Citation: ZHOU Dan-Hong, LI Miao-Miao, CUI Li-Li. Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite[J]. Acta Physico-Chimica Sinica, ;2013, 29(07): 1453-1460. doi: 10.3866/PKU.WHXB201304244 shu

Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite

1.
Institute of Chemistry for Functionalized Materials, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning Province, P. R. China

Received Date: 18 March 2013
Available Online: 24 April 2013

A heptamethine cyanine dye containing an organoselenium functional group is a near-IR fluorescent probe that operates based on photoinduced electron transfer (PET). This probe can be used for highly sensitive and selective monitoring of peroxynitrite under physiological conditions. In this paper, the photophysical properties and PET mechanism of the probe molecule were investigated by time-dependent density functional theory (TD-DFT) calculations. The results indicated that the excitation in the fluorophore involves an electron transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). The HOMO level of the recognizer moiety increased in energy above that of the HOMO occupied with a single electron of the fluorophore, leading to transfer of one electron to the heptamethine cyanine moiety, which quenched the fluorescence emission. After the Se moiety was oxidized, the HOMO level of the recognizer moiety decreased in energy, the PET process was prevented, and the fluorescence emission was recovered. It was further proposed that the PET was contributed to by the p electron of the nitrogen atom in the aniline moiety of the probe. The PET efficiency is regulated by the oxidation and reduction events of the organoselenium moiety, resulting in“on-off”fluorescence emission.
- Heptamethine cyanine dye,
- Organoselenium,
- Fluorescence sensor,
- Photoinduced electron transfer,
- Time-dependent density functional theory,
- Excited state
1. [1]
  
