Citation: Deng Fei, Xu Zhaochao. Heteroatom-substituted rhodamine dyes: Structure and spectroscopic properties[J]. Chinese Chemical Letters, ;2019, 30(10): 1667-1681. doi: 10.1016/j.cclet.2018.12.012 shu

Heteroatom-substituted rhodamine dyes: Structure and spectroscopic properties

Deng Fei ^a,b ,
Xu Zhaochao ^a,*,

a.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Author Bio: Fei Deng received his B.S. degree from Central China Normal University in 2013. He is currently a Ph.D. candidate in Dalian Institute of Chemical Physics, CAS, under the supervision of Prof. Zhaochao Xu. His research is focusing on the structure-fluorescence relationship of rhodamine dyes
Zhaochao Xu was born in Qingdao, China, in 1979. He received his PhD in 2006 from Dalian University of Technology under the supervision of Prof. Xuhong Qian. Subsequently, he joined Prof. Juyoung Yoon's group at Ewha Womans University as a postdoctoral researcher. Since October 2008, he was a Herchel Smith Research Fellow at University of Cambridge in Prof. David R. Spring's group. In 2011, he moved to Dalian Institute of Chemical Physics, CAS, where he is currently a Professor. His research is focusing on new fluorophore design and structure-fluorescence relationship, protein labelling and sensing, the development of fluorescent probes for the selective recognition and fluorescent imaging of biologically important species, and super-resolution fluorescent imaging

zcxu@dicp.ac.cn

Received Date: 7 November 2018
Revised Date: 2 December 2018
Accepted Date: 6 December 2018
Available Online: 13 October 2018

Figures(11)

