Journal article
Photochromic Torsional Switch (PTS): a light-driven actuator for the dynamic tuning of π-conjugation extension.
- Maciejewski J Laboratory of Macromolecular and Organic Materials , Institute of Material Science and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: giuseppe.sforazzini@epfl.ch.
- Sobczuk A Laboratory of Macromolecular and Organic Materials , Institute of Material Science and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: giuseppe.sforazzini@epfl.ch.
- Claveau A Laboratory of Macromolecular and Organic Materials , Institute of Material Science and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: giuseppe.sforazzini@epfl.ch.
- Nicolai A Laboratory for Computational Molecular Design , Institute of Chemical Sciences and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland.
- Petraglia R Laboratory for Computational Molecular Design , Institute of Chemical Sciences and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland.
- Cervini L Laboratory of Macromolecular and Organic Materials , Institute of Material Science and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: giuseppe.sforazzini@epfl.ch.
- Baudat E Institute of Chemical Sciences and Engineering , École Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland.
- Miéville P Institute of Chemical Sciences and Engineering , École Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland.
- Fazzi D Department of Theoretical Chemistry , Max-Planck-Institut für Kohlenforschung , D-45470 Mülheim an der Ruhr , Germany.
- Corminboeuf C Laboratory for Computational Molecular Design , Institute of Chemical Sciences and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland.
- Sforazzini G Laboratory of Macromolecular and Organic Materials , Institute of Material Science and Engineering , Ecole Polytechnique Federale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: giuseppe.sforazzini@epfl.ch.
- 2017-04-29
Published in:
- Chemical science. - 2017
English
Here we present a molecular architecture that can reversibly change the geometric conformation of its π-system backbone via irradiation with two different wavelengths. The proposed 'molecular actuator' consists of a photoswitchable azobenzene orthogonally connected to a π-conjugated bithiophene by both direct and aliphatic linker-assisted bonding. Upon exposure to 350 nm light, the trans azobenzene moiety isomerizes to its cis form, causing the bithiophene to assume a semiplanar anti conformation (extended π-conjugation). Exposure to 254 nm light promotes the isomerization of the azobenzene unit back to its initial extended trans conformation, thus forcing the bithiophene fragment to twist out of coplanarity (restricted π-conjugation). The molecular conformation of the bithiophene was characterized using steady-state UV-vis and nuclear magnetic resonance spectroscopy, as well as ab initio computations. The proposed molecular design could be envisaged as a π-conjugation modulator, which has potential to be incorporated into extended linear π-systems, i.e. via the terminal α-thiophene positions, and used to tune their optical and electronic properties.
- Language
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- English
- Open access status
- gold
- Identifiers
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- DOI 10.1039/c6sc03196j
- PMID 28451180
- Persistent URL
- https://folia.unifr.ch/global/documents/204393
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