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]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
2. [2]
  Shangqian Zhang , Jiaxuan Li , Xuan Hu , Zelong Chen , Junliang Dong , Chenhao Hu , Shuang Chao , Yinghua Lv , Yuxin Pei , Zhichao Pei . H₂S and NIR light-driven nanomotors induce disulfidptosis for targeted anticancer therapy by enhancing disruption of tumor metabolic symbiosis. Chinese Chemical Letters, 2025, 36(1): 110314-. doi: 10.1016/j.cclet.2024.110314
3. [3]
  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
4. [4]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
5. [5]
  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
6. [6]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
7. [7]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(498)
HTML views(63)

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