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Synthesis and Ring-Opening Metathesis Polymerization of -Dialkoxy Paracyclophanedienes

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Journal Macromolecules
Date 2023 Jan 2
PMID 36590370
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Abstract

The highly strained -diethylhexyloxy [2.2]paracyclophane-1,9-diene () can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement. This paracyclophanediene undergoes ring-opening metathesis polymerization to give well-defined 2,3-dialkoxyphenylenevinylene polymers with an alternating / alkene stereochemistry and controllable molecular weight. Fully conjugated block copolymers with electron-rich and electron-deficient phenylene vinylene polymer segments can be prepared by sequential monomer additions. These polymers can be readily isomerized to the all- stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.

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