Photochemical and thermal isomerization processes of a chiral auxiliary based donor-acceptor substituted chiroptical molecular switch: convergent synthesis,improved resolution and switching properties |
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Authors: | van Delden Richard A Hurenkamp Johannes H Feringa Ben L |
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Institution: | Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, The Netherlands. |
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Abstract: | 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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Keywords: | chirality isomerization molecular devices nanotechnology photochromism |
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