4.8 Article

Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of Oligo/Polythiophene-S-Oxides and Mixed Oligo/Polythiophene-S-Oxides/Oligo/Polythiophene-S,S-Dioxides

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ADVANCED FUNCTIONAL MATERIALS
卷 26, 期 38, 页码 6970-6984

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/adfm.201602996

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  1. project Molecular Nanotechnologies for Human Health and Environment [PON RC 611 2007-2013, PON02_00563_3316357]

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A platform is described for the first time for the facile synthesis of oligo-and polythiophene-S-oxides and the corresponding -S,S-dioxides in short times, mild conditions, high yields. Employing ultrasound assistance, brominated thiophenes are selectively mono-or dioxygenated at room temperature. These building blocks are then combined with metalated thiophenes via microwave-assisted cross-coupling reactions through a Lego-like strategy to afford unprecedented oligo/polythiophene-S-oxides and mixed -S-oxides/-S,S-dioxides. It is demonstrated that depending on the number, type, and sequence alternation of nonoxygenated, monooxygenated, and dioxygenated thiophene units a very wide property-function tuning can be achieved spanning from frontier orbital energies and energy gaps, to charge transport characteristics and supramolecular H-bonding interactions with specific proteins inside live cells.

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