Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles

  1. Sandra OlssonORCID Logo,
  2. Óscar Benito PérezORCID Logo,
  3. Magnus Blom and
  4. Adolf GogollORCID Logo

Submitting author affiliation: Uppsala University, Uppsala, Sweden

Beilstein Arch. 2019, 201930. https://doi.org/10.3762/bxiv.2019.30.v1

Published 28 May 2019

  • Preprint


A series of stiff stilbene macrocycles have been studied to investigate the possible impact of macrocycle ring size on their photo-dynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. In general, it is indicated that addition of even a flexible chain to the stiff stilbene unit may significantly affect  its photochemical properties and increase the photostability of the resulting macrocycle.

Keywords: stiff stilbene; photo-switch; ring-strain; photostability; DFT; molecular mechanics;

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Olsson, S.; Benito Pérez, Ó.; Blom, M.; Gogoll, A. Beilstein Arch. 2019, 201930. doi:10.3762/bxiv.2019.30.v1

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