Synthesis and properties of novel organogelators functionalized with 5-iodo-1,2,3-triazole and azobenzene groups

• Published in: Frontiers of chemical science and engineering 2016-12, Vol.10 (4), p.552-561
• Main Authors: Li, Ziyan, Huang, Yaodong, Fan, Dongli, Li, Huimin, Liu, Shuxue, Wang, Luyuan
• Format: Article
• Language: English
• Subjects: Azo compounds; Chemistry; Chemistry and Materials Science; Dipole interactions; Gelation; Industrial Chemistry/Chemical Engineering; Nanotechnology; NMR; Nuclear magnetic resonance; Research Article; Solubility parameters; Solvents; Triazoles
• ISSN: 2095-0179; 2095-0187
• DOI: 10.1007/s11705-016-1589-8

Two series of 5-iodo-1,2,3-triazole derivatives containing azobenzene group(s) were synthesized and their gelling properties were tested. Those containing two azobenzene groups ( B series) have better gelation performance than those containing one azobenzene group ( A series). The microstructure of organogels and the driving force of gelation were investigated by scanning electron microscopy and 1 H NMR, respectively. It was found that π-π stacking, van der Waals interaction, and dipole-dipole interaction were the main forces of gelation. All the tested organogels are photoresponsive and those from B series are smarter than that from A series. Henry δ p - δ h diagrams of compounds A1 , A2 , and B2 were constructed on the basis of their gelation performance and the Hansen solubility parameters of related solvents. The constructed Henry δ p - δ h diagrams can be used to estimate the behavior of three compounds in any untested solvent.