Citation: Huijuan Chen, Weijie Chen, Yan Lin, Yuan Xie, Sheng Hua Liu, Jun Yin. Visible and near-infrared light activated azo dyes[J]. Chinese Chemical Letters, ;2021, 32(8): 2359-2368. doi: 10.1016/j.cclet.2021.03.020 shu

Visible and near-infrared light activated azo dyes

Huijuan Chen ^{a, b} ,
Weijie Chen ^{a, b} ,
Yan Lin ^d ,
Yuan Xie ^c ,
Sheng Hua Liu ^{a, b} ,
Jun Yin ^{a, b, c, *,}

a.
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, China
b.
Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, China
c.
Guangdong Provincial Key Laboratory of Radioactive and Rare Resource Utilization, Shaoguan 512026, China
d.
Department of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330013, China

yinj@mail.ccnu.edu.cn

Received Date: 9 January 2021
Revised Date: 4 March 2021
Accepted Date: 5 March 2021
Available Online: 9 March 2021

Figures(6)

The photoisomerization properties of azo derivatives have been widely used in the fields of materials and biology. One serious restriction to the development of functional azo-based materials is the necessity to trigger switching by UV light, which damage the corresponding surfaces and penetrate only partially through the matter. Therefore, developing the visible and near-infrared light activated azo switches can solve this problem. This review provides a summary of molecular design strategies for driving the isomerization of azo derivatives with visible light and near-infrared light: (1) smart design directly excited by visible light, (2) the addition of upconversion nanoparticles, (3) the employment of two-photon absorption, (4) indirect excitation in combination with metal sensitizer.
- Photochromism,
- Azo dyes,
- Visible light activation,
- Near-infrared light activation
1. [1]
  G.S. Hartley, Nature 140(1937) 281.
2. [2]
  D.J. van Dijken, P. Kovařríček, S.P. Ihrig, et al., J. Am. Chem. Soc. 137(2015) 914982-14991.
3. [3]
  C.E. Weston, R.D. Richardson, P.R. Haycock, et al., J. Am. Chem. Soc. 136(2014) 11878-11881. doi: 10.1021/ja505444d
4. [4]
  K. Hüll, J. Morstein, D. Trauner, Chem. Rev. 118(2018) 10710-10747. doi: 10.1021/acs.chemrev.8b00037
5. [5]
  J.B. Trads, K. Hüll, B.S. Matsuura, L. Laprell, et al., Angew. Chem. Int. Ed. 58(2019) 15421-15428. doi: 10.1002/anie.201905790
6. [6]
  S. Li, G. Han, W. Zhang, Macromolecules 51(2018) 4290-4297. doi: 10.1021/acs.macromol.8b00687
7. [7]
  J. Luo, S. Samanta, M. Convertino, N.V. Dokholyan, et al., ChemBioChem 19(2018) 2178-2185. doi: 10.1002/cbic.201800226
8. [8]
  A. Myrhammar, D. Rosik, A.E. Karlström, Bioconjugate Chem. 31(2020) 622-630. doi: 10.1021/acs.bioconjchem.9b00786
9. [9]
  Y.S. Chen, L. Li, W.J. Chen, et al., Chin. Chem. Lett. 30(2019) 1353-1360. doi: 10.1016/j.cclet.2019.02.003
