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]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
2. [2]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
3. [3]
  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
4. [4]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Weilai Yu , Chuanbiao Bie . Unveiling S-Scheme Charge Transfer Mechanism. Acta Physico-Chimica Sinica, 2024, 40(4): 2307022-0. doi: 10.3866/PKU.WHXB202307022
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . Green H₂O₂ synthesis via melamine-foam supported S-scheme Cd_0.5Zn_0.5In₂S₄/S-doped carbon nitride heterojunction: synergistic interfacial charge transfer and local photothermal effect. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-0. doi: 10.1016/j.actphy.2025.100093
13. [13]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . Efficient Photocatalytic Production of H₂O₂ over ZnO/D-A Conjugated Polymer S-scheme Heterojunction and Charge Transfer Dynamics Investigation. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-0. doi: 10.3866/PKU.WHXB202406027
14. [14]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
15. [15]
  Jiajie Cai , Chang Cheng , Bowen Liu , Jianjun Zhang , Chuanjia Jiang , Bei Cheng . CdS/DBTSO-BDTO S-scheme photocatalyst for H₂ production and its charge transfer dynamics. Acta Physico-Chimica Sinica, 2025, 41(8): 100084-0. doi: 10.1016/j.actphy.2025.100084
16. [16]
  Peng Li , Yuanying Cui , Zhongliao Wang , Graham Dawson , Chunfeng Shao , Kai Dai . Efficient interfacial charge transfer of CeO₂/Bi₁₉Br₃S₂₇ S-scheme heterojunction for boosted photocatalytic CO₂ reduction. Acta Physico-Chimica Sinica, 2025, 41(6): 100065-0. doi: 10.1016/j.actphy.2025.100065
17. [17]
  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
18. [18]
  Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti₃C₂ electrode material used for H₂S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
19. [19]
  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
20. [20]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(608)
HTML views(91)

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