Abstract
In this paper, new azobenzene imide derivatives with different substituent groups were designed and synthesized. Their gelation behaviors in 21 solvents were tested as novel low-molecular-mass organic gelators. It was shown that the alkyl substituent chains and headgroups of azobenzene residues in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. More alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. Scanning electron microscopy and atomic force microscopy observations revealed that the gelator molecules self-assemble into different aggregates, from wrinkle, lamella, and belt to fiber with the change of solvents. Spectral studies indicated that there existed different H-bond formations between amide groups and conformations of methyl chains. The present work may give some insight to the design and character of new organogelators and soft materials with special molecular structures.
Highlights
It is well known that organogels are one class of important soft materials, in which organic solvents are immobilized by gelators [1,2,3,4,5,6]
It seemed that more alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents
The reasons for the strengthening of the gelation behaviors can be assigned to the change of the spatial conformation of the gelators due to the more alkyl substituent chains in molecular skeletons, which may increase the ability of the gelator molecules to self-assemble into ordered structures, a necessity for forming organized network structures
Summary
It is well known that organogels are one class of important soft materials, in which organic solvents are immobilized by gelators [1,2,3,4,5,6]. The gels based on LMOGs are usually considered as supramolecular gels, in which the gelator molecules self-assemble into three-dimensional networks in which the solvent is trapped via various non-covalent interactions, such as hydrogen bonding, π-π stacking, van der Waals interaction, dipole-dipole interaction, coordination, solvophobic interaction, and hostguest interaction [15,16,17,18,19,20]. Therein, we have investigated the spacer effect on the microstructures of such organogels and found that various kinds of hydrogen bond interactions among the molecules play an important role in the formation of gels
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