10. [10]
  W.J. Chen, Y.L. Pan, J.H. Chen, et al., Chin. Chem. Lett. 29(2018) 1429-1435. doi: 10.1016/j.cclet.2018.08.011
11. [11]
  Y.P. Wang, Z.X. Zhang, M. Xie, et al., Dyes Pigments 129(2016) 100-108. doi: 10.1016/j.dyepig.2016.02.025
12. [12]
  D. Bléger, S. Hecht, Angew. Chem. Int. Ed. 54(2015) 11338-11349. doi: 10.1002/anie.201500628
13. [13]
  H.M.D. Bandara, S.C. Burdette, Chem. Soc. Rev. 41(2012) 1809. doi: 10.1039/C1CS15179G
14. [14]
  D.J. Warner, K.S. Keane, S.C. Blackstock, Bridged azobenzenes and their chemical applications, in: Z. Rappoport (Ed.), PATAI'S Chemistry of Functional Groups, John Wiley & Sons Inc., Hoboken, New Jersey, 2019, pp. 1-35.
15. [15]
  D. Bléger, J. Schwarz, A.M. Brouwer, et al., J. Am. Chem. Soc. 134(2012) 20597-20600. doi: 10.1021/ja310323y
16. [16]
  C. Knie, M. Utecht, F. Zhao, et al., Chem. Eur. J. 20(2014) 16492-16501. doi: 10.1002/chem.201404649
17. [17]
  S. Samanta, A.A. Beharry, O. Sadovski, etal., J. Am. Chem. Soc. 135(2013)9777-9784. doi: 10.1021/ja402220t
18. [18]
  D.B. Konrad, G. Savasci, L. Allmendinger, et al., J. Am. Chem. Soc. 142(2020) 6538-6547. doi: 10.1021/jacs.9b10430
19. [19]
  C.L. Forber, E.C. Kelusky, N.J. Bunce, et al., J. Am. Chem. Soc. 107(1985) 5884-5890. doi: 10.1021/ja00307a009
20. [20]
  R. Siewertsen, H. Neumann, B. Buchheim-Stehn, et al., J. Am. Chem. Soc. 131(2009) 15594-15595. doi: 10.1021/ja906547d
21. [21]
  M. Hammerich, C. Schütt, C. Stähler, et al., J. Am. Chem. Soc. 138(2016) 13111-13114. doi: 10.1021/jacs.6b05846
22. [22]
  M.S. Maier, K. Hüll, M. Reynders, et al., J. Am. Chem. Soc. 141(2019) 17295-17304. doi: 10.1021/jacs.9b08794
23. [23]
  S. Li, N. Eleya, A. Staubitz, Org. Lett. 22(2020) 1624-1627. doi: 10.1021/acs.orglett.0c00122
24. [24]
  H. Sell, C. Näther, R. Herges, Beilstein J. Org. Chem. 9(2013) 1-7. doi: 10.3762/bjoc.9.1
25. [25]
  R. Herges, W. Moormann, T. Tellkamp, et al., Angew. Chem. Int. Ed. 59(2020) 1-7. doi: 10.1002/anie.201914874
26. [26]
  P. Lentes, E. Stadler, F. Röhricht, et al., J. Am. Chem. Soc. 141(2019) 13592-13600. doi: 10.1021/jacs.9b06104
27. [27]
  A.A. Beharry, O. Sadovski, G.A. Woolley, J. Am. Chem. Soc. 133(2011) 19684-19687. doi: 10.1021/ja209239m
28. [28]
  S. Samanta, T.M. McCormick, S.K. Schmidt, et al., Chem. Commun. 49(2013) 10314-10316. doi: 10.1039/c3cc46045b
29. [29]
  O. Sadovski, A.A. Beharry, F. Zhang, et al., Angew. Chem. Int. Ed. 48(2009) 1484-1486. doi: 10.1002/anie.200805013
30. [30]
  Z. Ahmed, A. Siiskonen, M. Virkki, et al., Chem. Commun. 53(2017) 12520-12523. doi: 10.1039/C7CC07308A
31. [31]
  M. Dong, A. Babalhavaeji, S. Samanta, et al., Acc. Chem. Res. 48(2015) 2662-2670. doi: 10.1021/acs.accounts.5b00270
32. [32]
