Premium
Peptide‐Driven Charge‐Transfer Organogels Built from Synergetic Hydrogen Bonding and Pyrene–Naphthalenediimide Donor–Acceptor Interactions
Author(s) -
Bartocci Silvia,
Berrocal José Augusto,
Guarracino Paola,
Grillaud Maxime,
Franco Lorenzo,
Mba Miriam
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704487
Subject(s) - supramolecular chemistry , pyrene , hydrogen bond , chemistry , acceptor , photochemistry , electron paramagnetic resonance , chromophore , dipeptide , supramolecular assembly , conjugated system , crystallography , polymer chemistry , peptide , molecule , polymer , organic chemistry , crystal structure , nuclear magnetic resonance , biochemistry , physics , condensed matter physics
The peptide‐driven formation of charge transfer (CT) supramolecular gels featuring both directional hydrogen‐bonding and donor–acceptor (D‐A) complexation is reported. Our design consists of the coassembly of two dipeptide–chromophore conjugates, namely diphenylalanine (FF) dipeptide conveniently functionalized at the N‐terminus with either a pyrene ( Py‐1 , donor) or naphthalene diimide ( NDI‐1 , acceptor). UV/Vis spectroscopy confirmed the formation of CT complexes. FTIR and 1 H NMR spectroscopy studies underlined the pivotal role of hydrogen bonding in the gelation process, and electronic paramagnetic resonance (EPR) measurements unraveled the advantage of preorganized CT supramolecular architectures for charge transport over solutions containing non‐coassembled D and A molecular systems.