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 |
| |
| Authors: | Francesca Di Maria Mattia Zangoli Ilaria Elena Palamá Eduardo Fabiano Alberto Zanelli Magda Monari Andrea Perinot Mario Caironi Vincenzo Maiorano Antonio Maggiore Marco Pugliese Elisabetta Salatelli Giuseppe Gigli Ilenia Viola Giovanna Barbarella |
| |
| Affiliation: | 1. Dpt. of Mathematics and Physics Ennio De Giorgi, University of Salento and CNR‐ISOF, Bologna, Italy;2. CNR‐ISOF and Mediteknology, Consiglio Nazionale Richerche, Bologna, Italy;3. CNR‐NANOTEC‐Institute of Nanotechnology c/o Campus Ecotekne, University of Salento, Lecce, Italy;4. CNR‐NANO (ECMT) and Center for Biomolecular, Nanotechnologies@UNILE(IIT), Lecce, Italy;5. Dpt. of Chemistry Giacomo Ciamician, University of Bologna, Bologna, Italy;6. Dpt. of Physics, Politecnico di Milano, Milano, Italy;7. Center for Nano Science and Technology@PoliMi, Istituto Italiano di Tecnologia, Milano, Italy;8. Dpt. of Mathematics and Physics Ennio De Giorgi, University of Salento, Lecce, Italy;9. Echolight srl, R&D Dpt, Campus Ecotekne, Lecce, Italy;10. Dpt. of Industrial Chemistry Toso Montanari, University of Bologna, Bologna, Italy;11. CNR‐NANOTEC, Institute of Nanotechnology and Dept. of Mathematics and Physics Ennio De Giorgi, University of Salento, Lecce, Italy;12. CNR‐NANOTEC and Dpt. of Physics, Sapienza University, Rome, Italy |
| |
| 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. |
| |
| Keywords: | oligothiophene‐S‐oxides polythiophene‐S‐oxides thiophene materials synthesis thiophene sulfur chemoselective oxidation live cells |
|
|
