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Evidence of Nanotubular Self-Organization in Solution and Solid States of Heterochiral Cyclo 1:1 [alpha/alpha-N-alpha-Bn-hydrazino]mers Series

Abstract : The cyclization of heterochiral 1:1 [alpha/alpha-N-alpha-Bn-hydrazino]mers leads to the corresponding cyclotetramer and cyclohexamer 3 and 4. X-ray crystallographic analysis of 3 unveils its ability to self-assemble into nanotubular structures. Further experiments conducted in the solid state through SEM analyses demonstrate the capability of 3 and 4 to form aerogels consisting of a network of nontwisted fibers, thus confirming the presence of self-organization within this series of mixed-hydrazinopeptides. Subsequent FTIR and NMR studies demonstrate the presence of an equilibrium between monomeric (intramolecular H-bonds) and nanotubular (intermolecular H-bonds) forms in solution. This equilibrium can be modified by varying the solvent.
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https://hal.univ-lorraine.fr/hal-01497723
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Submitted on : Wednesday, March 29, 2017 - 10:46:42 AM
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Ralph-Olivier Moussodia, Samir Acherar, Eugenie Romero, Claude Didierjean, Brigitte Jamart-Grégoire. Evidence of Nanotubular Self-Organization in Solution and Solid States of Heterochiral Cyclo 1:1 [alpha/alpha-N-alpha-Bn-hydrazino]mers Series. Journal of Organic Chemistry, American Chemical Society, 2015, 80 (6), pp.3022-3029. ⟨10.1021/jo502684g⟩. ⟨hal-01497723⟩

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