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Templated Chromophore Assembly by Dynamic Covalent Bonds
Author(s) -
Rocard Lou,
Berezin Andrey,
De Leo Federica,
Bonifazi Davide
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507186
Subject(s) - chromophore , covalent bond , chemistry , disulfide bond , dynamic covalent chemistry , molecular dynamics , rotaxane , photochemistry , acceptor , hydrazone , absorption (acoustics) , molecule , materials science , stereochemistry , computational chemistry , supramolecular chemistry , organic chemistry , biochemistry , physics , condensed matter physics , composite material
Through the simultaneous use of three orthogonal dynamic covalent reactions, namely disulfide, boronate, and acyl hydrazone formation, we conceived a facile and versatile protocol to spatially organize tailored chromophores, which absorb in the blue, red, and yellow regions, on a preprogrammed α‐helix peptide. This approach allowed the assembly of the dyes in the desired ratio and spacing, as dictated by both the relative positioning and distribution of the recognition units on the peptide scaffold. Steady‐state UV/Vis absorption and emission studies suggest an energy transfer from the yellow and red donors to the blue acceptor. A molecular dynamics simulation supports the experimental findings that the helical structure is maintained after the assembly and the three dyes are confined in defined conformational spaces.