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

doi:10.1002/chem.201704487

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 journal › Article › Academic › peer-review

8 Citations (Scopus)

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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 language	English
Pages (from-to)	2920-2928
Number of pages	9
Journal	Chemistry : A European Journal
Volume	24
Issue number	12
DOIs	https://doi.org/10.1002/chem.201704487
Publication status	Published - 26 Feb 2018

Keywords

charge transfer
EPR spectroscopy
gels
peptides
self-assembly

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

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.",

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Peptide-driven charge-transfer organogels built from synergetic hydrogen bonding and pyrene–naphthalenediimide donor–acceptor interactions. / Bartocci, Silvia; Berrocal, José Augusto; Guarracino, Paola; Grillaud, Maxime; Franco, Lorenzo; Mba, Miriam.

In: Chemistry : A European Journal, Vol. 24, No. 12, 26.02.2018, p. 2920-2928.

Research output: Contribution to journal › Article › Academic › peer-review

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AU - Bartocci, Silvia

AU - Berrocal, José Augusto

AU - Guarracino, Paola

AU - Grillaud, Maxime

AU - Franco, Lorenzo

AU - Mba, Miriam

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AB - 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.

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