An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy

doi:10.6023/cjoc201910024

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1043-1049.DOI: 10.6023/cjoc201910024 Previous Articles Next Articles

pH调控下基于分子内电荷转移(ICT)机理的硫化氢荧光探针

朱继华^a,b, 张浩^a, 刘敏^a, 刘旌江^a, 廖原^a, 权正军^a, 王喜存^a

a 西北师范大学化学化工学院兰州 730070;
b 陇东学院化学化学工院甘肃庆阳 745000

收稿日期:2019-10-20 修回日期:2019-11-12 发布日期:2020-05-06
通讯作者: 权正军, 王喜存 E-mail:quanzhengjun@hotmail.com;wangxicun@nwnu.edu.cn
基金资助:
陇原青年创新创业人才工程（No.2019-39）和甘肃省高等学校科研（No.2018A-004）资助项目.

An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy

Zhu Jihua^a,b, Zhang Hao^a, Liu Min^a, Liu Jingjiang^a, Liao Yuan^a, Quan Zhengjun^a, Wang Xicun^a

a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
b College of Chemistry and Chemical Engineering, Longdong University, Qingyang, Gansu 745000

Received:2019-10-20 Revised:2019-11-12 Published:2020-05-06
Supported by:
Project supported by the Longyuan Youth Innovative and Entrepreneurial Talents Project (No. 2019-39) and the Research Project of Higher Education in Gansu Province (No. 2018A-004).

1. 201043S.pdf(1231KB)

Abstract

Hydrogen sulfide (H₂S) and pH play a most important role in vivo and environment. A fluorescent probe for fast and sensitive detection of H₂S and pH are of vital importance for research their functions. A naphthalimide-based fluorescent probe L has been designed and synthesized based on intramolecular charge transfer (ICT) mechanism by utilizing azide as recognition site. The probe L has demonstrated good stability in the pH range of 4~11. It showed satisfactory sensitivity and rapidly response (less than 3 min) to H₂S. An excellent linear relationship (R²=0.99823) displayed in the range of H₂S concentrations from 0 μmol·L^-1 to 20 μmol·L^-1 and the detection limit was 1.18 μmol·L^-1. Furthermore, in the present 30 equiv. H₂S, it was successfully applied to detection of pH with good linear relationship (R²=0.98764) in the pH range of 2~6.5. This methods provide a reference for detection of H₂S and pH value in the presence of 30 equiv. H₂S, which have potential application prospects in analytical detection and pathological analysis.

Key words: hydrogen sulfide, pH, fluorescent probe, theoretical calculations, ICT mechanism

