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咔唑用于检测硝基芳烃的荧光猝灭能力：综合实验分析与计算研究验证

Fluorescence quenching aptitude of carbazole for the detection of nitro-aromatics: a comprehensive experimental analysis and computational studies validation.

作者信息

Ahmed Ruby, Ali Farman, Alam Mohammad Jane, Tameem Mohd, Ali Abid, Ahmad Musheer, Khan Mohd Adeel

机构信息

Department of Applied Chemistry, Zakir Hussain College of Engineering and Technology, AMU Aligarh 202002 India

出版信息

RSC Adv. 2025 Aug 20;15(36):29479-29489. doi: 10.1039/d5ra01611h. eCollection 2025 Aug 18.

DOI:10.1039/d5ra01611h
PMID:40860098
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12377312/
Abstract

Fluorescence quenching studies of carbazole with nitroaromatics were studied and compared with 2-phenyl-1-phenanthro[9,10-]imidazole (M1). Carbazole (CBz) can sense all nitroaromatics, in particular picric acid (PA), whereas M1 responds to the ones having acidic hydrogen. The complex formation constant ( ) and limit of detection (LOD) were measured using the Stern-Volmer plot. Time-resolved fluorescence measurements reveal that quenching is static. We show that the mechanism of quenching involves ground state complex formation. The CBz-PA complex formation involves hydrogen bonding interaction between the N-H group of CBz and nitro group of PA, whereas M1-PA involves proton transfer from hydroxyl group of PA to nitrogen of imidazole in M1. The crystal structure of the ground-state complex (CBz-PA), its topology, and Hirshfeld surface analysis are also presented. Combined experimental and quantum chemical studies and wave function analysis were performed to study the non-covalent interactions and their role in charge transfer (CT) in the CBz-PA complex.

摘要

研究了咔唑与硝基芳烃的荧光猝灭，并与2-苯基-1-菲并[9,10 - ]咪唑（M1）进行了比较。咔唑（CBz）能够检测所有硝基芳烃，尤其是苦味酸（PA），而M1仅对具有酸性氢的硝基芳烃有响应。使用Stern - Volmer图测量了络合物形成常数（ ）和检测限（LOD）。时间分辨荧光测量表明猝灭是静态的。我们表明猝灭机制涉及基态络合物的形成。CBz - PA络合物的形成涉及CBz的N - H基团与PA的硝基之间的氢键相互作用，而M1 - PA涉及质子从PA的羟基转移到M1中咪唑的氮上。还给出了基态络合物（CBz - PA）的晶体结构、其拓扑结构和Hirshfeld表面分析。进行了结合实验和量子化学研究以及波函数分析，以研究CBz - PA络合物中的非共价相互作用及其在电荷转移（CT）中的作用。

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