Regulation of substituent groups on morphologies and self-assembly of organogels based on some azobenzene imide derivatives

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.

Self-assembly of organogels via new luminol imide derivatives: diverse nanostructures and substituent chain effect

“…For the case of TC12-Lu, no gel can be prepared due to the shortest alkyl substituent chains, as shown in Figure 9b. Meanwhile, it should be noted that this phenomenon is similar to the results of recent reports [49,50]. Therein, the substituent groups in azobenzene residue or benzimidazole/benzothiazole imide derivatives can have a profound effect upon the gelation abilities and the as-formed nanostructures of the studied compounds.…”

Spacer effect on nanostructures and self-assembly in organogels via some bolaform cholesteryl imide derivatives with different spacers

“…Moreover, for CH-C2 and CH-N1, the inefficient or poor gelation behaviors in the present solvents may be mainly attributed to the too rigid or too flexible spacers in molecular skeletons, which cannot cause enough intermolecular forces to make the molecules align and stack in an organized way to form various nanostructures. Meanwhile, it should be noted that this phenomenon can be compared with the results of our recent works [24,25,48]. Therein, functionalized imide derivatives with the substituent groups of cholesteryl, azobenzene, luminol, and benzimidazole/benzothiazole residue can have a profound effect on the gelation abilities and the as-formed nanostructures of the studied compounds.…”

Self-Assembly and Drug Release Capacities of Organogels via Some Amide Compounds with Aromatic Substituent Headgroups

“…The obtained experimental values of TC16-Np and TC16-Fl in gels were 2.16 and 2.02 nm, which was near the calculated molecular length, suggesting cooperative stacking in an organized way to form various nanostructures. Meanwhile, it should be noted that this phenomenon can be compared with the results of our recent works [40,41,42]. Therein, functionalized amide derivatives with the substituent groups of cholesteryl, azobenzene, and luminol residues can have a profound effect on the gelation abilities and the as-formed nanostructures of the studied compounds.…”