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
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
3. [3]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
4. [4]
  Jia-Mei Qin , Xue Li , Wei Lang , Fu-Hao Zhang , Qian-Yong Cao . An AIEgen nano-assembly for simultaneous detection of ATP and H₂S. Chinese Chemical Letters, 2024, 35(6): 108925-. doi: 10.1016/j.cclet.2023.108925
5. [5]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
6. [6]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
7. [7]
  Yuejiao An , Wenxuan Liu , Yanfeng Zhang , Jianjun Zhang , Zhansheng Lu . Revealing Photoinduced Charge Transfer Mechanism of SnO₂/BiOBr S-Scheme Heterostructure for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2407021-. doi: 10.3866/PKU.WHXB202407021
8. [8]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
9. [9]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
10. [10]
  Yong Shu , Xing Chen , Sai Duan , Rongzhen Liao . How to Determine the Equilibrium Bond Distance of Homonuclear Diatomic Molecules: A Case Study of H₂. University Chemistry, 2024, 39(7): 386-393. doi: 10.3866/PKU.DXHX202310102
11. [11]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
12. [12]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
13. [13]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
14. [14]
  Min LI , Xianfeng MENG . Preparation and microwave absorption properties of ZIF-67 derived Co@C/MoS₂ nanocomposites. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1932-1942. doi: 10.11862/CJIC.20240065
15. [15]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
16. [16]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
17. [17]
  Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi₂O₃ S型异质结在纯水体系中光催化合成H₂O₂性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012
18. [18]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
19. [19]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
20. [20]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(428)
HTML views(47)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142