Non-aqueous electrochemistry of rhodamine B acylhydrazone

文献信息

发布日期 2023-12-15
DOI 10.1039/D3NJ04711C
影响因子 3.591
作者

Nikita Belko, Hanna Maltanava, Anatol Lugovski, Polina Shabunya, Sviatlana Fatykhava, Evgeny Bondarenko, Pavel Chulkin, Sergey Poznyak


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摘要

Rhodamine B hydrazide and rhodamine B acylhydrazone are spirocyclic compounds that provide a versatile framework for developing chemical and electrochemical sensors with turn-on optical response. Herein, we explore how a simple conversion of rhodamine B hydrazide into rhodamine B acylhydrazone can change its electrochemical behavior. Non-aqueous electrochemistry of rhodamine B acylhydrazone is studied using cyclic voltammetry, in situ electron spin resonance spectroscopy, bulk electrolysis, spectrophotometry, and liquid chromatography/mass spectrometry. Cyclic voltammograms of the dye demonstrate two reversible electrooxidation waves peaked at 0.54 and 0.69 V (vs. Fc+/Fc). In situ electron spin resonance spectroscopy data suggest that the electrooxidation mechanism of rhodamine B acylhydrazone involves several free radical intermediates. Bulk electrolysis of rhodamine B acylhydrazone generates a variety of products in a potential-dependent manner. Although rhodamine B acylhydrazone and rhodamine B hydrazide have similar molecular structures, they exhibit differing electrochemical behavior. In particular, protection of the hydrazide moiety by the propan-2-ylidene substituent in rhodamine B acylhydrazone molecules drastically increases the reversibility of electrooxidation. The obtained results can be used for developing new sensors with desired electrochemical properties based on the derivatives of rhodamine B hydrazide.

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来源期刊

New Journal of Chemistry

New Journal of Chemistry
CiteScore: 5.3
自引率: 3.7%
年发文量: 2153

NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.

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