Peptide-driven charge-transfer organogels built from synergetic hydrogen bonding and pyrene–naphthalenediimide donor–acceptor interactions

Silvia Bartocci, José Augusto Berrocal, Paola Guarracino, Maxime Grillaud, Lorenzo Franco, Miriam Mba

Research output: Contribution to journalArticleAcademicpeer-review

8 Citations (Scopus)
104 Downloads (Pure)

Abstract

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 1H 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.

Original languageEnglish
Pages (from-to)2920-2928
Number of pages9
JournalChemistry : A European Journal
Volume24
Issue number12
DOIs
Publication statusPublished - 26 Feb 2018

Keywords

  • charge transfer
  • EPR spectroscopy
  • gels
  • peptides
  • self-assembly

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