Control of the Helical Chirality of Enantiopure Sulfinyl ( Z )‐Azobenzene‐Based Photoswitches | Zendy

Núñez Irene | Zendy; Merino Estíbaliz | Zendy; Lecea Mercedes | Zendy; Pieraccini Silvia | Zendy; Spada Gian Piero | Zendy; Rosini Carlo | Zendy; Mazzeo Giuseppe | Zendy; Ribagorda María | Zendy; Carreño M. Carmen | Zendy

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Control of the Helical Chirality of Enantiopure Sulfinyl ( Z )‐Azobenzene‐Based Photoswitches

Author(s) -

Núñez Irene,

Merino Estíbaliz,

Lecea Mercedes,

Pieraccini Silvia,

Spada Gian Piero,

Rosini Carlo,

Mazzeo Giuseppe,

Ribagorda María,

Carreño M. Carmen

Publication year - 2013

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201203243

Subject(s) - enantiopure drug , azobenzene , photoisomerization , helicity , chirality (physics) , photoswitch , chemistry , photochemistry , molecular switch , isomerization , sulfoxide , irradiation , stereochemistry , crystallography , physics , enantioselective synthesis , molecule , organic chemistry , quantum mechanics , catalysis , chiral symmetry breaking , quark , nambu–jona lasinio model

A new class of enantiopure ortho , ortho ‐disubstituted azobenzene photoswitches has been synthesized from ( S )‐2‐( p ‐tolylsulfinyl)benzoquinone and arylhydrazines. The sulfoxide acts as a unidirectional controller of the helical chirality that arises in the Z isomer after photoisomerization. Highly congested E ‐azobenzenes 5 c showed two atropisomeric diastereoconformers in the solid state that converged upon irradiation into a unique Z isomer with defined helicity ( M ), as evident in the X‐ray structure. The chiroptical properties of this three‐state enantiopure switch can be externally tuned both photochemically and/or thermally. Theoretical CD spectra calculated by using time‐dependent DFT methods support the existence of two atropoisomeric E isomers and only one Z isomer with ( M ) helicity. Complementary to the classical azobenzene‐based switches, the photoswiching event is promoted under green/blue light and do not occur under UV irradiation.

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