Investigating the impact of regiochemistry in ester functionalized polyfurans |
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Authors: | Anthony J Varni Manami Kawakami Stephanie N Kramer Megan Rice Steven J Geib Linda A Peteanu Tomasz Kowalewski Kevin J T Noonan |
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Institution: | 1. Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania, USA;2. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, USA |
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Abstract: | In this study, the impact of ester side group regiochemistry on electronic and conformational properties of regioregular polyfurans was explored. A derivative with alternating head-to-head and tail-to-tail orientation of the side groups was synthesized and compared with its head-to-tail analogue, and these were benchmarked against the related regioregular poly(3-hexylfurans). The study revealed that alkyl ester side groups in a head-to-head orientation will create significant steric strain as compared with linear alkyl chains with identical regiochemistry. Though the head-to-head ester side groups lead to twisting along the polymer backbone, they also produce a protective effect against photodegradation in comparison with a poly(3-hexylfuran). Altogether, the work highlights how side groups can impact conformational properties and stability of polyfurans. |
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Keywords: | polyfurans regioregularity side chain engineering torsional potentials |
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