Peptide-Driven Charge-Transfer Organogels Built from Synergetic Hydrogen Bonding and Pyrene-Naphthalenediimide Donor-Acceptor Interactions

The peptide-driven formation of charge transfer supramolecular gels featuring both directional hydro-gen-bonding and donor–acceptor (D-A) complexation is reported. Our design consists of the coassembly of two dipep-tide–chromophore conjugates, namely diphenylalanine 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 and1H NMR spectroscopy studiesunderlined the pivotal role of hydrogen bonding in the gelation process, and electronic paramagnetic resonance (EPR)measurements unraveled the advantage of preorganized CTsupramolecular architectures for charge transport over solutions containing non-coassembled D and A molecular systems.