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

Ziyan Li,Yaodong Huang,Dongli Fan,Huimin Li,Shuxue Liu,Luyuan Wang

《化学科学与工程前沿（英文）》 2016年第10卷第4期页码 552-561 doi: 10.1007/s11705-016-1589-8

摘要： 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 ( series) have better gelation performance than those containing one azobenzene group ( series). The microstructure of organogels and the driving force of gelation were investigated by scanning electron microscopy and 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 series are smarter than that from series. Henry - diagrams of compounds , , and were constructed on the basis of their gelation performance and the Hansen solubility parameters of related solvents. The constructed Henry - diagrams can be used to estimate the behavior of three compounds in any untested solvent.

关键词： iodo triazole azobenzene photoresponsive organogel gelator-solvent effect

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Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response

Yaodong Huang, Shuxue Liu, Zhuofeng Xie, Zipei Sun, Wei Chai, Wei Jiang

《化学科学与工程前沿（英文）》 2018年第12卷第2期页码 252-261 doi: 10.1007/s11705-017-1683-6

摘要： Two new series of 1,2,3-triazole derivatives, with and without iodo substitution, were synthesized and their gelation properties were measured. It was found that the iodo substitution at position 5 of triazole ring could greatly enhance the gelation ability. Scanning electron microscopy and X-ray diffraction reveal that the structures of the organogels from iodo and hydrogenous gelators are totally different. Iodo gels are selectively responsive to the stimuli of Hg , whereas hydrogenous gels can respond to Hg and Cu . Moreover, the reversible gel-sol transition of hydrogenous gels can be controlled by redox reaction or tuned with suitable chemicals. The single crystal analysis of reference compound ( ) suggests that there are intermolecular and intramolecular non-classical hydrogen bonding interactions but no π-π interaction in hydrogenous gelator. The great difference between the two series of compounds results from the iodo effect and implies the existence of halogen bonding interaction in the iodo compounds.

关键词： organogelator 1 2 3-triazole derivatives self-assembly halogen bonding cation response