaterials 34(2013) 6473-6481. doi: 10.1016/j.biomaterials.2013.05.020
29. [29]
  A.D. Boese, N.C. Handy, J. Chem. Phys. 116(2002) 9559-9569. doi: 10.1063/1.1476309
30. [30]
  J.F. Cao, C. Hu, W. Sun, et al., RSC Adv. 4(2014) 13385-13394. doi: 10.1039/c3ra46612d
31. [31]
  O. Treutler, R. Ahlrichs, J. Chem. Phys. 102(1995) 346-354. doi: 10.1063/1.469408
32. [32]
  J.F. Cao, C. Hu, F. Liu, et al., ChemPhysChem 14(2013) 1601-1608. doi: 10.1002/cphc.201300049
33. [33]
  M.K. Kuimova, G. Yahioglu, J.A. Levitt, K. Suhling, J. Am. Chem. Soc. 130(2008) 6672-6673. doi: 10.1021/ja800570d
34. [34]
  J.F. Cao, T. Wu, C. Hu, et al., Phys. Chem. Chem. Phys. 14(2012) 13702-13708. doi: 10.1039/c2cp42122d
35. [35]
  A.C. Benniston, A. Harriman, V.L. Whittle, M. Zelzer, Eur. J. Org. Chem. 2010(2010) 523-530.
36. [36]
  G.L. Silva, V. Ediz, D. Yaron, B.A. Armitage, J. Am. Chem. Soc. 129(2007) 5710-5718. doi: 10.1021/ja070025z
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