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  Photochromic Torsional Switch (PTS): a light-driven actuator for the dynamic tuning of π-conjugation extension

Maciejewski, J., Sobczuk, A., Claveau, A., Nicolai, A., Petraglia, R., Cervini, L., et al. (2017). Photochromic Torsional Switch (PTS): a light-driven actuator for the dynamic tuning of π-conjugation extension. Chemical Science, 8, 361-365. doi:10.1039/C6SC03196J.

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 Creators:
Maciejewski, Jan1, Author
Sobczuk, Adam1, Author
Claveau, Alexis1, Author
Nicolai, Adrien2, Author
Petraglia, Riccardo2, Author
Cervini, Luca1, Author
Baudat, Emilie3, Author
Miéville, Pascal3, Author
Fazzi, Daniele4, Author              
Corminboeuf, Clemence2, Author
Sforazzini, Guiseppe1, Author
Affiliations:
1Laboratory of Macromolecular and Organic Materials, Institute of Material Science and Engineering, Ecole Polytechnique Federale de Lausanne (EPFL), 1015 Lausanne, Switzerland , ou_persistent22              
2Laboratory for Computational Molecular Design, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne (EPFL), 1015 Lausanne, Switzerland, ou_persistent22              
3Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland, ou_persistent22              
4Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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 Abstract: 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.

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 Dates: 2016-07-192016-08-152017-07-01
 Publication Status: Published online
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/C6SC03196J
 Degree: -

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Title: Chemical Science
  Other : Chem. Sci.
Source Genre: Journal
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Publ. Info: Cambridge, UK : Royal Society of Chemistry
Pages: - Volume / Issue: 8 Sequence Number: - Start / End Page: 361 - 365 Identifier: ISSN: 2041-6520
CoNE: https://pure.mpg.de/cone/journals/resource/2041-6520