Citation: YANG Wen-Jing, ZHANG Yu-Jin, WANG Chuan-Kui. Optical Properties and Responsive Mechanism of 4-Amino-1,8-Naphthalimide-Based Two-Photon Fluorescent Probe for Sensing Hydrogen Sulfide[J]. Acta Physico-Chimica Sinica, ;2015, 31(12): 2303-2309. doi: 10.3866/PKU.WHXB201510233 shu

Optical Properties and Responsive Mechanism of 4-Amino-1,8-Naphthalimide-Based Two-Photon Fluorescent Probe for Sensing Hydrogen Sulfide

1.
College of Physics and Electronics, Shandong Normal University, Jinan 250014, P. R. China

Corresponding author: WANG Chuan-Kui,
Received Date: 3 August 2015
Available Online: 23 October 2015
Fund Project: 国家重点基础研究发展规划项目(973)(2011CB808100)资助 (973)(2011CB808100)

Response theory was used to investigate one-photon absorption (OPA) and emission, and twophoton absorption (TPA) of two novel truncated two-photon fluorescent probes AcHS-1,2 in the presence and absence of H₂S using density functional theory in combination with the polarizable continuum model . Changes in the optical properties, including large redshifts of the OPA, TPA, and emission peak positions were observed when the probes reacted with H₂S, indicating that AcHS-1,2 make effective and selective chemosensors for H₂S. We have also demonstrated that the terminal group on the probes influenced their nonlinear optical properties (AcHS-1: n-butyl group and AcHS-2: hydroxyethyl group). The responsive mechanism of AcHS-1,2 for sensing H₂S was analyzed by studying the charge variations between the charge transfer and ground states of the free molecules and their reaction products using Mulliken population analysis. Importantly, this mechanism was attributed to an intramolecular charge transfer.
- Fluorescent probe,
- Two-photon absorption,
- H₂S,
- Intramolecular charge transfer
1. [1]
  (1) He, X. W.; Long, H. T.; Yuan, G.; Xu, X. J.; Zhou, Y. W. Acta Phys. -Chim. Sin. 2010, 26 (4), 1082. [何湘伟, 龙海涛, 袁谷, 徐筱杰, 周亚伟. 物理化学学报, 2010, 26 (4), 1082.] doi: 10.3866/PKU.WHXB20100416
2. [2]
  (2) Li, H.; Liu, X. M.; Geng, B.; Pan, C. S.; Qi, Y. F.; Wu, S. Y.; Tang, C. S. J. Peking Univ. Health Sci. 2006, 38 (2), 140. [李虹, 刘新民, 耿彬, 潘春水, 齐永芬, 吴胜英, 唐朝枢. 北京大学学报(医学版), 2006, 38 (2), 140.]
3. [3]
  (3) Krishnan, N.; Fu, C.; Pappin, D. J.; Tonks, N. K. Sci. Signal. 2011, No. 4, 86.
4. [4]
  (4) Liao, F.; Zheng, Y.; Geng, B. Prog. Physiol. Sci. 2012, 43 (2), 111. [廖峰, 郑扬, 耿彬. 生理科学进展, 2012, 43 (2), 111.]
5. [5]
  (5) Morita, T.; Perrella, M. A.; Lee, M. E. Proc. Natl. Acad. Sci. U. S. A. 1995, 92 (5), 1475. doi: 10.1073/pnas.92.5.1475
6. [6]
