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

Abstract

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 ¹H 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.

Graphical abstract

Keywords

iodo triazole / azobenzene / photoresponsive organogel / gelator-solvent effect

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Acknowledgements

This work was supported by the Natural Science Foundation of Tianjin (No. 15JCYBJC20100).

RIGHTS & PERMISSIONS

2016 Higher Education Press and Springer-Verlag Berlin Heidelberg