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Issue 43, 2018
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Structure–function relationships of donor–acceptor Stenhouse adduct photochromic switches

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Abstract

The first in-depth, systematic study of the photoswitching properties of Donor–Acceptor Stenhouse Adducts (DASAs) is reported. Barbituric acid derived DASAs functionalised with 14 different amines ranging from dimethylamine to 4-methoxy-N-methylaniline were structurally characterised in solution using 1H and 13C NMR spectroscopy and, in eight cases, in the solid state by single crystal X-ray diffraction. The distribution of coloured and colourless isomers in the dark, their photostationary states under irradiation, apparent thermal half-lives, and fatigue resistance are systematically compared. A simple kinetic model is used to characterise photoswitching behaviour and reveals that minor structural modifications can significantly improve the photoswitching properties of DASA photochromes. These modifications result in excellent photoswitching properties for ‘1st generation’ DASAs in chloroform, including exceptional fatigue resistance, opening the door for these photochromic molecules to find widespread applications.

Graphical abstract: Structure–function relationships of donor–acceptor Stenhouse adduct photochromic switches

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Publication details

The article was received on 20 Jul 2018, accepted on 28 Aug 2018 and first published on 12 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03218A
Citation: Chem. Sci., 2018,9, 8242-8252
  • Open access: Creative Commons BY license
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    Structure–function relationships of donor–acceptor Stenhouse adduct photochromic switches

    N. Mallo, E. D. Foley, H. Iranmanesh, A. D. W. Kennedy, E. T. Luis, J. Ho, J. B. Harper and J. E. Beves, Chem. Sci., 2018, 9, 8242
    DOI: 10.1039/C8SC03218A

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