A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism

被引：38
作者：
Xing, Miaomiao [1 ]
Wang, Kangnan [1 ]
Wu, Xiangwen [2 ]
Ma, Shuyue [1 ]
Cao, Duxia [1 ]
Guan, Ruifang [1 ]
Liu, Zhiqiang [3 ]
机构：
[1] Univ Jinan, Sch Mat Sci & Engn, Jinan 250022, Shandong, Peoples R China
[2] Shandong Normal Univ, Key Lab Mol & Nano Probes, Collaborat Innovat Ctr Functionalized Probes Chem, Coll Chem Chem Engn & Mat Sci,Minist Educ, Jinan 250014, Shandong, Peoples R China
[3] Shandong Univ, State Key Lab Crystal Mat, Jinan 250100, Shandong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 99期
基金：
中国国家自然科学基金;
关键词：
OPTICAL PROBE; WATER; CHEMOSENSOR; CYANIDE;
D O I：
10.1039/c9cc08174g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A ratiometric fluorescent probe for hydrazine based on a coumarin chalcone framework and a levulinic acid terminal group with a low detection limit (0.1 ppb, 0.003 mu M), a large ratiometric fluorescence change (I-465/I-575, 1265-fold enhancement) and a wide pH work range (3.0-12.0) was developed. The mechanism analysis of the isolated hydrazine product characterized by NMR, HRMS and the crystal structure indicates that the levulinic acid group is firstly removed by deprotection and then the dihydropyrazole ring is formed due to the addition and subsequent cyclization reaction in the presence of hydrazine.
引用
收藏
页码：14980 / 14983
页数：4
相关论文
共 42 条
[1]   Coumarin-Based Small-Molecule Fluorescent Chemosensors [J].
Cao, Duxia ;
Liu, Zhiqiang ;
Verwilst, Peter ;
Koo, Seyoung ;
Jangjili, Paramesh ;
Kim, Jong Seung ;
Lin, Weiying .
CHEMICAL REVIEWS, 2019, 119 (18) :10403-10519
[2]   A highly selective fluorescent probe based on coumarin for the imaging of N2H4 in living cells [J].
Chen, Song ;
Hou, Peng ;
Wang, Jing ;
Liu, Lei ;
Zhang, Qi .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2017, 173 :170-174
[3]   Hydrazine-Selective Chromogenic and Fluorogenic Probe Based on Levulinated Coumarin [J].
Choi, Myung Gil ;
Hwang, Jiyoung ;
Moon, Jung Ok ;
Sung, Jaeyoung ;
Chang, Suk-Kyu .
ORGANIC LETTERS, 2011, 13 (19) :5260-5263
[4]   Unique Tr-Output Optical Probe for Specific and Ultrasensitive Detection of Hydrazine [J].
Cui, Lei ;
Ji, Chunfei ;
Peng, Zhixing ;
Zhong, Lin ;
Zhou, Chaohui ;
Yan, Luliang ;
Qu, Song ;
Zhang, Shuping ;
Huang, Chusen ;
Qian, Xuhong ;
Xu, Yufang .
ANALYTICAL CHEMISTRY, 2014, 86 (09) :4611-4617
[5]   A simple but effective near-infrared ratiometric fluorescent probe for hydrazine and its application in bioimaging [J].
Dai, Xi ;
Wang, Zhao-Yang ;
Du, Zhi-Fang ;
Miao, Jun-Ying ;
Zhao, Bao-Xiang .
SENSORS AND ACTUATORS B-CHEMICAL, 2016, 232 :369-374
[6]   Analysis of hydrazine in drinldng water by isotope dilution gas chromatography/tandem, mass spectrometry with derivatization and liquid-liquid extraction [J].
Davis, William E., II ;
Li, Yongtao .
ANALYTICAL CHEMISTRY, 2008, 80 (14) :5449-5453
[7]   A coumarin based chemodosimetric probe for ratiometric detection of hydrazine [J].
Goswami, Shyamaprosad ;
Das, Sangita ;
Aich, Krishnendu ;
Sarkar, Deblina ;
Mondal, Tapan Kumar .
TETRAHEDRON LETTERS, 2014, 55 (16) :2695-2699
[8]   Surface-Enhanced Raman Spectroscopy-Based Approach for Ultrasensitive and Selective Detection of Hydrazine [J].
Gu, Xin ;
Camden, Jon P. .
ANALYTICAL CHEMISTRY, 2015, 87 (13) :6460-6464
[9]   A new near-infrared ratiometric fluorescent probe for hydrazine [J].
He, Yangyang ;
Li, Zhanxian ;
Shi, Bingjie ;
An, Zhen ;
Yu, Mingming ;
Wei, Liuhe ;
Ni, Zhonghai .
RSC ADVANCES, 2017, 7 (41) :25634-25639
[10]   A highly selective water-soluble optical probe for endogenous peroxynitrite [J].
Hou, Ji-Ting ;
Yang, Jin ;
Li, Kun ;
Liao, Ye-Xin ;
Yu, Kang-Kang ;
Xie, Yong-Mei ;
Yu, Xiao-Qi .
CHEMICAL COMMUNICATIONS, 2014, 50 (69) :9947-9950
12345