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Experimental and computation study of thermal transformations of thienyl and furyl o- divinylbenzenes in acidic media

Distyrylbenzenes are known for their interesting photophysical and chemical properties [1]. Due to the extended delocalization of π electrons in the excited state they can form new complex structures that cannot be prepared by classical synthesis [2]. In addition to wellknown photochemical transformations of distyrylbenzenes, over the past years, their thermal transformations in neutral and acidic media were also studied. While thermal reaction in neutral medium did not indicate significant reactivity, acidic conditions can cause protonation of the double bond and the formation of new intramolecular products [3]. The aim of this study is to investigate in more detail the influence of the initial substrate on the mechanism of formation of the products of thermal protonated reactions. Therefore, the thermal reaction under acidic conditions of variously substituted furan derivatives of distyrylbenzene have been conducted and compared to their thiophene analogues thermal reactivity. The mechanism of the thermal reaction of furyl and thienyl o-divinylbenzenes under acidic conditions and the formation of products were explained in detail by quantum chemical calculations at the SMD/M06-2X/6- 311+G(2df, 2pd)//SMD/M06-2X/6-31G(d, p) level of theory and confirmed experimentally.

thermal transformations ; distyrylbenzenes ; reaction mechanism ; DFT calculations ; protonation

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