Improving the property-function tuning range of thiophene materials via facile synthesis of oligo/polythiophene-s-oxides and mixed voligo/polythiophene-s-oxides/oligo/polythiophene-s,s-dioxides

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Abstract

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.

Autore Pugliese

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  • Di Maria F.; Zangoli M.; Palamá I.E.; Fabiano E.; Zanelli A.; Monari M.; Perinot A.; Caironi M.; Maiorano V.; Maggiore A.; Pugliese M.; Salatelli E.; Gigli G.; Viola I.; Barbarella G.

Titolo volume/Rivista

Advanced functional materials

Anno di pubblicazione

2016

ISSN

1616-301X

ISBN

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Numero di citazioni Wos

Nessuna citazione

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Settori ERC

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Codici ASJC

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