Poly(p-phenylene ethynylene) Incorporating Sterically Enshrouding m-Terphenyl Oxacyclophane Canopies

Authors

  • Brad P. Morgan,

    1. Department of Chemistry and Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University, Clemson, SC 29634, USA
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  • Robert J. Gilliard Jr.,

    1. Department of Chemistry and Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University, Clemson, SC 29634, USA
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  • Rahul S. Loungani,

    1. Department of Chemistry and Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University, Clemson, SC 29634, USA
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  • Rhett C. Smith

    Corresponding author
    1. Department of Chemistry and Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University, Clemson, SC 29634, USA
    • Department of Chemistry and Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University, Clemson, SC 29634, USA.
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Abstract

A sterically encumbered m-terphenyl oxacyclophane substituted with two aryl iodide substituents has been prepared as a versatile monomer for the preparation of π-conjugated polymers. The monomer has been used to prepare a poly(p-phenylene ethynylene) derivative (P1) incorporating oxacyclophane units as canopies that shield one side of the π-system from inter-chain interactions. The photophysical properties of P1 in dilute solution compare well to those of a poly(p-phenylene ethynylene) derivative (P2) that lacks the canopy. The presence of the steric canopy leads to a diminished inter-chain interaction in the solid state and enhances the kinetic response of P1 to vapors of nitro-organics such as TNT, presumably by increasing the permeability of P1 to these analytes over that of P2.

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