Molecular Solar Thermal Energy Storage Systems with Long Discharge Times Based on the Dihydroazulene/Vinylheptafulvene Couple

Josefine Mogensen; Oliver Christensen; Martin Drøhse Kilde; Martin Abildgaard; Lotte Metz; Anders Kadziola; Martyn Jevric; Kurt V. Mikkelsen; Mogens Brøndsted Nielsen

doi:10.1002/ejoc.201801776

Molecular Solar Thermal Energy Storage Systems with Long Discharge Times Based on the Dihydroazulene/Vinylheptafulvene Couple

Josefine Mogensen, Oliver Christensen, Martin Drøhse Kilde, Martin Abildgaard, Lotte Metz, Anders Kadziola, Martyn Jevric, Kurt V. Mikkelsen, Mogens Brøndsted Nielsen^*

^*Corresponding author for this work

5 Citations (Scopus)

Abstract

Molecular solar thermal energy storage (MOST) systems based on photochromic molecules that undergo photoisomerization to high-energy isomers are attractive for storage of solar energy in a closed-energy cycle. One challenge is to control the discharge time of the high-energy isomer. Here we show that incorporation of a strong acceptor substituent in the seven-membered ring of the dihydroazulene/vinylheptafulvene (DHA/VHF) couple increases the half-life of the energy-releasing VHF-to-DHA back-reaction from hours to more than a day in a polar solvent. For some derivatives, the absorption maximum of the photo-active DHA is also significantly redshifted, thereby better matching the solar spectrum. Synthetic protocols and kinetics studies are presented together with a computational study of the energy densities of the systems and excitation spectra. The computations show that the increased lifetime of the high-energy isomer is counter-balanced by a lower energy storage capacity in vacuo than for the parent system, but a slightly higher energy density than for the parent system in a polar solvent.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	10
Pages (from-to)	1986-1993
Number of pages	8
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201801776
Publication status	Published - 14 Mar 2019

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Molecular Solar Thermal Energy Storage Systems with Long Discharge Times Based on the Dihydroazulene/Vinylheptafulvene Couple. / Mogensen, Josefine; Christensen, Oliver; Kilde, Martin Drøhse et al.
In: European Journal of Organic Chemistry, Vol. 2019, No. 10, 14.03.2019, p. 1986-1993.

Research output: Contribution to journal › Journal article › Research › peer-review

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title = "Molecular Solar Thermal Energy Storage Systems with Long Discharge Times Based on the Dihydroazulene/Vinylheptafulvene Couple",

abstract = "Molecular solar thermal energy storage (MOST) systems based on photochromic molecules that undergo photoisomerization to high-energy isomers are attractive for storage of solar energy in a closed-energy cycle. One challenge is to control the discharge time of the high-energy isomer. Here we show that incorporation of a strong acceptor substituent in the seven-membered ring of the dihydroazulene/vinylheptafulvene (DHA/VHF) couple increases the half-life of the energy-releasing VHF-to-DHA back-reaction from hours to more than a day in a polar solvent. For some derivatives, the absorption maximum of the photo-active DHA is also significantly redshifted, thereby better matching the solar spectrum. Synthetic protocols and kinetics studies are presented together with a computational study of the energy densities of the systems and excitation spectra. The computations show that the increased lifetime of the high-energy isomer is counter-balanced by a lower energy storage capacity in vacuo than for the parent system, but a slightly higher energy density than for the parent system in a polar solvent.",

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AU - Mogensen, Josefine

AU - Christensen, Oliver

AU - Kilde, Martin Drøhse

AU - Abildgaard, Martin

AU - Metz, Lotte

AU - Kadziola, Anders

AU - Jevric, Martyn

AU - Mikkelsen, Kurt V.

AU - Nielsen, Mogens Brøndsted

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N2 - Molecular solar thermal energy storage (MOST) systems based on photochromic molecules that undergo photoisomerization to high-energy isomers are attractive for storage of solar energy in a closed-energy cycle. One challenge is to control the discharge time of the high-energy isomer. Here we show that incorporation of a strong acceptor substituent in the seven-membered ring of the dihydroazulene/vinylheptafulvene (DHA/VHF) couple increases the half-life of the energy-releasing VHF-to-DHA back-reaction from hours to more than a day in a polar solvent. For some derivatives, the absorption maximum of the photo-active DHA is also significantly redshifted, thereby better matching the solar spectrum. Synthetic protocols and kinetics studies are presented together with a computational study of the energy densities of the systems and excitation spectra. The computations show that the increased lifetime of the high-energy isomer is counter-balanced by a lower energy storage capacity in vacuo than for the parent system, but a slightly higher energy density than for the parent system in a polar solvent.

AB - Molecular solar thermal energy storage (MOST) systems based on photochromic molecules that undergo photoisomerization to high-energy isomers are attractive for storage of solar energy in a closed-energy cycle. One challenge is to control the discharge time of the high-energy isomer. Here we show that incorporation of a strong acceptor substituent in the seven-membered ring of the dihydroazulene/vinylheptafulvene (DHA/VHF) couple increases the half-life of the energy-releasing VHF-to-DHA back-reaction from hours to more than a day in a polar solvent. For some derivatives, the absorption maximum of the photo-active DHA is also significantly redshifted, thereby better matching the solar spectrum. Synthetic protocols and kinetics studies are presented together with a computational study of the energy densities of the systems and excitation spectra. The computations show that the increased lifetime of the high-energy isomer is counter-balanced by a lower energy storage capacity in vacuo than for the parent system, but a slightly higher energy density than for the parent system in a polar solvent.

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DO - 10.1002/ejoc.201801776

M3 - Journal article

SN - 1434-193X

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

Molecular Solar Thermal Energy Storage Systems with Long Discharge Times Based on the Dihydroazulene/Vinylheptafulvene Couple

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