Solvent-tunable morphology and emission of pyrene-dipeptide organogels

Journal of Peptide Science : an Official Publication of the European Peptide Society
S BartocciM Mba

Abstract

Two pyrene based organogelators in which the pyrene moiety has been linked to the diphenylalanine dipeptide have been synthesized. We show how the solvent can tune both the morphology and the optical properties of the organogels: spherical aggregates with quenched emission were obtained in acetonitrile, whereas an entangled fibrillar network with enhanced emission was formed in o-dichlorobenzene. Fourier transform infrared spectroscopy, circular dichroism and nuclear magnetic resonance spectroscopy experiments suggest that both π-π stacking and hydrogen bonding contribute to the formation of the supramolecular networks. Ultraviolet-visible and steady state emission studies demonstrated the formation of I-aggregates in acetonitrile. In contrast, in o-dichlorobenzene, the formation of J-type aggregates leads to assemblies with enhanced emission. These results give some insight into the important role of the gelling solvent in the morphology of the supramolecular gels and may help in the design of new soft-materials.

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Citations

Apr 5, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Enric MayansCarlos Alemán
Apr 10, 2019·Soft Matter·Aisylu S SafiullinaValery V Gorbatchuk
Jun 27, 2019·Chemical Society Reviews·Bingbing SunJunbai Li
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fanny d'OrlyéAnne Varenne
Dec 8, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Zonglin YangKaiqiang Liu

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