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Issue 14, 2020
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Controlled synthesis of unsubstituted high molecular weight poly(para-phenylene) via Suzuki polycondensation-thermal aromatization methodology

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Abstract

Suzuki polycondensation-thermal aromatization methodology was developed as a versatile new route to structurally regular, unsubstituted high molecular weight poly(para-phenylene) (PPP). The utility of this methodology was demonstrated by synthesizing PPP from both cis- and trans-precursor prepolymers 1a–b. The structure of precursor prepolymers containing exclusively 1,4-repeating units with the hydroxyphenyl group at the chain end was determined by two-dimensional NMR spectroscopy. Pyrolysis of trans-poly(para-phenylene) precursor 1b resulted in complete aromatization to PPP containing an average of 110 phenylene units in the polymer chain. The thermal conversion of precursor polymers to polyphenylene is a straightforward process leading to pristine PPP without significant chain degradation as confirmed by solid-state NMR and TGA analysis. The characterization of PPP by solid-state NMR, UV-vis absorption, fluorescence emission and IR spectroscopy, TGA, and conductivity measurements exhibits significant features for electronic and photoelectronic application, such as broadened absorption, high thermal stability, and typical conducting properties.

Graphical abstract: Controlled synthesis of unsubstituted high molecular weight poly(para-phenylene) via Suzuki polycondensation-thermal aromatization methodology

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Supplementary files

Article information


Submitted
01 Jan 2020
Accepted
03 Mar 2020
First published
07 Mar 2020

Polym. Chem., 2020,11, 2550-2558
Article type
Paper

Controlled synthesis of unsubstituted high molecular weight poly(para-phenylene) via Suzuki polycondensation-thermal aromatization methodology

D. Pavlović and S. Cohen, Polym. Chem., 2020, 11, 2550
DOI: 10.1039/D0PY00001A

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