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

• Published in: Frontiers of chemical science and engineering 2018, Vol.12 (2), p.252-261
• Main Authors: Huang, Yaodong, Liu, Shuxue, Xie, Zhuofeng, Sun, Zipei, Chai, Wei, Jiang, Wei
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Copper; Gelation; Gels; Hydrogen bonding; Industrial Chemistry/Chemical Engineering; Mercury (metal); Nanotechnology; Organic chemistry; Position measurement; Research Article; Scanning electron microscopy; Single crystals; Sol-gel processes; Substitution reactions; X-ray diffraction
• ISSN: 2095-0179; 2095-0187
• DOI: 10.1007/s11705-017-1683-6

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 2+ , whereas hydrogenous gels can respond to Hg 2+ and Cu 2+ . 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 ( C2 ) 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.