Norbornadiene-dihydroazulene conjugates

Organic & Biomolecular Chemistry
Martin Drøhse KildeMogens Brøndsted Nielsen

Abstract

The introduction of various photochromic units into the same molecule is an attractive approach for the development of novel molecular solar thermal (MOST) energy storage systems. Here, we present the synthesis and characterisation of a series of covalently linked norbornadiene/dihydroazulene (NBD/DHA) conjugates, using the Sonogashira coupling as the key synthetic step. Generation of the fully photoisomerized quadricyclane/vinylheptafulvene (QC/VHF) isomer was found to depend strongly on how the two units are connected - by linear conjugation (a para-phenylene bridge) or cross-conjugation (a meta-phenylene bridge) or by linking to the five- or seven-membered ring of DHA - as well as on the electronic character of another substituent group on the NBD unit. When the QC-VHF system could be reached, the QC-to-NBD back-reaction occurred faster than the VHF-to-DHA back-reaction, while the latter could be promoted simply by the addition of Cu(i) ions. The absence or presence of Cu(i) can thus be used to control whether heat releases should occur on different or identical time scales. The experimental findings were rationalized in a computational study by comparing natural transition orbitals (NTOs). Moreover, the calculations reveale...Continue Reading

References

Sep 22, 2005·Journal of Computational Chemistry·G R Kneller
Jun 18, 2010·Journal of the American Chemical Society·Søren Lindbaek BromanMogens Brøndsted Nielsen
Apr 19, 2011·Chemical Communications : Chem Comm·Christian Richard ParkerMogens Brøndsted Nielsen
Jun 22, 2011·Nano Letters·Alexie M Kolpak, Jeffrey C Grossman
Oct 11, 2011·Journal of Cheminformatics·Noel M O'BoyleGeoffrey R Hutchison
Sep 19, 2012·The Journal of Organic Chemistry·Marco SantellaMogens Brøndsted Nielsen
Dec 10, 2013·The Journal of Organic Chemistry·Søren Lindbæk BromanMogens Brøndsted Nielsen
Jan 9, 2015·The Journal of Physical Chemistry. a·Stine T OlsenKurt V Mikkelsen
Jan 16, 2015·Chemistry : a European Journal·Anne U PetersenMogens Brøndsted Nielsen
Mar 21, 2013·The Journal of Physical Chemistry Letters·E Durgun, Jeffrey C Grossman
Mar 12, 2016·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Mikael J KuismaPaul Erhart
Mar 22, 2016·Physical Chemistry Chemical Physics : PCCP·Chavdar SlavovJosef Wachtveitl
Jun 3, 2016·Chemistry : a European Journal·Alexandru VlasceanuMogens Broendsted Nielsen
Aug 6, 2016·Chemistry : a European Journal·Maria QuantKasper Moth-Poulsen
Feb 25, 2017·ACS Applied Materials & Interfaces·Eugene N ChoJeffrey C Grossman
May 17, 2017·Chemical Communications : Chem Comm·Martina CacciariniMogens Brøndsted Nielsen
Aug 31, 2017·The Journal of Organic Chemistry·Alexandru VlasceanuMogens Brøndsted Nielsen
Nov 15, 2017·Nature Communications·Grace G D HanJeffrey C Grossman
Dec 20, 2017·The Journal of Physical Chemistry Letters·Gaurab GangulyAnkan Paul
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Mar 1, 1999·Angewandte Chemie·Luca GobbiFrançois Diederich
Sep 1, 2018·Chemical Society Reviews·Liqi DongWei Feng

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Citations

Feb 25, 2020·Chemistry : a European Journal·Anne Ugleholdt PetersenMogens Brøndsted Nielsen
Oct 1, 2021·Chemical Society Reviews·Jana VolarićBen L Feringa

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

Open Babel
GaussView
CAM
Gaussian

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