Optimized synthetic strategies for the preparation of photoswitchable molecular scaffolds based on stilbene or on thioaurone chromophores and their conformationally directing properties, as studied by computations and by NMR spectroscopy, are addressed. For the stilbene peptidomimetics 1, 2 and 3, the length of connecting linkers between the chromophore and the peptide strands was varied, resulting in photochromic dipeptidomimetics with various flexibility. Building blocks of higher rigidity, based on para-substituted thioaurone (4 and 6) and meta-substituted thioaurone chromophores (5 and 7) are shown to have a stronger conformationally directing effect. Design, synthesis, theoretical and experimental conformational analyses are presented.
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http://dx.doi.org/10.1039/b812001c | DOI Listing |
Chemistry
August 2023
Université Paris Cité, CNRS, Inserm, CiTCoM, 75006, Paris, France.
Thioaurone chromophores, part of the indigoid family and commonly named hemithioindigos, have recently gained attention due to their interesting photoswitching properties. The study focuses on heterocyclic hemithioindigos (Het-HTIs) and investigates their synthesis using electron-rich and electron-poor heterocycles and modifications to the thioindigo moiety. Furthermore, it aims to evaluate the photoswitching performances of these synthesised compounds, with a particular emphasis on the influence of the heterocycles on the photoisomerization capabilities, which was found to be more prominent than the modifications made to the thioindigo moiety.
View Article and Find Full Text PDFOrg Biomol Chem
December 2008
Dept. of Medicinal Chemistry, Uppsala University, Box 574, 751 23, Uppsala, Sweden.
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