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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
Author(s) -
Di Maria Francesca,
Zangoli Mattia,
Palamá Ilaria Elena,
Fabiano Eduardo,
Zanelli Alberto,
Monari Magda,
Perinot Andrea,
Caironi Mario,
Maiorano Vincenzo,
Maggiore Antonio,
Pugliese Marco,
Salatelli Elisabetta,
Gigli Giuseppe,
Viola Ilenia,
Barbarella Giovanna
Publication year - 2016
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201602996
Subject(s) - polythiophene , thiophene , materials science , supramolecular chemistry , polymer chemistry , conductive polymer , nanotechnology , combinatorial chemistry , polymer , organic chemistry , molecule , chemistry , composite material
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.