  (1) de Silva, A. P.; Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A.J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev.1997, 97, 1515. doi: 10.1021/cr960386p
2. [2]
  (2) Zaheer, A.; Lenkinskl, R. E.; Mahmood, A.; Jones, A. G.;Cantley, L. C.; Frangioni, J. V. Nat. Biotechnol. 2001, 19, 1148.doi: 10.1038/nbt1201-1148
3. [3]
  (3) Tang, B.; Yu, F.; Li, P.; Tong, L.; Duan, X.; Xie, T.;Wang, X.J. Am. Chem. Soc. 2009, 131, 3016. doi: 10.1021/ja809149g
4. [4]
  (4) recki, T.; Patonay, G.; Strekowski, L. J. Heterocycl. Chem.1996, 33, 1871. doi: 10.1002/jhet.v33:6
5. [5]
  (5) Yang, C.; Shimelis, O.; Zhou, X.; Li, G.; Bayle, C.; Nertz, M.;Lee, H.; Strekowski, L.; Patonay, G.; Couderc, F.; Giese, R.W.J. Chromatogr. A 2002, 979, 307. doi: 10.1016/S0021-9673(02)01441-3
6. [6]
  (6) Gallaher, D. L.; Johnson, M. E. Analyst 1999, 124, 1541.doi: 10.1039/a904541d
7. [7]
  (7) Yu, F. B.; Li, P.; Li, G. Y.; Zhao, G. J.; Chu, T. S.; Han, K. L.J. Am. Chem. Soc. 2011, 133, 11030. doi: 10.1021/ja202582x
8. [8]
  (8) Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.;Hafeman, D. G.; Hoekstra,W. G. Science 1973, 179, 588.doi: 10.1126/science.179.4073.588
9. [9]
  (9) Nogueira, C.W.; Zeni, G.; Rocha, J. B. Chem. Rev. 2004, 104,6255. doi: 10.1021/cr0406559
10. [10]
  (10) Mugesh, G.; du Mont,W.W.; Sies, H. Chem. Rev. 2001, 101,2125. doi: 10.1021/cr000426w
11. [11]
  (11) Weller, A. Pure Appl. Chem. 1968, 16, 115. doi: 10.1351/pac196816010115
12. [12]
  (12) Rehm, D.;Weller, A. Isr. J. Chem. 1970, 8, 259
13. [13]
  (13) Terai, T.; Kikuchi, K.; Iwasawa, S.; Kawabe, T.; Hirata, Y.;Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 6938.
14. [14]
  (14) Petsalakis, I. D.; Lathiotakis, N. N.; Theodorakopoulos, G.J. Mol. Struct.-Theochem 2008, 867, 64. doi: 10.1016/j.theochem.2008.07.025
15. [15]
  (15) Salman, H.; Tal, S.; Chuvilov, Y.; Solovey, O.; Abraham, Y.;Kapon, M.; Suwinska, K.; Eichen, Y. Inorg. Chem. 2006, 45 (14), 5315. doi: 10.1021/ic051897+
16. [16]
  (16) Han, F.; Chi, L.; Liang, X.; Ji, S.; Liu, S.; Zhou, F.;Wu, Y.; Han,K.; Zhao, J.; James, T. D. J. Org. Chem. 2009, 74 (3), 1333.doi: 10.1021/jo8025669
17. [17]
  (17) Chi, L. N.;Wu, Y. B.; Zhang, X.; Ji, S. M.; Shao, J. Y.; Guo, H.M.;Wang, X.; Zhao, J. Z. J. Fluores. 2010, 20, 1255.doi: 10.1007/s10895-010-0677-2
18. [18]
  (18) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
19. [19]
  (19) dbout, N.; Salahub, D. R.; Andzelm, J.;Wimmer, E. Can. J. Chem. 1992, 70, 560. doi: 10.1139/v92-079
20. [20]
  (20) Foster, J. P.;Weinhold, F. J. Am. Chem. Soc. 1980, 102 (24),7211.
21. [21]
  (21) Gross, E. K. U.; Kohn,W. Phys. Rev. Lett. 1985, 55 (26), 2850.doi: 10.1103/PhysRevLett.55.2850
22. [22]
  (22) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys.1998, 109, 8218. doi: 10.1063/1.477483
23. [23]
  (23) Vosko, S. H.;Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.doi: 10.1139/p80-159
24. [24]
  (24) Xu,W. H.; Zhang, Y.; Liu,W. J. Science in China B-Chemistry2009, 39 (11), 1484. [许文华, 张勇, 刘文剑. 中国科学B辑: 化学, 2009, 39 (11), 1484.]
25. [25]
  (25) Becke, A. D. Phys. Rev. A 1988, 38 (6), 3098. doi: 10.1103/PhysRevA.38.3098
26. [26]
  (26) Perdew, J. P. Phys. Rev. B 1986, 33, 8832.
27. [27]
  (27) Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346.doi: 10.1063/1.469408
28. [28]
  (28) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Chem. Phys.2001, 114, 5691. doi: 10.1063/1.1354187
29. [29]
  (29) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem.2003, 24, 669. doi: 10.1002/jcc.10189
30. [30]
  (30) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03,Revision E.01; Gaussian Inc.:Wallingford, CT, 2010.
31. [31]
  (31) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09,Revision B.01; Gaussian Inc.:Wallingford, CT, 2004.
32. [32]
  (32) Eckert, F.; Klamt, A. AIChE J. 2002, 48, 369.
33. [33]
  (33) Awuah, S. G.; Polreis, J.; Biradar, V.; You, Y. Org. Lett. 2011, 13 (15), 3884. doi: 10.1021/ol2014076
34. [34]
  (34) Wang, Y. L.;Wu, G. S. Acta Phys. -Chim. Sin. 2007, 23, 1831.[王溢磊, 吴国是. 物理化学学报, 2007, 23, 1831.] doi: 10.1016/S1872-1508(07)60086-2
35. [35]
  (35) Liu, X. J.;Wang, N,; Cheng, H. Acta Phys. -Chim. Sin. 2011, 27,1640. [刘小君, 王宁, 程浩. 物理化学学报, 2011, 27,1640.] doi: 10.3866/PKU.WHXB20110718
36. [36]
  (36) Liu, X. J.; Lin, T.; Gao, S.W.; Ma, R.; Zhang, J. Y.; Cai, X. C.;Yang, L.; Teng, F. Acta Phys. -Chim. Sin. 2012, 28, 1337.[刘小君, 林涛, 高少伟, 马睿, 张晋悦, 蔡新晨, 杨磊,滕枫. 物理化学学报, 2012, 28, 1337.] doi: 10.3866/PKU.WHXB201204092
37. [37]
  (37) Wang, F. J.; Zhou, D. H.; Zuo, S. Y.; Cao, J. F.; Peng, X. J. Acta Phys. -Chim. Sin. 2012, 28, 1645. [王凤娇, 周丹红, 左士颖,曹建芳, 彭孝军. 物理化学学报, 2012, 28, 1645.] doi: 10.3866/PKU.WHXB201205083
38. [38]
  (38) Ren, X. F.; Ren, A. M.;Wang, Q.; Feng, J. K. Acta Phys. -Chim. Sin. 2010, 26, 110. [任雪峰, 任爱民, 王钦, 封继康.物理化学学报, 2010, 26, 110.] doi: 10.3866/PKU.WHXB20100103
39. [39]
  (39) Zhao, P.; Xu, L. C.; Ma, L. Acta Phys. -Chim. Sin. 2011, 27,2541. [赵平, 绪连彩, 马丽. 物理化学学报, 2011, 27,2541.] doi: 10.3866/PKU.WHXB20111021
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