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Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple
Author(s) -
Skov Anders B.,
Petersen Johannes F.,
Elm Jonas,
Frandsen Benjamin N.,
Santella Marco,
Kilde Martin Drøhse,
Kjaergaard Henrik G.,
Mikkelsen Kurt V.,
Nielsen Mogens Brøndsted
Publication year - 2017
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201600046
Subject(s) - photochromism , photoswitch , photochemistry , cycloaddition , molecule , stereoselectivity , chemistry , irradiation , energy storage , materials science , organic chemistry , physics , catalysis , power (physics) , quantum mechanics , nuclear physics
One challenge in the development of molecular photoswitches for solar energy storage is to increase the energy of the isomer formed upon irradiation. This work focuses on how to affect the relative stabilities of the isomers of the dihydroazulene/ vinylheptafulvene (DHA/VHF) couple by combining the light‐induced DHA to VHF conversion with the loss of aromaticity. We present a synthetic procedure for benzannulation of DHA at the C7−C8 bond, with the key steps being a stereoselective Diels–Alder cycloaddition followed by an oxidation. The optical properties and switching abilities of this compound are described in a combined theoretical and experimental study. Calculations support that benzannulation serves to increase the overall energy capacity of the photoswitch by stabilizing the DHA and destabilizing the VHF.