  J.S. Zhu, J.M. Larach, R.J. Tombari, et al., Org. Lett. 21(2019) 8765-8770. doi: 10.1021/acs.orglett.9b03387
33. [33]
  M.A. Kienzler, A. Reiner, E. Trautman, et al., J. Am. Chem. Soc. 135(2013) 17683-17686. doi: 10.1021/ja408104w
34. [34]
  S. Samanta, A. Babalhavaeji, M.X. Dong, et al., Angew. Chem. Int. Ed. 52(2013) 14127-14130. doi: 10.1002/anie.201306352
35. [35]
  C.E. Weston, R.D. Richardson, M.J. Fuchter, Chem. Commun. 52(2016) 4521-4524. doi: 10.1039/C5CC10380K
36. [36]
  M. Dong, A. Babalhavaeji, M.J. Hansen, et al., Chem. Commun. 51(2015) 12981-12984. doi: 10.1039/C5CC02804C
37. [37]
  M. Dong, A. Babalhavaeji, C.V. Collins, et al., J. Am. Chem. Soc. 139(2017) 13483-13486. doi: 10.1021/jacs.7b06471
38. [38]
  Y. Yang, R.P. Hughes, I. Aprahamian, J. Am. Chem. Soc. 134(2012) 15221-15224. doi: 10.1021/ja306030d
39. [39]
  H. Qian, Y.Y. Wang, D.S. Guo, et al., J. Am. Chem. Soc. 139(2017) 1037-1040. doi: 10.1021/jacs.6b10982
40. [40]
  Y. Yang, R.P. Hughes, I. Aprahamian, J. Am. Chem. Soc. 136(2014) 13190-13193. doi: 10.1021/ja508125n
41. [41]
  F. Deng, Z.C. Xu, Chin. Chem. Lett. 30(2019) 1667-1681. doi: 10.1016/j.cclet.2018.12.012
42. [42]
  J. Garcia-Amorós, S. Nonell, D. Velasco, Chem. Commun. 47(2011) 4022-4024. doi: 10.1039/c1cc10302d
43. [43]
  J. Garcia-Amorós, S. Nonell, D. Velasco, Chem. Commun. 48(2012) 3421-3423. doi: 10.1039/c2cc17782j
44. [44]
  J. Otsuki, K. Suwa, K. Narutaki, et al., J. Phys. Chem. A 109(2005) 8064-8069.
45. [45]
  J. Otsuki, K. Suwa, K.K. Sarker, et al., J. Phys. Chem. A 111(2007) 1403-1409. doi: 10.1021/jp066816p
46. [46]
  T. Wendler, C. Schütt, C. Näther, et al., J. Org. Chem. 77(2012) 3284-3287. doi: 10.1021/jo202688x
47. [47]
  J.A. Balam-Villarreal, B.J. López-Mayorga, D. Gallardo-Rosas, et al., Org. Biomol. Chem. 18(2020) 1657-1670. doi: 10.1039/C9OB02410G
48. [48]
  N.A. Simeth, S. Crespi, M. Fagnoni, et al., J. Am. Chem. Soc. 140(2018) 2940-2946. doi: 10.1021/jacs.7b12871
49. [49]
  A. Rennhack, E. Grahn, U.B. Kaupp, et al., ACS Chem. Biol. 12(2017) 2952-2957. doi: 10.1021/acschembio.7b00523
50. [50]
  E. Procházková, L. Cechová, J. Kind, et al., Chem. Eur. J. 24(2018) 492-498. doi: 10.1002/chem.201705146
51. [51]
  J. Garcia-Amorós, M. Díaz-Lobo, S. Nonell, et al., Angew. Chem. Int. Ed. 51(2012) 12820-12823. doi: 10.1002/anie.201207602
52. [52]
  S. Devi, M. Saraswat, S. Grewal, et al., J. Org. Chem. 83(2018) 4307-4322. doi: 10.1021/acs.joc.7b02604
53. [53]
  K. Rustler, P. Nitschke, S. Zahnbrecher, et al., J. Org. Chem. 85(2020) 4079-4088. doi: 10.1021/acs.joc.9b03097
54. [54]
  J. Garcia-Amorós, M.C.R. Castro, P. Coelho, et al., Chem. Commun. 49(2013) 11427-11429. doi: 10.1039/c3cc46736h
55. [55]
  J. Calbo, C.E. Weston, A.J.P. White, et al., J. Am. Chem. Soc. 139(2017) 1261-1274. doi: 10.1021/jacs.6b11626
