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Molecules 2018, 23(9), 2279; https://doi.org/10.3390/molecules23092279

Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles

Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108-6050, USA
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Received: 14 August 2018 / Revised: 30 August 2018 / Accepted: 3 September 2018 / Published: 6 September 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

The synthesis of four N-functionalized bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles (BBTPs) is reported in order to provide a more detailed characterization of these fused-ring units, as well as increase the scope of known BBTP units available for application to conjugated materials. The optical, electronic, and structural properties of the resulting BBTP units have been compared to the parent N-alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrroles (DTPs), as well as their corresponding 2,6-diphenyl derivatives, in order to fully quantify the relative electronic effects resulting from benzannulation of the parent DTP building block. Such comparative analysis reveals that benzannulation results in a red-shifted absorbance, but to a lesser extent than simple phenyl-capping of the DTP. More surprising is that benzannulation results in stabilization of the BBTP HOMO, compared to the destabilization normally observed with extending the conjugation length of the backbone. View Full-Text
Keywords: fused-ring thiophenes; heteroacenes; dithieno[3,2-b:2′,3′-d]pyrroles; benzannulation; structure-function relationships fused-ring thiophenes; heteroacenes; dithieno[3,2-b:2′,3′-d]pyrroles; benzannulation; structure-function relationships
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wolfe, R.M.W.; Culver, E.W.; Rasmussen, S.C. Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles. Molecules 2018, 23, 2279.

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