Citation: Liu Mengdi, Ma Siyue, She Mengyao, Chen Jiao, Wang Zhaohui, Liu Ping, Zhang Shengyong, Li Jianli. Structural modification of BODIPY: Improve its applicability[J]. Chinese Chemical Letters, ;2019, 30(10): 1815-1824. doi: 10.1016/j.cclet.2019.08.028 shu

Structural modification of BODIPY: Improve its applicability

Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China

Author Bio: Mengdi Liu obtained her B.S. degree in 2017 from Northwest University. Currently, she starts her graduate study at Northwest University in Organic Chemistry under the supervision of Prof. Jianli Li. Her current research focuses on molecular recognition chemistry
Siyue Ma received her pH.D. degree in Organic Chemistry from the College of Chemistry and Materials Science, Northwest University, China, in 2019, under the supervision of Prof. Jianli Li. Her research interests focus on developing fluorescent chemosensors
Mengyao She received his B.S. degree in College of Chemistry and Materials Science, Northwest University, China, in 2012. He is currently a postdoctoral researcher in the College of Chemistry and Materials Science at Northwest University. His research interests focus on developing fluorescent chemosensors
Jiao Chen received her B.S. degree in School of Chemistry and Chemical Engineering from Southwest University, China. She is currently pursuing her pH.D. degree in Northwest University. Her researchinterests focus mainly on the development of near-infrared fluorescent probes for bioimaging
Zhaohui Wang received his B.S. degree in College of Chemistry and Materials Science from Northwest University, China, in 2017. He is currently pursuing his pH.D. degree in Northwest University. His current research interests focus on small-molecule fluorescent probes
Prof. Ping Liu was born in 1974, and is a professor at Northwest University, China. She received her pH.D. in Inorganic Chemistry from Northwest University, China, in 2005. Her current research interests include synthesis and study of new ligand and their functional complexes
Prof. Shengyong Zhang was born in 1939, and is the academician of National Academy of Engineering, China. He received his pH.D. in Chemistry from University ParisSud in 1982. He is now a professor at both Fourth Military Medical University and Northwest University. His research interests include asymmetric catalysis, synthesis of chiral drugs, resolution of racemic compounds, analysis, separation and determination of optical purity of chiral compounds
Prof. Jianli Li was born in 1973, and is a professor at Northwest University, China. He received his pH.D. in Organic Chemistry from Northwest University in 2007. His current research interests include synthesis and research methods for organic substance, fluorescent molecular devices, chemical and biological sensors and molecular recognition

lijianli@nwu.edu.cn

Received Date: 30 July 2019
Revised Date: 16 August 2019
Accepted Date: 16 August 2019
Available Online: 17 October 2019

Figures(22)

