Thioalkyl- and Sulfone-Substituted Poly(p-Phenylene Vinylene)s

30 October 2018, Version 1

Abstract

Poly(p-phenylene vinylene)s (PPVs) have been studied for decades, but research on this interesting class of conjugated polymers is far from being completed. New applications like in bioimaging keep emerging and even simple structural variations are still waiting to be explored. Surprisingly, not even dithioalkyl-substituted PPVs (S-PPVs) have been reported in the peer-reviewed literature, although the corresponding dialkoxy-substituted PPVs (O-PPVs) like MEH-PPV or MDMO-PPV are most frequently used and although thioalkyl substituents can improve the material properties significantly. We herein report the development of a highly efficient, scalable two-step synthesis of Gilch monomers for S-PPVs starting from low-cost 1,4-diiodobenzene. A low-temperature polymerization protocol has been developed for these monomers, affording high-molecular weight S-PPVs in excellent yields. The thermal, electrochemical, and photophysical properties of S-PPVs are reported to highlight the potential of these polymers. Furthermore, treatment with dimethyldioxirane is demonstrated to result in rapid conversion into sulfone-substituted PPVs (SO2-PPVs), introducing a route to high-molecular weight SO2-PPVs with exceptional stability and solid-state photoluminescence quantum yields of up to 0.46.

Keywords

Poly(p-phenylene vinylene)s
Conjugated polymers
Conductive polymers
Organic Electronics
Thioalkyl substituents
Sulfones
Gilch polymerization
Low temperature polymerization
Microwave-assisted synthesis
Bromomethylation
Post-polymerization modification
Dimethyldioxirane
Photoluminescence
Thin-films

Supplementary materials

Title
Description
Actions
Title
S-PPV Preprint Supporting Information
Description
Actions
Title
4a to 5a
Description
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Title
4b to 5b
Description
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