A New Solution to an Old Problem: Synthesis of Unsubstituted Poly(para-phenylene)

J Am Chem Soc. 2016 Dec 21;138(50):16208-16211. doi: 10.1021/jacs.6b10254. Epub 2016 Dec 9.

Abstract

Unsubstituted and structurally well-defined poly(para-phenylene) (PPP) has been long-desired as an organic semiconductor prototype of conjugated polymers. To date, several attempts to synthesize unsubstituted, pristine, high-molecular-weight PPP have failed. Here we solved this synthetic problem by a versatile precursor route. Suzuki polymerization of kinked disubstituted 1,4-dimethoxycyclohexadienylene monomers yielded a well-soluble, nonaromatic precursor polymer. Its solubility allowed processing by spin-coating into nanometer-thick films. Subsequent additive-free thermal treatment induced aromatization and led to exclusively para-connected, highly fluorescent PPP with a length of about 75 phenylene units.

Publication types

  • Research Support, Non-U.S. Gov't