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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507186
Subject(s) - chromophore , covalent bond , disulfide bond , molecular dynamics , chemistry , acceptor , photochemistry , hydrazone , absorption (acoustics) , dynamic covalent chemistry , materials science , molecule , stereochemistry , computational chemistry , organic chemistry , supramolecular chemistry , biochemistry , physics , composite material , condensed matter physics
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.