Rhodamine is one class of most popular dyes used in fluorescence imaging due to the outstanding photoproperties including high brightness and photostability. In recent years, replacement the xanthene oxygen with other elements, especially silicon, has attracted great attentions in the development of new rhodamine derivatives. This review summarized the structures and photophysical properties of heteroatom-substituted rhodamines. We hope this review can help to understand the structure-property relationships of rhodamine dyes and then elucidate the way to create derivatives with improved photoproperties.
- Rhodamine,
- Heteroatom,
- Si-rhodamine,
- Optical properties,
- Fluorescent dyes
1. [1]
  Y. Kang, J.L. Fan, Q. Jin, et al., Chin. Chem. Lett. 28(2017) 1991-1993. doi: 10.1016/j.cclet.2017.08.054
2. [2]
  L.X. Peng, Y.X. Xu, P. Zou, Chin. Chem. Lett. 28(2017) 1925-1928. doi: 10.1016/j.cclet.2017.09.037
3. [3]
  P. Ning, W.J. Wang, M. Chen, Y. Feng, X.M. Meng, Chin. Chem. Lett. 28(2017) 1943-1951. doi: 10.1016/j.cclet.2017.09.026
4. [4]
  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
5. [5]
  S. Leng, Q.L. Qiao, Y. Gao, et al., Chin. Chem. Lett. 28(2017) 1911-1915. doi: 10.1016/j.cclet.2017.03.034
6. [6]
  F. Yang, C. Wang, L. Wang, et al., Chin. Chem. Lett. 28(2017) 2019-2022. doi: 10.1016/j.cclet.2017.07.030
7. [7]
  H. Zhou, Y. Xiao, X. Hong, Chin. Chem. Lett. 29(2018) 1425-1428. doi: 10.1016/j.cclet.2018.08.009
8. [8]
  W. Chen, Y. Pan, J. Chen, et al., Chin. Chem. Lett. 29(2018) 1429-1435. doi: 10.1016/j.cclet.2018.08.011
9. [9]
  X. Ma, L. Hu, X. Han, J. Yin, Chin. Chem. Lett. 29(2018) 1489-1492. doi: 10.1016/j.cclet.2018.06.022
10. [10]
  G. Gao, Y.W. Jiang, W. Sun, F.G. Wu, Chin. Chem. Lett. 29(2018) 1475-1485. doi: 10.1016/j.cclet.2018.07.004
11. [11]
  L.D. Lavis, Biochemistry 56(2017) 5165-5170. doi: 10.1021/acs.biochem.7b00529
12. [12]
  S. van de Linde, M. Heilemann, M. Sauer, Annu. Rev. Phys. Chem. 63(2012) 519-540. doi: 10.1146/annurev-physchem-032811-112012
13. [13]
  L.D. Lavis, R.T. Raines, ACS Chem. Biol. 3(2008) 142-155. doi: 10.1021/cb700248m
14. [14]
  M. Beija, C.A.M. Afonso, J.M.G. Martinho, Chem. Soc. Rev. 38(2009) 2410-2433. doi: 10.1039/b901612k
15. [15]
  L.X. Wu, K. Burgess, J. Org. Chem. 73(2008) 8711-8718. doi: 10.1021/jo800902j
16. [16]
  Z.H. Lei, X.R. Li, Y. Li, et al., J. Org. Chem. 80(2015) 11538-11543. doi: 10.1021/acs.joc.5b01746
17. [17]
  T. Ikeno, T. Nagano, K. Hanaoka, Chem.-Asian J. 12(2017) 1435-1446. doi: 10.1002/asia.201700385
18. [18]
  Y.Q. Sun, J. Liu, X. Lv, et al., Angew. Chem. Int. Ed. 51(2012) 7634-7636. doi: 10.1002/anie.201202264
19. [19]
  L. Yuan, W.Y. Lin, K.B. Zheng, L.W. He, W.M. Huang, Chem. Soc. Rev. 42(2013) 622-661. doi: 10.1039/C2CS35313J
20. [20]
  M.T.Z. Spence, I.D. Johnson, The Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 11th ed., Live Technologies Corporation, Carlsbad, CA, 2010.
21. [21]
  M.Y. Fu, Y. Xiao, X.H. Qian, D.F. Zhao, Y.F. Xu, Chem. Commun. (2008) 1780-1782.
22. [22]
  T. Egawa, K. Hanaoka, Y. Koide, et al., J. Am. Chem. Soc.133(2011) 14157-14159. doi: 10.1021/ja205809h
23. [23]
  Y. Koide, Y. Urano, K. Hanaoka, T. Terai, T. Nagano, J. Am. Chem. Soc.133(2011) 5680-5682. doi: 10.1021/ja111470n
24. [24]
  G. Lukinavicius, K. Umezawa, N. Olivier, et al., Nat. Chem. 5(2013) 132-139. doi: 10.1038/nchem.1546
25. [25]
  G. Lukinavicius, L. Reymond, K. Umezawa, et al., J. Am. Chem. Soc. 138(2016) 9365-9368. doi: 10.1021/jacs.6b04782
