Molecular Tuning in Diaryl-Capped Pyrrolo[2,3- d:5,4- d']bisthiazoles: Effects of Terminal Aryl Unit and Comparison to Dithieno[3,2- b:2',3'- d]pyrrole Analogues

Eric J Uzelac; Irene Badía-Domínguez; Spencer J Gilman; M Carmen Ruiz Delgado; Seth C Rasmussen

doi:10.3390/molecules27196638

Molecular Tuning in Diaryl-Capped Pyrrolo[2,3- d:5,4- d']bisthiazoles: Effects of Terminal Aryl Unit and Comparison to Dithieno[3,2- b:2',3'- d]pyrrole Analogues

Molecules. 2022 Oct 6;27(19):6638. doi: 10.3390/molecules27196638.

Authors

Eric J Uzelac¹, Irene Badía-Domínguez², Spencer J Gilman¹, M Carmen Ruiz Delgado², Seth C Rasmussen¹

Affiliations

¹ Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108-6050, USA.
² Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, 29071 Málaga, Spain.

Abstract

A series of six conjugated oligomers consisting of a central pyrrolo[2,3-d:5,4-d']bisthiazole (PBTz) end-capped with either thienyl, furyl, or phenyl groups have been prepared from N-alkyl-and N-aryl-pyrrolo[2,3-d:5,4-d']bisthiazoles via Stille and Negishi cross-coupling. The full oligomeric series was thoroughly investigated via photophysical and electrochemical studies, in parallel with density functional theory (DFT) calculations, in order to correlate the cumulative effects of both aryl end-groups and N-functionalization on the resulting optical and electronic properties. Through comparison with the analogous dithieno[3,2-b:2',3'-d]pyrrole (DTP) materials, the effect of replacing DTP with PBTz on the material HOMO energy and visible light absorption is quantified.

Keywords: conjugated materials; dithieno[3,2-b:2’,3’-d]pyrrole; fused-ring heterocycles; pyrrolo[2,3-d:5,4-d′]bisthiazole; structure–function relationships.

Abstract

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