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Pyrrolo[2,3‑d:5,4‑d′]bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-Ring Bithiophenes

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journal contribution
posted on 29.12.2017, 21:29 by Eric J. Uzelac, Casey B. McCausland, Seth C. Rasmussen
New synthetic methods have been developed for the preparation of 4-alkyl- and 4-aryl-pyrrolo­[2,3-d:5,4-d′]­bisthiazole (PBTz) building blocks from 2,4-thiazolidinedione. The resulting PBTz products have been fully characterized via structural, electronic, and optical methods, thus allowing full comparison to the previously reported dithieno­[3,2-b:2′,3′-d]­pyrrole (DTP) analogues. Such comparisons then allow a detailed discussion of the relative electronic effects of the various methods utilized to tune the properties of the parent DTP building block.