Direct evidence for hula twist and single-bond rotation photoproducts

Aaron Gerwien, Monika Schildhauer, Stefan Thumser, Peter Mayer and Henry Dube ()
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Aaron Gerwien: Ludwig-Maximilians-Universität München and Munich Center for Integrated Protein Science CIPSM
Monika Schildhauer: Ludwig-Maximilians-Universität München and Munich Center for Integrated Protein Science CIPSM
Stefan Thumser: Ludwig-Maximilians-Universität München and Munich Center for Integrated Protein Science CIPSM
Peter Mayer: Ludwig-Maximilians-Universität München and Munich Center for Integrated Protein Science CIPSM
Henry Dube: Ludwig-Maximilians-Universität München and Munich Center for Integrated Protein Science CIPSM

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Photoisomerization reactions are quintessential processes driving molecular machines and motors, govern smart materials, catalytic processes, and photopharmacology, and lie at the heart of vision, phototaxis, or vitamin production. Despite this plethora of applications fundamental photoisomerization mechanisms are not well understood at present. The famous hula-twist motion—a coupled single and double-bond rotation—was proposed to explain proficient photoswitching in restricted environments but fast thermal follow-up reactions hamper identification of primary photo products. Herein we describe an asymmetric chromophore possessing four geometrically distinct diastereomeric states that do not interconvert thermally and can be crystallized separately. Employing this molecular setup direct and unequivocal evidence for the hula-twist photoreaction and for photoinduced single-bond rotation is obtained. The influences of the surrounding medium and temperature are quantified and used to favor unusual photoreactions. Based on our findings molecular engineers will be able to implement photo control of complex molecular motions more consciously.

Date: 2018
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DOI: 10.1038/s41467-018-04928-9

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