Cite this article

Zhu Jihua, Zhang Hao, Liu Min, Liu Jingjiang, Liao Yuan, Quan Zhengjun, Wang Xicun. An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1043-1049.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Sjaastad, O.; Bakketeig, L. S. Cephalalgia 2006, 26, 466.
[2] Szabó, C. Nat. Rev. Drug Discovery 2007, 6, 917.
[3] Kaushik, R.; Ghosh, A.; Jose D. A. Coord. Chem. Rev. 2017, 347, 141.
[4] Zhou, C.; Qiu, B.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Li, Y. Chin. J. Org. Chem. 2017, 37, 92(in Chinese). (周婵, 邱波, 曾毅, 陈金平, 于天君, 李嫕, 有机化学, 2017, 37, 92.)
[5] Sun, L.; Wu, Y.; Chen, J.; Zhong, J.; Zeng, F.; Wu, S. Theranostics 2019, 9, 77.
[6] Abe, K.; Kimura, H. J. Neurosci. 1996, 16, 1066.
[7] Yang, G.; Wu, L.; Jiang, B.; Yang, W.; Qi, J.; Cao, K.; Zhang, S. Science 2008, 322, 587.
[8] Lavu, M.; Bhushan, S.; Lefer, D. J. Clin. Sci. 2011, 120, 219.
[9] de Sousa, M. C.; Vieira, R. B.; Dos Santos, D. S.; Carvalho, C. A.; Camargo, S. E.; Mancini, M. N.; de Oliveira, L. D. Arch. Oral Biol. 2015, 60, 600.
[10] Shi, W.; Pan, M.; Qiang, H.; Qiu, Q.; Huang, W.; Lin, H.; Qian, H.; Ge, L. Chem. Biol. Drug Des. 2017, 90, 167.
[11] Li, X.; Liu, Q.; Ye, S.; Wang, S.; Li, K.; Lv, G.; Peng, Y.; Qiu, L.; Lin, J. Chem. Biol. Drug Des. 2019, 94, 1494.
[12] Eto, K.; Asada, T.; Arima, K.; Makifuchi, T.; Kimura, H. Biochem. Biophys. Res. Commun. 2002, 293, 1485.
[13] Wang, H.; Yang, D.; Tan, R.; Zhou, Z. J.; Xu, R.; Zhang, J. F. Zhou, Y. Sens. Actuators, B 2017, 247, 883.
[14] Shi, D. T.; Zhou, D.; Zang, Y.; Li J.; Chen, G. R.; James, T. D.; He, X. P.; Tian, H. Chem. Commun. 2015, 51, 3653.
[15] Chen, S.; Ma, C.; Wang, D.-E.; Han, X.; Zhang, L.; Wang, J. Anal. Methods 2015, 7, 7646.
[16] Feng, X.; Zhang, T.; Liu, J.-T.; Miao, J.-Y.; Zhao, B.-X. Chem. Commun. 2016, 52, 3131.
[17] Cao, D.; Liu, Z.; Verwilst, P.; Koo, S.; Jangjili, P.; Kim, J. S.; Lin, W. Chem. Rev. 2019, 119, 10403.
[18] Peng, H.; Cheng, Y.; Dai, C.; King, A. L.; Predmore, B. L.; Lefer, D. J.; Wang, B. Angew. Chem., Int. Ed. 2011, 50, 9672.
[19] He, P.; Tang, L.-J; Zhong, K.-L.; Hou, S.-H.; Yan, X.-M. Chin. J. Org. Chem. 2017, 37, 423(in Chinese). (何平, 汤立军, 钟克利, 侯淑华, 燕小梅, 有机化学, 2017, 37, 423.)
[20] Wang, H.; Wu, X.-M.; Yang, S.-X.; Tian, H.-Y.; Liu, Y.-G.; Sun, B.-G. Dyes Pigm. 2019, 160, 757.
[21] Renault, K.; Renard, P.-Y.; Sabot, C. New J. Chem. 2017, 41, 10432.
[22] Li, H.; Feng, X.; Guo, Y.; Chen, D.; Li, R.; Ren, X. Sci. Rep. 2014, 4, 4366.
[23] Jun, M. E.; Roy, B.; Ahn, K. H. Chem. Commun. 2011, 47, 7583.
[24] Chen, H.; Gong, X.; Liu, X.; Li, Z.; Zhang, J.; Yang, X.-F. Sens. Actuators, B 2019, 281, 542.
[25] Chen, Y.; Zhu, C.; Yang, Z. Chen, J.; He, Y.; Jiao, Y. Angew. Chem., Int. Ed. 2013, 52, 1688.
[26] Lippert, R.; New, E. L.; Chang, C. J. J. Am. Chem. Soc. 2011, 133, 10078.
[27] Lippert, A. R. J. Inorg. Biochem. 2014, 133, 136.
[28] Platt, F. M. Nature. 2014, 510, 68.
[29] Liu, X.; Su, Y.; Tian, H.; Yang, L.; Zhang, H.; Song, X.; Foley, J. W. Anal. Chem. 2017, 89, 7038.
[30] Xue, Z.; Zhao, H.; Liu, J.; Han, J.; Han, S. ACS Sens. 2017, 2, 436.
[31] Sun, T.; Xia, L.; Huang, J.; Gu, Y.; Wang, P. Talanta 2018, 187, 295.
[32] Fan, F.; Jing, J.; Chen, X. Chin. J. Org. Chem. 2014, 34, 2178(in Chinese). (范方禄, 靖金球, 陈雪梅, 有机化学, 2014, 34, 2178.)
[33] Peng, S.; Zhong, T.; Guo, T.; Shu, D.; Meng, D.; Liu, H.; Guo, D. New J. Chem. 2018, 42, 5185.
[34] Pancholi, J.; Hodson, D. J.; Jobe, K.; Rutter, G. A.; Goldup, S. M.; Watkinson, M. Chem. Sci. 2014, 5, 3528.

pH调控下基于分子内电荷转移(ICT)机理的硫化氢荧光探针

An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yong Zhang, Zhigao Tian, Lin Huang, Qiufei Hou, Honghong Fan, Wanqiang Wang. Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 561-572.
[2]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[3]	Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.
[4]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[5]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[6]	Kangbo Feng, Jiong Chen, Shuangxi Gu, Haifeng Wang, Fen'er Chen. New Progress of Fully Continuous Flow Reaction Technologies in Pharmaceutical Synthesis (2019~2022) [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 378-397.
[7]	Chunyan She, Anjing Wang, Shan Liu, Wenming Shu, Weichu Yu. Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 481-507.
[8]	Zhiyou Huang, Ping Yang, Bo He, Wenxia Ou, Siyu Yuan. Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 309-315.
[9]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[10]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[11]	Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp³)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17.
[12]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.
[13]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[14]	Xianqiang Meng, Yi Yang, Wanjie Liang, Jingtao Wang, Rongkui Zhang, Hui Liu. Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 224-231.
[15]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.