Synthesis and Properties of N-Arylpyrrole-Functionalized Poly(1-hexene-alt-CO)
2018
Samples, Evan M. | Schuck, Jeremy M. | Joshi, Padmanabh B. | Willets, Katherine A. | Dobereiner, Graham E.
The 1,4-polyketone derived from 1-hexene and carbon monoxide, poly(1-hexene-alt-CO) (1), can undergo Paal–Knorr cyclization with substituted anilines to yield N-pyrrole-functionalized polyketones. A variety of pendant functionalities are introduced to 1, including azobenzene (6) and triarylamines (5a–e). The extent of incorporation depends on the nucleophilicity of the parent aniline. Polymer 6 exhibits a UV-induced trans → cis photoisomerization and has lower rates of photoinduced decomposition relative to parent 1. Triarylamine-containing polymers 5a–e are redox-active, forming optically active radical cations upon chemical oxidation. Compared with model N-arylpyrrole compounds 9a–e, polymers 5a–e demonstrate hypsochromic shifts in UV–vis absorptions and exhibit features between +0.5 and +1.2 V (vs Ag/AgCl) in solution-phase differential pulse voltammetry.
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