Synthesis and Ring-Opening Metathesis Polymerization of o‑Dialkoxy Paracyclophanedienes

The highly strained ortho-diethylhexyloxy [2.2]­paracyclophane-1,9-diene (M1) 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-dialk...

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Published inMacromolecules Vol. 55; no. 24; pp. 10854 - 10864
Main Authors Janpatompong, Yurachat, Spring, Andrew M., Komanduri, Venukrishnan, Khan, Raja U., Turner, Michael L.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 27.12.2022
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Summary:The highly strained ortho-diethylhexyloxy [2.2]­paracyclophane-1,9-diene (M1) 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 cis/trans 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-trans stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.
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ISSN:0024-9297
1520-5835
DOI:10.1021/acs.macromol.2c02111