  (6) Wang, M.; Zhu, J.; Yang, P.; Dong, J. D.; Zhang, L. L.; Zhang, X. R.; Zhang, L. J. Neurosci. Res. 2015, 93, 487. doi: 10.1002/jnr.v93.3
7. [7]
  (7) Michele, F. D.; Luchetti, S.; Bernardi, G.; Romeo, E.; Longone, P. Front. Neuroendocrin. 2013, 34, 132.
8. [8]
  (8) Li, L.; Rose, P.; Moore, P. K. Annu. Rev. Pharmacol. 2011, 51, 169. doi: 10.1146/annurev-pharmtox-010510-100505
9. [9]
  (9) Lowicka, E.; Beltowski, J. Pharmacol. Rep. 2007, 59, 4.
10. [10]
  (10) Szabo, C. Nat. Rev. Drug Discov. 2007, 6, 917. doi: 10.1038/nrd2425
11. [11]
  (11) Choi, M. G.; Cha, S.; Lee, H.; Jeon, H. L.; Chang, S. K. Chem. Commun. 2009, 7390.
12. [12]
  (12) Lawrence, N. S.; Davis, J.; Jiang, L.; Jones, T. G. J.; Davies, S. N.; Compton, R. G. Electroanalysis 2000, 18, 1453.
13. [13]
  (13) Mitchell, T. W.; Savage, J. C.; Gould, D. H. J. Appl. Toxicol. 1993, 13, 389.
14. [14]
  (14) Ishigami, M.; Hiraki, K.; Umemura, K.; Ogasawara, Y.; Ishii, K.; Kimura, H. Antioxid. Redox. Sign. 2009, 11, 205. doi: 10.1089/ars.2008.2132
15. [15]
  (15) Wang, Y.; Zhao, Q.; Sun, J.; Lü , J. Z.; Tang, B. Prog. Chem. 2013, 25 (2), 179. [王栩, 赵谦, 孙娟, 吕建政, 唐波. 化学进展, 2013, 25 (2), 179.]
16. [16]
  (16) Fu, X. Y.; Shao, G. S.; Han, R. C.; Ma, Y.; Xue, F. M.; Yang, F.; Fu, L. M.; Zhang, J. P.; Wang, Y. Acta Phys. -Chim. Sin. 2012, 28 (10), 2480. [符小艺, 邵光胜, 韩荣成, 马严, 薛富民, 杨帆, 付立民, 张建平, 王远. 物理化学学报, 2012, 28 (10), 2480.] doi: 10.3866/PKU.WHXB201208161
17. [17]
  (17) Li, H.; Hao, Z. Y.; Meng, X.; Zhu, Y. C. Chin. J. Chem. Phys. 2015, 28 (2), 235. doi: 10.1063/1674-0068/28/cjcp1410184
18. [18]
  (18) Tong, Y.; Dai, C. G.; Ren, Y.; Luo, S. W. Chin. J. Chem. Phys. 2015, 28 (3), 277. doi: 10.1063/1674-0068/28/cjcp1412217
19. [19]
  (19) Wu, Z. S, ; Li, Z.; Yang, L.; Han, J. H.; Han, S. F. Chem. Commun. 2012, 48, 10120. doi: 10.1039/c2cc34682f
20. [20]
  (20) Chen, Y. G.; Zhu, C. C.; Yang, Z. H.; Chen, J. J.; He, Y. F.; Jiao, Y.; He, W.; Qiu, L.; Cen, J. J.; Guo, Z. J. Angew. Chem. 2013, 125, 1732. doi: 10.1002/ange.v125.6
21. [21]
  (21) Liu, X. L.; Du, X. J.; Dai, C. G.; Song, Q. H. J. Org. Chem. 2014, 79, 9481. doi: 10.1021/jo5014838
22. [22]
  (22) Ding, H. J.; Sun, J.; Zhang, Y. J.; Wang, C. K. Chem. Phys. Lett. 2014, 591, 142. doi: 10.1016/j.cplett.2013.11.015
23. [23]
  (23) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.01; Gaussian Inc.: Wallingford, CT, 2009.
24. [24]
  (24) WIREs. Comput. Mol. Sci. 2014, 4, 269. doi: 10.1002/wcms.2014.4.issue-3
25. [25]
  (25) Zhang, Y. J.; Zhang, Q. Y.; Ding, H. J.; Song, X. N.; Wang, C. K. Chin. Phys. B 2015, 24, 023301. doi: 10.1088/1674-1056/24/2/023301
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