Photochemical and Thermal Isomerization Processes of a Chiral Auxiliary Based Donor–Acceptor Substituted Chiroptical Molecular Switch: Convergent Synthesis, Improved Resolution and Switching Properties | Zendy

van Delden Richard A. | Zendy; Hurenkamp Johannes H. | Zendy; Feringa Ben L. | Zendy

Premium

Photochemical and Thermal Isomerization Processes of a Chiral Auxiliary Based Donor–Acceptor Substituted Chiroptical Molecular Switch: Convergent Synthesis, Improved Resolution and Switching Properties

Author(s) -

van Delden Richard A.,

Hurenkamp Johannes H.,

Feringa Ben L.

Publication year - 2003

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.200204660

Subject(s) - stereocenter , pyrrolidine , chemistry , molecular switch , photochemistry , steric effects , chiral auxiliary , isomerization , diastereomer , circular dichroism , chirality (physics) , absolute configuration , stereochemistry , enantioselective synthesis , molecule , organic chemistry , physics , catalysis , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark

A new type of chiroptical molecular switch is presented where irradiation employing different wavelengths of light induces a reversible helix inversion of a sterically overcrowded alkene bearing a second chiral entity in the form of a stereogenic center present in a pyrrolidine unit. The additional stereogenic center in the chiral auxiliary group has a distinct influence on the switching selectivity of this system and greatly facilitates the resolution of the different diastereoisomers, which is a considerable improvement compared with previously reported systems. In addition, the pyrrolidine stereogenic center causes small energetic differences between the various states of the switch system resulting in a small but significant directional preference in the helix inversion steps.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research