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

Yurachat Janpatompong, Andrew M. Spring, Venukrishnan Komanduri, Raja U. Khan, Michael L. Turner

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)10854-10864
Number of pages11
JournalMacromolecules
Volume55
Issue number24
DOIs
Publication statusPublished - Dec 27 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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