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

Here we present a molecular architecture that can reversibly change the geometric conformation of its π-system backbone irradiation with two different wavelengths. The proposed 'molecular actuator' consists of a photoswitchable azobenzene orthogonally connected to a π-conjugated bithiophen...

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Veröffentlicht in:Chemical science (Cambridge) 2017-01, Vol.8 (1), p.361-365
Hauptverfasser: Maciejewski, Jan, Sobczuk, Adam, Claveau, Alexis, Nicolai, Adrien, Petraglia, Riccardo, Cervini, Luca, Baudat, Emilie, Miéville, Pascal, Fazzi, Daniele, Corminboeuf, Clemence, Sforazzini, Giuseppe
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Sprache:eng
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Zusammenfassung:Here we present a molecular architecture that can reversibly change the geometric conformation of its π-system backbone 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 azobenzene moiety isomerizes to its 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 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 computations. The proposed molecular design could be envisaged as a π-conjugation modulator, which has potential to be incorporated into extended linear π-systems, the terminal α-thiophene positions, and used to tune their optical and electronic properties.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc03196j