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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
A New Solution to an Old Problem: Synthesis of Unsubstituted Poly(para-phenylene)
Ali Abdulkarim1,2,3, Felix Hinkel2,4, Daniel Jänsch1,2
1InnovationLab , Speyererstr. 4, 69115 Heidelberg, Germany.
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.
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