Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/ Vinylheptafulvene Couple

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DOI

  • Anders B. Skov, University of Copenhagen
  • ,
  • Johannes F. Petersen, University of Copenhagen
  • ,
  • Jonas Elm
  • Benjamin N. Frandsen, University of Copenhagen
  • ,
  • Marco Santella, University of Copenhagen
  • ,
  • Martin Drohse Kilde, University of Copenhagen
  • ,
  • Henrik G. Kjaergaard, University of Copenhagen
  • ,
  • Kurt V. Mikkelsen, University of Copenhagen
  • ,
  • Mogens Brondsted Nielsen

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.

Original languageEnglish
JournalChemPhotoChem
Volume1
Issue5
Pages (from-to)206-212
Number of pages7
ISSN2367-0932
DOIs
Publication statusPublished - May 2017
Externally publishedYes

    Research areas

  • aromaticity, cycloaddition, electrocyclic reactions, fused-ring systems, photochromism, DERIVATIVES, SYSTEM, (FULVALENE)TETRACARBONYLDIRUTHENIUM, PHOTOSWITCHES, CAPACITY, RING

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