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Coumaric amide rotaxanes: effects of hydrogen bonding and mechanical interlocking on the photochemistry and photophysics

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Abstract

Secondary amide derivatives of coumaric and ferulic acid are shown to undergo photoisomerization, forming a photostationary mixture of E- and Z-isomers. When the same chromophores are incorporated in rotaxanes, the extent of conversion to the Z-isomers is much smaller. Low temperature fluorescence experiments show that the energy barrier for non-radiative decay of the excited state is higher in the rotaxanes than in the corresponding threads, but the barriers are low in all cases.

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Authors and Affiliations

  1. Van’t Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018, WS Amsterdam, The Netherlands

    Albert M. Brouwer, Sandro M. Fazio & Natalia Haraszkiewicz

  2. School of Chemistry, University of Edinburgh, The King’s Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK

    David A. Leigh & Claire M. Lennon

Authors
  1. Albert M. Brouwer
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  2. Sandro M. Fazio
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  3. Natalia Haraszkiewicz
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  4. David A. Leigh
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  5. Claire M. Lennon
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Correspondence to Albert M. Brouwer or David A. Leigh.

Additional information

This paper was published as part of the special issue to commemorate the 70th birthday of Vincenzo Balzani. Professor Balzani made important contributions to the photochemistry of olefins and to the research on photoactive mechanically interlocked systems (“Molecular machinery”), two topics which come together in this paper.

Electronic supplementary information (ESI) available: Details of NMR and UV spectra resulting from photoisomerization experiments. See DOI: 10.1039/b618795a

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Brouwer, A.M., Fazio, S.M., Haraszkiewicz, N. et al. Coumaric amide rotaxanes: effects of hydrogen bonding and mechanical interlocking on the photochemistry and photophysics. Photochem Photobiol Sci 6, 480–486 (2007). https://doi.org/10.1039/b618795a

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  • DOI: https://doi.org/10.1039/b618795a

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