Synthesis and Application of Triazolothiadiazole-Coumarin Based Ratiometric Fluorescent Probes for Highly Selective Detection of H2S

被引:2
作者
Zhang, Chenglu [1 ]
Zhang, Yanpeng [1 ]
Wang, Huayu [1 ]
Zhao, Huanying [1 ]
Shang, Meitong [1 ]
Zhang, Lu [1 ]
Li, Xiangling [1 ]
Wang, Yiming [1 ]
机构
[1] Liaoning Normal Univ, Sch Chem Engn, Dalian 116029, Peoples R China
基金
中国国家自然科学基金;
关键词
hydrogen sulfide; Coumarin; ratiometric fluorescent probe; 1,3-SELENAZOLE; DERIVATIVES; THIADIAZOLE;
D O I
10.6023/cjoc202012024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three triazolothiadiazole-coumarin based ratiometric fluorescent probes (4a similar to 4c) for detection of H2S were designed and synthesized. Their structures were confirmed by IR, NMR and HRMS. Through fluorescence spectra, the probes expressed excellent fluorescent properties, which indicates that the design of the molecular structure was rational. The three probes all displayed highly quantum yields ( 0.6752, 0.6639, 0.6128), large Stokes shift (138, 131, 128 nm).They all exhibited high selectivity and sensitivity against H2S. The limit of detection were 0.19, 0.21 and 0.25 mu mol.L-1 respectively. Especially, probe 4a has the optimum efficiency,this result shows that the electron-donating group at 4-position of benzene is in favor of the optimization of fluorescent properties, owing to the accretion of electron density of the conjugated system. Besides, the three probes were all able to sense H2S by "naked-eye" according to the change in color from colorless to deep yellow. The probes can be applied to recognize H2S in actual water samples qualitatively and quantitatively.
引用
收藏
页码:2384 / 2392
页数:9
相关论文
共 27 条
[11]   Aromatization of 9,10-Dihydroacridine Derivatives: Discovering a Highly Selective and Rapid-Responding Fluorescent Probe for Peroxynitrite [J].
Li, Zhi-heng ;
Liu, Rui ;
Tan, Zheng-li ;
He, Lan ;
Lu, Zhong-lin ;
Gong, Bing .
ACS SENSORS, 2017, 2 (04) :501-505
[12]   Instantaneous fluorescent probe for the specific detection of H2S [J].
Lin, Xianfeng ;
Lu, Xiuhong ;
Zhou, Junliang ;
Ren, Hang ;
Dong, Xiaochun ;
Zhao, Weili ;
Chen, Zhongjian .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2019, 213 :416-422
[13]   A long-wavelength-emitting fluorescent probe for simultaneous discrimination of H2S/Cys/GSH and its bio-imaging applications [J].
Niu, Huawei ;
Ni, Bowen ;
Chen, Keke ;
Yang, Xiaopeng ;
Cao, Wenbo ;
Ye, Yong ;
Zhao, Yufen .
TALANTA, 2019, 196 :145-152
[14]   A novel ratiometric fluorescent probe for specific detection of HSO3- at nanomolar level through 1, 4-Michael addition [J].
Shen, Ronghua ;
Qian, Ying .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2020, 387
[15]   A Benzothiazole-Based Ratiometric Fluorescent Probe for Highly Selective Detection of Homocysteine and Its Bioimaging Application [J].
Shen, Youming ;
Gu, Biao ;
Liu, Xin ;
Tang, Yucai ;
Li, Haitao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) :2442-2449
[16]   Micelle-induced multiple performance improvement of fluorescent probes for H2S detection [J].
Tian, Haiyu ;
Qian, Junhong ;
Bai, Hongyan ;
Sun, Qian ;
Zhang, Lingyi ;
Zhang, Weibing .
ANALYTICA CHIMICA ACTA, 2013, 768 :136-142
[17]   A Highly Selective Fluorescent Probe for Hg2+ Based on a 1,8-Naphthalimide Derivative [J].
Tian, Meiju ;
Wang, Chunyan ;
Ma, Qiujuan ;
Bai, Yu ;
Sun, Jingguo ;
Ding, Chunfeng .
ACS OMEGA, 2020, 5 (29) :18176-18184
[18]   Fluorescent probe for sensitive discrimination of Hcy and Cys/GSH in living cells via dual-emission [J].
Xu, Shuang ;
Zhou, Junliang ;
Dong, Xiaochun ;
Zhao, Weili ;
Zhu, Quangang .
ANALYTICA CHIMICA ACTA, 2019, 1074 :123-130
[19]   Naphthalimide-sulfonamide fused dansyl-sulfonamide fluorescent probe for tracking glutathione of lysosome with a dual-emission manner [J].
Xu, Zhiqiang ;
Zhang, Ming-Xing ;
Li, Guangjin ;
Chen, Xiaoqiang ;
Liu, Sheng Hua ;
Chen, Haiyan ;
Yin, Jun .
DYES AND PIGMENTS, 2019, 171
[20]   Synthesis of triazolo-thiadiazole fluorescent organic nanoparticles as primary sensor toward Ag+ and the complex of Ag+ as secondary sensor toward cysteine [J].
Yan, Huijuan ;
Su, Haiyan ;
Tian, Demei ;
Miao, Fajun ;
Li, Haibing .
SENSORS AND ACTUATORS B-CHEMICAL, 2011, 160 (01) :656-661