[2.2]Paracyclophane-1,9-diene (pCpd) is an important class of monomer as it can afford poly(phenylenevinylene)s (PPV) via a controlled living polymerization method. pCpd was first reported by Cram and coworkers in 1958 and was shown in 1992 to undergo ring-opening metathesis polymerization (ROMP) with limited solubility by Thorn-Csányi <i>et al.</i> using tungsten catalysts. In the past two decades, Michael L. Turner’s group reported a more facile synthesis to pCpd and described the living ROMP using ruthenium-based catalysts. Due to the harsh reaction conditions still required to synthesize pCpds, di- or tetra- para- alkyl or alkoxy groups are the only substitution and side-chains successfully reported to date. This presentation will close this gap twofold: first introducing structurally diverse pCpds that are not just para-substituted and second developing a methodology to append functional side-chains to pCpds. With our recent advances, ROMP with diversely substituted functional pCpds has the potential to afford Pi-conjugated polymers with interesting microstructures for a wide variety of applications including as photoresponsive optoelectronic materials.

Expanding the library of [2.2]paracylophane-1,9-dienes for ROMP

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ACS Fall 2022

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