Direct evidence for the effect of intermolecular hydrogen bonding on organogels

Abstract

In order to get direct evidence for the effect of intermolecular hydrogen bonding on the organogels, one amide group in N-(3, 4, 5-octyloxybenzoyl)-N′-(4′-aminobenzoyl)hydrazine(D8) was replaced by a Schiff base group, forming N-(3,4,5-octyloxybenzoyl)-N′-(4′-amidobenzoyl) acylhydrazone(T8SchA). D8 and T8SchA organogels in cyclohexane show the same hexagonal columnar structure. And the hydrogen bonding was demonstrated to be still interacting in the organogels. However, although the molecular geometry of D8 was well retained in T8SchA, the molecular dipole moment of T8SchA is bigger than that of D8 due to the reduction of the number of hydrogen bonds. Thus, the decreased gelling stability of T8SchA compared to that of D8 can only be attributed to the reduction of the number of intermolecular hydrogen bonds, which provides direct evidence that intermolecular hydrogen bonding plays an important role in stabilising organogels.

Keywords

Intermolecular hydrogen bonding / Organogel / Hexagonal columnar structure / Schiff base / Hydrazide derivative

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