Conjugated small organic molecules: synthesis and characterization of 4-arylpyrazole-decorated dibenzothiophenes?

New Journal of Chemistry Pub Date: 2020-05-07 DOI: 10.1039/D0NJ01887B

Abstract

4-Arylpyrazole-decorated dibenzothiophenes have been synthesized. The synthesis involves the treatment of 2,8-dibromodibenzothiophene with pyrazole under Ullmann-type amination conditions for the dual C–N bond formation. The selective bromination of the resulting dual C–N bonded 2,8-dipyrazolyldibenzothiophene, and the subsequent Suzuki–Miyaura reaction furnished the target conjugated materials comprising small organic molecules. The electron-deficient dibenzothiophene-S,S-dioxide core was obtained in quantitative yield. UV-Vis absorption studies indicated changes in the positions of the peak maxima upon increasing the conjugation length. Electrochemical and theoretical investigations of selected synthesized materials are also included.

Graphical abstract: Conjugated small organic molecules: synthesis and characterization of 4-arylpyrazole-decorated dibenzothiophenes
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