An attempt to synthesize a terthienyl-based analog of indacenedithiophene (IDT): unexpected synthesis of a naphtho[2,3-b]thiophene derivative?

RSC Advances Pub Date: 2021-03-08 DOI: 10.1039/D1RA00659B

Abstract

We report herein our attempt to synthesize an analog of indacenedithiophene (IDT) based on a tetraphenylhexyl substituted, covalently bridged syn-terthienyl unit. Instead of the expected compound the adopted synthetic route led to the formation of an unexpected, new naphtho[2,3-b]thiophene derivative. The structure of this compound was fully characterized by NMR and HRMS as well as single crystal X-ray diffraction and its electronic properties have been analyzed by UV-vis absorption spectroscopy and cyclic voltammetry. A possible mechanism for the formation of this compound is also proposed on the basis of detailed theoretical investigations.

Graphical abstract: An attempt to synthesize a terthienyl-based analog of indacenedithiophene (IDT): unexpected synthesis of a naphtho[2,3-b]thiophene derivative
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