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Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy

Mogens Brøndsted Nielsen 1
Mogens Brøndsted Nielsen
, 
Nicolai Ree 1
Nicolai Ree
, 
Kurt V Mikkelsen 1
Kurt V Mikkelsen
, 
Martina Cacciarini 2
Martina Cacciarini
1 Department of Chemistry, University of Copenhagen, Denmark
2 Department of Chemistry, University of Florence, Italy
10.1070/RCR4944
Published 30 November 2019
Review , RCR4944, Volume 89, Issue 5, 573-586
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Nielsen M. B. et al. Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy // Russian Chemical Reviews. 2019. Vol. 89. No. 5. pp. 573-586.
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Nielsen M. B., Ree N., Mikkelsen K. V., Cacciarini M. Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy // Russian Chemical Reviews. 2019. Vol. 89. No. 5. pp. 573-586.
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TY - JOUR
DO - 10.1070/RCR4944
UR - https://rcr.colab.ws/publications/10.1070/RCR4944
TI - Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy
T2 - Russian Chemical Reviews
AU - Nielsen, Mogens Brøndsted
AU - Ree, Nicolai
AU - Mikkelsen, Kurt V
AU - Cacciarini, Martina
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 573-586
IS - 5
VL - 89
ER -
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@article{2019_Nielsen,
author = {Mogens Brøndsted Nielsen and Nicolai Ree and Kurt V Mikkelsen and Martina Cacciarini},
title = {Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4944},
number = {5},
pages = {573--586},
doi = {10.1070/RCR4944}
}
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Nielsen, Mogens Brøndsted, et al. “Tuning the dihydroazulene -- vinylheptafulvene couple for storage of solar energy.” Russian Chemical Reviews, vol. 89, no. 5, Nov. 2019, pp. 573-586. https://rcr.colab.ws/publications/10.1070/RCR4944.
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Keywords

dihydroazulene
electrocyclic reactions
energy storage
macrocycles
multiphotochromes
photochromism
thermoswitch
vinylheptafulvene

Abstract

Dihydroazulene (DHA) is a molecular photoswitch that undergoes a ring-opening reaction upon irradiation to form a vinylheptafulvene (VHF) photoisomer. This VHF isomer will in time thermally return to the DHA isomer. As the isomerization is photo-induced only in one direction, the DHA--VHF couple has attracted interest as a molecular solar thermal energy storage device (MOST system). In this author review, we cover our systematic efforts to optimize the DHA--VHF couple for this purpose, with challenges being to achieve sufficiently high energy densities, to cover broad absorptions including the visible region, and to control the energy-releasing VHF-to-DHA back-reaction. By a combination of computations and experiments, we review the consequences of various structural modifications of the system (structure--property relationships), including the influence of donor-acceptor substitution at specific positions, benzannulations, and incorporation into macrocyclic structures. Synthetic protocols to reach the various modifications will also be discussed. The bibliography includes 60 references.

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