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

Abstract

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 Hg²⁺, whereas hydrogenous gels can respond to Hg²⁺ and Cu²⁺. 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.

Graphical abstract

Keywords

organogelator / 1,2,3-triazole derivatives / self-assembly / halogen bonding / cation response

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Acknowledgment

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

Electronic Supplementary Material

Supplementary material is available in the online version of this article at http://dx.doi.org/10.1007/s11705-017-1683-6 and is accessible for authorized users.

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2017 Higher Education Press and Springer-Verlag GmbH Germany