56. [56]
  S. Crespi, N.A. Simeth, B. König, Nat. Rev. Chem. 3(2019) 133-146. doi: 10.1038/s41570-019-0074-6
57. [57]
  P. Kumar, A. Srivastava, C. Sah, et al., Chem. Eur. J. 25(2019) 11924-11932. doi: 10.1002/chem.201902150
58. [58]
  D. Kolarski, W. Szymanski, B.L. Feringa, Org. Lett. 19(2017) 5090-5093. doi: 10.1021/acs.orglett.7b02361
59. [59]
  A.D.W. Kennedy, I. Sandler, J. Andréasson, et al., Chem. Eur. J. 26(2020) 1103-1110. doi: 10.1002/chem.201904309
60. [60]
  E. Procházková, L. Cechová, J. Kind, et al., Chem. Eur. J. 24(2018) 492-498. doi: 10.1002/chem.201705146
61. [61]
  D.S. Wang, W.F. Zhao, Q. Wei, C.C. Zhao, et al., ChemPhotoChem 2(2018) 403-415. doi: 10.1002/cptc.201700233
62. [62]
  C.X. Yan, L.M. Shi, Z.Q. Guo, et al., Chin. Chem. Lett. 30(2019) 1849-1855. doi: 10.1016/j.cclet.2019.08.038
63. [63]
  Y. Zhang, Y. Zhang, G.B. Song, et al., Angew. Chem. Int. Ed. 58(2019) 18207-18211. doi: 10.1002/anie.201909870
64. [64]
  S.Q. He, J. Song, J.F. Liu, et al., Adv. Opt. Mater. 7(2019) 1900045. doi: 10.1002/adom.201900045
65. [65]
  D. Chen, W.J. Qin, H.X. Fang, et al., Chin. Chem. Lett. 30(2019) 1738-1744. doi: 10.1016/j.cclet.2019.08.001
66. [66]
  M. Izquierdo-Serra, M. Gascón-Moya, J.J. Hirtz, et al., J. Am. Chem. Soc. 136(2014) 8693-8701. doi: 10.1021/ja5026326
67. [67]
  G. Cabré, A. Garrido-Charles, M. Moreno, et al., Nat. Commun. 10(2019) 907. doi: 10.1038/s41467-019-08796-9
68. [68]
  J. Moreno, M. Gerecke, L. Grubert, et al., Angew. Chem. Int. Ed. 55(2016) 1544-1547. doi: 10.1002/anie.201509111
69. [69]
  S. Venkataramani, U. Jana, M. Dommaschk, et al., Science 331(2011) 445-448. doi: 10.1126/science.1201180
70. [70]
  M. Dommaschk, M. Peters, F. Gutzeit, et al., J. Am. Chem. Soc. 137(2015) 7552-7555. doi: 10.1021/jacs.5b00929
71. [71]
  M. Kurihara, A. Hirooka, S. Kume, et al., J. Am. Chem. Soc. 124(2002) 8800-8801. doi: 10.1021/ja026625+
72. [72]
  D.Y. Li, W.J. Chen, S.H. Liu, et al., Chin. Chem. Lett. 30(2020) 2891-2896.
73. [73]
  W.J. Chen, C. Zhang, X. Han, et al., J. Org. Chem. 84(2019) 14498-14507. doi: 10.1021/acs.joc.9b01976
74. [74]
  F.Y. Ye, W.J. Chen, Y.L. Pan, et al., Dyes Pigments 171(2019) 107746. doi: 10.1016/j.dyepig.2019.107746
75. [75]
  J. Xu, L. Shang, Chin. Chem. Lett. 29(2018) 1436-1444. doi: 10.1016/j.cclet.2017.12.020
76. [76]
  M.P. O'Hagan, J. Ramos-Soriano, S. Haldar, et al., Chem. Commun. 56(2020) 5186-5189. doi: 10.1039/D0CC01581D
77. [77]
  H. Zhou, Y.L. Xiao, X.C. Hong, Chin. Chem. Lett. 29(2018) 1425-1428. doi: 10.1016/j.cclet.2018.08.009
78. [78]
  L.J. Tang, J.Y. Xia, K.L. Zhong, et al., Dyes Pigments 178(2020) 108379. doi: 10.1016/j.dyepig.2020.108379
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