Effects of substituents on fluorometric detection of cyanide anions by indolium–coumarin dyads

文献情報

出版日 2015-08-27

DOI 10.1039/C5CP03877D

インパクトファクター 3.676

著者

Masaya Nakamura, Takayuki Hirai

原文を見る

要旨

We synthesized an indolium–coumarin dyad (1) and its derivatives with –Cl (2), –N(CH3)2 (3), or –NO2 (4) substituent, and used them for fluorometric detection of cyanide anions (CN−) in aqueous media. All of the dyads exhibit fluorescence enhancement by CN−via a nucleophilic interaction of CN− with the indolium carbon atoms. Their fluorescence response and selectivity to CN−, however, depend strongly on the substituents. Ab initio calculation and kinetic analysis were performed to verify the behaviors. Substitution of electron-withdrawing groups (2 and 4) increases the electrophilicity of the indolium carbon. This decreases the activation enthalpy for the nucleophilic interaction with CN− and facilitates rapid CN− sensing. Compound 4 with very high electrophilicity, however, also promotes nucleophilic interaction with OH− in the solution, resulting in decreased CN− selectivity. As a result of this, the –Cl-substituted compound 2 containing the indolium carbon with appropriate electrophilicity facilitates rapid (within 1 min) and selective CN− detection.

掲載誌

Physical Chemistry Chemical Physics

CiteScore: 5.5

自己引用率: 10.3%

年間論文数: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Effects of substituents on fluorometric detection of cyanide anions by indolium–coumarin dyads

文献情報

おすすめジャーナル

関連文献

Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction

An attempt to provide an environmentally friendly solvent selection guide for olefin metathesis

Solvents for sustainable chemical processes

Design and evaluation of switchable-hydrophilicity solvents

Back cover

Biodegradability of 27 pyrrolidinium, morpholinium, piperidinium, imidazolium and pyridinium ionic liquid cations under aerobic conditions

Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids

Non-toxic catalysts for ring-opening polymerizations of biodegradable polymers at room temperature for biohybrid materials

Long-chain aliphatic polyesters from plant oils for injection molding, film extrusion and electrospinning

Integrated electrocatalytic processing of levulinic acid and formic acid to produce biofuel intermediate valeric acid

こちらもおすすめ

4-アミノフェノール酸ナトリウム水和物とは何ですか？

Methyl 3-methyl-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-histidinateの代替品はありますか？

4-Boc-2-哌嗪甲酸の市場動向や研究トレンドはどうですか？

4,4'-二羟甲基联苯の物理化学的性質は何ですか？

5-甲硫基戊腈はどの業界で使用されていますか？

CAS番号1311961-50-8の化合物はどのように合成されますか？

6-ブロモベンジジミダゾール-2-カルビルデオキシドはどのように保存すればよいですか？

Boc-N-甲基氨甲环酸とは何ですか？

乙基三氟硼酸钾はどのように合成されますか？

2-フロウロ-5-クロロ-4-アミノフェノールはどのように保存すればよいですか？

掲載誌

Physical Chemistry Chemical Physics

おすすめ化合物

(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid

(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-(tert-butyl)phenyl)butanoic acid

N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide

Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

2-(2,6-Dihydroxyphenyl)benzene-1,3-diol

おすすめサプライヤー