BODIPY has been considered a potential scaffold because of their neutral total charge, sharp absorption, and emission with high fluorescence quantum yield. However, the drawback of emission wavelength at less than 600 nm and hydrophobicity limit its application. One of the extremely interesting properties of BODIPY is that small modifications to their structures could be able to tune their properties, mainly including the absorption/emission wavelength and the hydrophilicity. This review focuses on the modification at different positions of BODIPY to improve the water-solubility and emission wavelength that describe their spectral, photophysical properties and applicability, which is helpful for the researchers to rationally design BODIPY dyes to adapt a wide range of applications.
- BODIPY,
- Near-infrared,
- Water solubility,
- Modification,
- Application
1. [1]
  X. Chen, F. Wang, J.Y. Hyun, et al., Chem. Soc. Rev. 45(2016) 2976-3016. doi: 10.1039/C6CS00192K
2. [2]
  J.L. Kolanowski, F. Liu, E.J. New, Chem. Soc. Rev. 47(2018) 195-208. doi: 10.1039/C7CS00528H
3. [3]
  Y. Xia, R. Zhang, Z. Wang, J. Tian, X. Chen, Chem. Soc. Rev. 46(2017) 2824-2843. doi: 10.1039/C6CS00675B
4. [4]
  D. Wu, A.C. Sedgwick, T. Gunnlaugsson, et al., Chem. Soc. Rev. 46(2017) 7105-7123. doi: 10.1039/C7CS00240H
5. [5]
  M. Gao, F.B. Yu, C.J. Lv, J. Choo, L.X. Chen, Chem. Soc. Rev. 46(2017) 2237-2271. doi: 10.1039/C6CS00908E
6. [6]
  Y. Chen, L. Li, W. Chen, H. Chen, J. Yin, Chin. Chem. Lett. 30(2019) 1353-1360. doi: 10.1016/j.cclet.2019.02.003
7. [7]
  Y. Zhu, W. Lin, W. Zhang, et al., Chin. Chem. Lett. 28(2017) 1875-1877. doi: 10.1016/j.cclet.2017.06.017
8. [8]
  D. Yue, M. Wang, F. Deng, et al., Chin. Chem. Lett. 29(2018) 648-656. doi: 10.1016/j.cclet.2018.01.046
9. [9]
  W. Qin, C. Xu, Y. Zhao, et al., Chin. Chem. Lett. 29(2018) 1451-1455. doi: 10.1016/j.cclet.2018.04.007
10. [10]
  von.A. Treibs, F.H. Kreuzer, Liebigs Ann. Chem. 718(1968) 208-223. doi: 10.1002/jlac.19687180119
11. [11]
  R.E. Hermes, T.H. Allik, S. Chandra, J.A. Hutchinson, Appl. Phys. Lett. 63(1993) 877-879. doi: 10.1063/1.109887
12. [12]
  N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 41(2012) 1130-1172. doi: 10.1039/C1CS15132K
13. [13]
  S. Kolemen, E.U. Akkaya, Coord. Chem. Rev. 354(2018) 121-134. doi: 10.1016/j.ccr.2017.06.021
14. [14]
  T. Kowada, H. Maeda, K. Kikuchi, Chem. Soc. Rev. 44(2015) 4953-4972. doi: 10.1039/C5CS00030K
15. [15]
  Y. Fan, M. Lu, X.A. Yu, et al., Anal. Chem. 91(2019) 6585-6592.
16. [16]
  H. He, Coord. Chem. Rev. 273-274(2014) 87-99. doi: 10.1016/j.ccr.2013.11.006
17. [17]
  K.D. Piatkevich, F.V. Subach, V.V. Verkhusha, Chem. Soc. Rev. 42(2013) 3441-3452. doi: 10.1039/c3cs35458j
18. [18]