26. [26]
  N. Shimomura, Y. Egawa, R. Miki, T. Fujihara, Y. Ishimaru, T. Seki, Org. Biomol. Chem. 14(2016) 10031-10036. doi: 10.1039/C6OB01695B
27. [27]
  X.Q. Zhou, L. Lesiak, R. Lai, et al., Angew. Chem. Int. Ed. 56(2017) 4197-4200. doi: 10.1002/anie.201612628
28. [28]
  Y. Koide, Y. Urano, K. Hanaoka, T. Terai, T. Nagano, ACS Chem. Biol. 6(2011) 600-608. doi: 10.1021/cb1002416
29. [29]
  C. Aaron, C.C. Barker, J. Chem. Soc. 5(1963) 2655-2662.
30. [30]
  J.B. Grimm, A.J. Sung, W.R. Legant, et al., ACS Chem. Biol. 8(2013) 1303-1310. doi: 10.1021/cb4000822
31. [31]
  J.B. Grimm, B.P. English, J.J. Chen, et al., Nat. Methods 12(2015) 244-250. doi: 10.1038/nmeth.3256
32. [32]
  J.B. Grimm, A.K. Muthusamy, Y. Liang, et al., Nat. Methods 14(2017) 987-994. doi: 10.1038/nmeth.4403
33. [33]
  A.N. Butkevich, G.Y. Mitronova, S.C. Sidenstein, et al., Angew. Chem. Int. Ed. 55(2016) 3290-3294. doi: 10.1002/anie.201511018
34. [34]
  A.N. Butkevich, V.N. Belov, K. Kolmakov, et al., Chem.-Eur. J. 23(2017) 12114-12119. doi: 10.1002/chem.201701216
35. [35]
  G.Y. Mitronova, V.N. Belov, M.L. Bossi, et al., Chem.-Eur. J.16(2010) 4477-4488. doi: 10.1002/chem.200903272
36. [36]
  T. Pastierik, P. Sebej, J. Medalova, P. Stacko, P. Klan, J. Org. Chem. 79(2014) 3374-3382. doi: 10.1021/jo500140y
37. [37]
  Y. Koide, Y. Urano, K. Hanaoka, et al., J. Am. Chem. Soc. 134(2012) 5029-5031. doi: 10.1021/ja210375e
38. [38]
  T. Myochin, K. Hanaoka, S. Iwaki, et al., J. Am. Chem. Soc.137(2015) 4759-4765. doi: 10.1021/jacs.5b00246
39. [39]
  T. Wang, Q.J. Zhao, H.G. Hu, et al., Chem. Commun. 48(2012) 8781-8783. doi: 10.1039/c2cc34159j
40. [40]
  J.B. Grimm, T.A. Brown, A.N. Tkachuk, L.D. Lavis, ACS Cent. Sci. 3(2017) 975-985. doi: 10.1021/acscentsci.7b00247
41. [41]
  P. Horvath, P. Sebej, T. Solomek, P. Klan, J. Org. Chem. 80(2015) 1299-1311. doi: 10.1021/jo502213t
42. [42]
  A.N. Butkevich, G. Lukinavicius, E. D'Este, S.W. Hell, J. Am. Chem. Soc. 139(2017) 12378-12381. doi: 10.1021/jacs.7b06412
43. [43]
  H.L. Nie, L. Qiao, W. Yang, et al., J. Mater. Chem. B 4(2016) 4826-4831. doi: 10.1039/C6TB00938G
44. [44]
  X.Y. Chai, X.Y. Cui, B.G. Wang, et al., Chem.-Eur. J. 21(2015) 16754-16758. doi: 10.1002/chem.201502921
45. [45]
  X.Q. Zhou, R. Lai, J.R. Beck, H. Li, C.I. Stains, Chem. Commun. 52(2016) 12290-12293. doi: 10.1039/C6CC05717A
46. [46]
  M.W. Kryman, T.M. McCormick, M.R. Detty, Organometallics 35(2016) 1944-1955. doi: 10.1021/acs.organomet.6b00255
47. [47]
  M.R. Detty, P.N. Prasad, D.J. Donnelly, et al., Bioorg. Med. Chem. 12(2004) 2537-2544. doi: 10.1016/j.bmc.2004.03.029
48. [48]
  B. Calitree, D.J. Donnelly, J.J. Holt, et al., Organometallics 26(2007) 6248-6257. doi: 10.1021/om700846m
49. [49]
  T.Y. Ohulchanskyy, D.J. Donnelly, M.R. Detty, P.N. Prasad, J. Phys. Chem. B 108(2004) 8668-8672. doi: 10.1021/jp0370674
50. [50]
  M.W. Kryman, G.A. Schamerhorn, J.E. Hill, et al., Organometallics 33(2014) 2628-2640. doi: 10.1021/om500346j
51. [51]
  J. Liu, Y.Q. Sung, H.X. Zhang, et al., ACS Appl. Mater. Interfaces 8(2016) 22953-22962. doi: 10.1021/acsami.6b08338
52. [52]
  Y. Koide, M. Kawaguchi, Y. Urano, et al., Chem. Commun. 48(2012) 3091-3093. doi: 10.1039/c2cc18011a
53. [53]
  M.W. Kryman, G.A. Schamerhorn, K.Y. Yung, et al., Organometallics 32(2013) 4321-4333. doi: 10.1021/om400467s
54. [54]
  K. Kolmakov, E. Hebisch, T. Wolfram, et al., Chem.-Eur. J. 21(2015) 13344-13356. doi: 10.1002/chem.201501394
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