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Electrooxidation of rhodamine B hydrazide†
Nikita Belko,Hanna Maltanava,Anatol Lugovski,Sviatlana Fatykhava,Polina Shabunya,Anastasiya Tabolich,Sergey Poznyak
New Journal of Chemistry Pub Date : 07/28/2023 00:00:00 , DOI:10.1039/D3NJ02914J
Abstract

Spirocyclic rhodamines are promising sensors that exhibit turn-on fluorescence response to different stimuli including electric potential. Although rhodamine B hydrazide is often used as a building block for chemical and electrochemical sensors, the electrochemistry of this compound has not been reported. Herein, the electrochemical transformations of rhodamine B hydrazide are investigated using a combination of spectroelectrochemistry, liquid chromatography/mass spectrometry, and fluorescence spectroscopy. Pure rhodamine B hydrazide is a spirocyclic compound that is neither colored nor fluorescent. The electrooxidation of rhodamine B hydrazide in acetonitrile is shown to produce rhodamine B, a phtalazinone derivative, and a phenanthrenone derivative. These compounds exhibit fluorescence bands peaked at 580, 645, and 770 nm, respectively. The electrooxidation mechanism probably involves diazo, diazonium, and acylium intermediates. These findings imply a variety of applications for rhodamine B hydrazide as an electric potential sensor.

Graphical abstract: Electrooxidation of rhodamine B hydrazide
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