  K.G. Chernov, T.A. Redchuk, E.S. Omelina, V.V. Verkhushaa, Chem. Rev. 117(2017) 6423-6446. doi: 10.1021/acs.chemrev.6b00700
19. [19]
  Z. Guo, S. Park, J. Yoon, I. Shin, Chem. Soc. Rev. 43(2014) 16-29. doi: 10.1039/C3CS60271K
20. [20]
  H. Xiang, J. Cheng, X. Ma, X. Zhou, J.J. Chruma, Chem. Soc. Rev. 42(2013) 6128-6185. doi: 10.1039/c3cs60029g
21. [21]
  A. Loudet, K. Burgess, Chem. Rev. 107(2007) 4891-4932. doi: 10.1021/cr078381n
22. [22]
  J.Z. Zhao, K.J. Xu, W.B. Yang, Z.J. Wang, F.F. Zhong, Chem. Soc. Rev. 44(2015) 8904-8939. doi: 10.1039/C5CS00364D
23. [23]
  H. Lu, J. Mack, Y. Yang, Z. Shen, Chem. Soc. Rev. 43(2014) 4778-4823. doi: 10.1039/C4CS00030G
24. [24]
  A. Kamkaew, S.H. Lim, H.B. Lee, et al., Chem. Soc. Rev. 42(2013) 77-88. doi: 10.1039/C2CS35216H
25. [25]
  A. Turksoy, D. Yildiz, E.U. Akkaya, Coord. Chem. Rev. 379(2019) 47-64. doi: 10.1016/j.ccr.2017.09.029
26. [26]
  M. Isik, T. Ozdemir, I.S. Turan, S. Kolemen, E.U. Akkaya, Org. Lett.15(2013) 216-219. doi: 10.1021/ol303306s
27. [27]
  G.K. Vegesna, S.R. Sripathi, J. Zhang, et al., ACS Appl. Mater. Interfaces 5(2013) 4107-4112. doi: 10.1021/am303247s
28. [28]
  I.W. Badon, J. Lee, T. Pegarro Vales, B.K. Cho, H.J. Kim, J. Photochem. Photobiol. A:Chem. 377(2019) 214-219. doi: 10.1016/j.jphotochem.2019.03.050
29. [29]
  L. Li, J. Han, B. Nguyen, K. Burgess, J. Org. Chem. 73(2008) 1963-1970. doi: 10.1021/jo702463f
30. [30]
  K.M. Bardon, S. Selfridge, D.S. Adams, et al., ACS Omega 3(2018) 13195-13199. doi: 10.1021/acsomega.8b01487
31. [31]
  P. Ashokkumar, H. Weisshoff, W. Kraus, K. Rurack, Angew. Chem. Int. Ed. 53(2014) 2225-2229. doi: 10.1002/anie.201307848
32. [32]
  A. Sampedro, A. Ramos-Torres, C. Schwoppe, et al., Angew. Chem. Int. Ed. 57(2018) 17235-17239. doi: 10.1002/anie.201804783
33. [33]
  U. Haldar, H.I. Lee, ACS Appl. Mater. Interfaces 11(2019) 13685-13693. doi: 10.1021/acsami.9b00408
34. [34]
  A. Nierth, A.Yu. Kobitski, G.U. Nienhaus, A. Jaschke, J. Am. Chem. Soc.132(2010) 2646-2654. doi: 10.1021/ja9084397
35. [35]
  H.W. Yao, X.Y. Zhu, X.F. Guo, H. Wang, Anal. Chem. 88(2016) 9014-9021. doi: 10.1021/acs.analchem.6b01532
36. [36]
  T. Kobayashi, T. Komatsu, M. Kamiya, et al., J. Am. Chem. Soc.134(2012) 11153-11160. doi: 10.1021/ja212125w
37. [37]
  L. Gai, J. Mack, H. Lu, et al., Chemistry 20(2014) 1091-1102. doi: 10.1002/chem.201303291
38. [38]
  J. Wang, Y. Li, Q. Gong, et al., J. Org. Chem. 84(2019) 5078-5090. doi: 10.1021/acs.joc.9b00020
39. [39]
  D. Taguchi, T. Nakamura, H. Horiuchi, M. Saikawa, T. Nabeshima, J. Org. Chem. 83(2018) 5331-5337. doi: 10.1021/acs.joc.8b00782
40. [40]
  D. Tian, F. Qi, H. Ma, et al., Nat. Commun. 9(2018) 2688. doi: 10.1038/s41467-018-05040-8
41. [41]
  L. Huang, Z. Li, Y. Zhao, et al., J. Am. Chem. Soc. 138(2016) 14586-14591. doi: 10.1021/jacs.6b05390
