Synthesis of Dicyanovinyl-Substituted 1-(2-Pyridyl)pyrazoles: Design of a Fluorescent Chemosensor for Selective Recognition of Cyanide

被引：73

作者：

Orrego-Hernandez, Jessica ^{[1
]}

Portilla, Jaime ^{[1
]}

机构：

[1] Univ Los Andes, Dept Chem, Bioorgan Cpds Res Grp, Carrera 1 18A-10, Bogota 111711, Colombia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 24期

关键词：

AGGREGATION-INDUCED EMISSION; SOLVENT-FREE CONDITIONS; REGIOSELECTIVE SYNTHESIS; ONE-POT; 1,1'-BINAPHTHYL SCAFFOLD; SENSITIVE DETECTION; ANION DETECTION; PYRAZOLE; DERIVATIVES; PROBE;

D O I：

10.1021/acs.joc.7b02460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fluorescence "turn-off" probe has been designed and successfully applied to detect cyanide (CN-) based on a Michael-type nucleophilic addition reaction and intramolecular charge transfer (ICT) mechanism. For this research, a family of 3-aryl-4-(2,2-dicyanovinyl)-1-(2-pyridinyl)pyrazoles as donor-pi-acceptor (D-pi-A) systems have been synthesized in 58-66% overall yield, by a three-step synthesis sequence starting from p-substituted acetophenones. The substituted p-methoxyphenyl showed good fluorescence emission and large Stokes shifts in different solvents due to its greater ICT. Likewise, this probe evidenced high selectivity and sensitivity and fast recognition for CN- with a detection limit of 6.8 mu M. HRMS analysis, H-1 NMR titration experiments, and TD-DFT calculations were performed to confirm the mechanism of detection and fluorescence properties of the chemodosimeter of CN-. Additionally, fluorescent test paper was conveniently used to detect cyanide in aqueous solution.

引用

页码：13376 / 13385

页数：10

共 77 条

[1] Pyrazole-3(4)-carbaldehyde: synthesis, reactions and biological activity
Abdel-Wahab, Bakr F.
Khidre, Rizk E.
Farahat, Abdelbasset A.
[J]. ARKIVOC, 2011, : 196 - 245
[2] A new ICT and CHEF based visible light excitable fluorescent probe easily detects in vivo Zn2+
Aich, Krishnendu
Goswami, Shyamaprosad
Das, Sangita
Das Mukhopadhyay, Chitrangada
[J]. RSC ADVANCES, 2015, 5 (39) : 31189 - 31194
[3] [Anonymous], 2009, GAUSSIAN 09 USERS RE
[4] Asymmetric bimetallic ruthenium(II) complexes selectively sense cyanide in water through significant modulation of their ground and excited state properties
Bar, Manoranjan
Maity, Dinesh
Das, Kunalkanti
Baitalik, Sujoy
[J]. SENSORS AND ACTUATORS B-CHEMICAL, 2017, 251 : 208 - 223
[5] Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report)
Brouwer, Albert M.
[J]. PURE AND APPLIED CHEMISTRY, 2011, 83 (12) : 2213 - 2228
[6] Fundamental aspects of property tuning in push-pull molecules
Bures, Filip
[J]. RSC ADVANCES, 2014, 4 (102) : 58826 - 58851
[7] Mixed-ligand Zn(II) complexes of 1-phenyl-3-methyl-4-forrnylpyrazole-5-one and various aminoheterocycles: Synthesis, structure and photoluminescence properties
Burlov, Anatolii S.
Koshchienko, Yurii V.
Makarova, Nadezhda I.
Kuz'menko, Tat'yana A.
Chesnokov, Vasilii V.
Kiskin, Mikhail A.
Nikolaevskii, Stanislav A.
Garnovskii, Dmitrii A.
Uraev, Ali I.
Vlasenko, Valerii G.
Metelitsa, Anatolii V.
[J]. SYNTHETIC METALS, 2016, 220 : 543 - 550
[8] Simple access toward 3-halo- and 3-nitro-pyrazolo [1,5-a]pyrimidines through a one-pot sequence
Castillo, Juan-Carlos
Rosero, Hernan-Alejandro
Portilla, Jaime
[J]. RSC ADVANCES, 2017, 7 (45): : 28483 - 28488
[9] 6-(Aryldiazenyl)pyrazolo[1,5-a]pyrimidines as Strategic Intermediates for the Synthesis of Pyrazolo[5,1-b]purines
Castillo, Juan-Carlos
Estupinan, Diego
Nogueras, Manuel
Cobo, Justo
Portilla, Jaime
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) : 12364 - 12373
[10] Highly sensitive detection of low-level water content in organic solvents and cyanide in aqueous media using novel solvatochromic AIEE fluorophores
Chen, Wei
Zhang, Zhiyun
Li, Xin
Agren, Hans
Su, Jianhua
[J]. RSC ADVANCES, 2015, 5 (16) : 12191 - 12201

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