Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 12, Pages 2845-2853Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200204660
Keywords
chirality; isomerization; molecular devices; nanotechnology; photochromism
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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.
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