42. [42]
  F. Ali, S. Sreedharan, A.H. Ashoka, et al., Anal. Chem. 89(2017) 12087-12093. doi: 10.1021/acs.analchem.7b02567
43. [43]
  H. Xiong, H. Zuo, Y. Yan, et al., Adv. Mater. 29(2017) 1700131. doi: 10.1002/adma.201700131
44. [44]
  H. He, S. Ji, Y. He, et al., Adv. Mater. 29(2017) 1606690. doi: 10.1002/adma.201606690
45. [45]
  P. Verwilst, H. Kim, J. Seo, et al., J. Am. Chem. Soc. 139(2017) 13393-13403. doi: 10.1021/jacs.7b05878
46. [46]
  E. Palao, T. Slanina, L. Muchova, et al., J. Am. Chem. Soc. 138(2016) 126-133. doi: 10.1021/jacs.5b10800
47. [47]
  B. Shen, Y. Qian, Z. Qi, et al., J. Mater. Chem. B Mater. Biol. Med. 5(2017) 5854-5861. doi: 10.1039/C7TB01344B
48. [48]
  J.A. Peterson, C. Wijesooriya, E.J. Gehrmann, et al., J. Am. Chem. Soc.140(2018) 7343-7346. doi: 10.1021/jacs.8b04040
49. [49]
  C. Duan, M. Won, P. Verwilst, et al., Anal. Chem. 91(2019) 4172-4178. doi: 10.1021/acs.analchem.9b00224
50. [50]
  J. Zou, P. Wang, Y. Wang, et al., Chem. Sci. 10(2019) 268-276. doi: 10.1039/C8SC02443J
51. [51]
  Y.V. Zatsikha, N.O. Didukh, D. Nemez, et al., Chem. Commun. (Camb.) 53(2017) 7612-7615. doi: 10.1039/C7CC03332J
52. [52]
  S. Yamazawa, M. Nakashima, Y. Suda, R. Nishiyabu, Y. Kubo, J. Org. Chem. 81(2016) 1310-1315. doi: 10.1021/acs.joc.5b02720
53. [53]
  N. Zhao, S. Xuan, Z. Zhou, et al., J. Org. Chem. 82(2017) 9744-9750. doi: 10.1021/acs.joc.7b01940
54. [54]
  O. Suryani, Y. Higashino, J.Y. Mulyana, et al., Chem. Commun. (Camb.) 53(2017) 6784-6787. doi: 10.1039/C7CC02730C
55. [55]
  L. Jean-Gerard, W. Vasseur, F. Scherninski, B. Andrioletti, Chem. Commun. (Camb.) 54(2018) 12914-12929. doi: 10.1039/C8CC06403B
56. [56]
  S. Yuan, F. Wang, G. Yang, et al., Anal. Chem. 90(2018) 3914-3919. doi: 10.1021/acs.analchem.7b04787
57. [57]
  N. Adarsh, M.S. Krishnan, D. Ramaiah, Anal. Chem. 86(2014) 9335-9342. doi: 10.1021/ac502849d
58. [58]
  M. Strobl, A. Walcher, T. Mayr, I. Klimant, S.M. Borisov, Anal. Chem. 89(2017) 2859-2865. doi: 10.1021/acs.analchem.6b04045
59. [59]
  L. Li, L. Wang, H. Tang, D. Cao, Chem. Commun. (Camb.) 53(2017) 8352-8355. doi: 10.1039/C7CC04568A
60. [60]
  A.B. Kamkaew, K. Burgess, Chem. Commun. (Camb.) 51(2015) 10664-10667. doi: 10.1039/C5CC03649F
61. [61]
  C. Wu, X. Huang, Y. Tang, et al., Chem. Commun. (Camb.) 55(2019) 790-793. doi: 10.1039/C8CC07768A
62. [62]
  J. Pliquett, A. Dubois, C. Racoeur, et al., Bioconjug. Chem. 30(2019) 1061-1066. doi: 10.1021/acs.bioconjchem.8b00795
63. [63]
  X. Miao, W. Hu, T. He, et al., Chem. Sci. 10(2019) 3096-3102. doi: 10.1039/C8SC04840A
64. [64]
  X. Hu, C. Zhan, Y. Tang, et al., Chem. Commun. (Camb.) 55(2019) 6006-6009. doi: 10.1039/C9CC02148E
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