Study of the Electrochemical Behavior of Merocyanine and Merocarbocyanine Salts and Their Transformation into Π-Electron Donor Molecules, Namely Tetrathiatetraazafulvalenes

Manel Khiat; Fatima-Zohra Zradni; Souad Kasmi-Mir; Alejandro Baeza

doi:10.22146/ijc.58132

Study of the Electrochemical Behavior of Merocyanine and Merocarbocyanine Salts and Their Transformation into Π-Electron Donor Molecules, Namely Tetrathiatetraazafulvalenes

https://doi.org/10.22146/ijc.58132

Manel Khiat^(1*), Fatima-Zohra Zradni⁽²⁾, Souad Kasmi-Mir⁽³⁾, Alejandro Baeza⁽⁴⁾

(1) Laboratory of Organic Synthesis, Physico-Chemistry, Biomolecules and Environment (LSPBE), Department of Chemical Engineering, Faculty of Chemistry, University of Sciences and Technology of Oran “Mohamed Boudiaf”- USTOMB, El Mnaouar، BP 1505, Bir El Djir 31000 Oran, Algeria
(2) Laboratory of Organic Synthesis, Physico-Chemistry, Biomolecules and Environment (LSPBE), Department of Chemical Engineering, Faculty of Chemistry, University of Sciences and Technology of Oran “Mohamed Boudiaf”- USTOMB, El Mnaouar، BP 1505, Bir El Djir 31000 Oran, Algeria
(3) Faculty of Science, Department of Chemistry, Saad Dahlab University Blida 1, 9000 Blida, Algeria
(4) Institute of Organic Synthesis (ISO), Faculty of Sciences, University of Alicante Carretera of San Vicente del Raspeig, s/n, 03690 Alicante, Spain
(*) Corresponding Author

Abstract

An electrochemical study using the cyclic voltammetry method was carried out on some previously prepared merocyanines salts, namely thiazolideniumsulfonate salts 5a-b, and thiazolidenium chloride salts 6a-b, and merocarbocyanines salts, namely alkylidenthiazolidenium sulfonate salt 5c, and alkylidenthiazolidenium chloride salt 6c. These salts are transformed by dimerization in situ in a voltammetric cell into tetrathiatetraazafulvalenes (TTTAFs) 7a-b, 7’a-b, 8c, and 8'c supposed to be π-electron donor molecules due to the existing conjugation in their structure. The structure of all new chemically synthesized molecules was confirmed by IR, ¹H-NMR, ¹³C-NMR, and MS. The transformation of salts into TTTAF was confirmed by a reversible voltammogram curve and the variation of observed potentials.

Keywords

rhodanines; thiazolium salts; merocyanines; tetrathiafulvalenes; dithiadiazafulvalenes; cyclic voltammetry

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DOI: https://doi.org/10.22146/ijc.58132