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

doi:10.1007/s11705-017-1683-6

Front. Chem. Sci. Eng.

2018, Vol. 12

Issue (2) : 252-261 https://doi.org/10.1007/s11705-017-1683-6

RESEARCH ARTICLE

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

Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China

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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.

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

Corresponding Author(s): Yaodong Huang

Just Accepted Date: 25 September 2017 Online First Date: 31 October 2017 Issue Date: 09 May 2018

Cite this article:

Yaodong Huang,Shuxue Liu,Zhuofeng Xie, et al. Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response[J]. Front. Chem. Sci. Eng., 2018, 12(2): 252-261.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-017-1683-6
https://academic.hep.com.cn/fcse/EN/Y2018/V12/I2/252

Fig.1 Scheme 1 Two organogelators with unusual intermolecular C–I···O XB interaction in reference ²⁶

Fig.2 Scheme 2 Synthetic route for compounds 1-6, C1 and C2. (a) n-RBr (CH₃I was used for the synthesis of 4-methoxyl ethynylbenzene), K₂CO₃, DMF, 70–80 °C, 6 h; (b) trimethylsilylacetylene, CuI, Pd(Ph₃P)₂Cl₂, THF, Et₃N, r.t., 8 h; (c) K₂CO₃, THF, MeOH, r.t., 12 h; (d) CuCl, ICl, THF, Et₃N, r.t., 48 h

Tab.1 Gelation properties of 1–6 in organic solvents^a)

Fig.3 Perspective view of C2 showing 30% probability ellipsoids for the non-hydrogen atoms and the numbering scheme of the atoms in the molecule

Fig.4 The arrangement of two adjacent molecules of C2 showing intermolecular non-classical hydrogen bonding interaction

Fig.5 The crystal packing mode of C2 displaying non-classical hydrogen bonding interaction

Tab.2 Non-classic hydrogen bonds and their angles of the compound C2

Fig.6 SEM images of xerogels from compounds 2, 3 and 5. (a) 3 in ethyl acetate; (b) 2 in acetonitrile; (c) 2 in CCl₄; (d) 2 in DMF; (e) 2 in n-butanol; (f) 5 in n-butanol. All the gels have a concentration of 5.0% and were dried in atmosphere for 48 h to form xerogels

Fig.7 XRD patterns of the xerogels obtained from the gels of (a) 5 in n-butanol, (b) 2 in n-butanol, (c) 2 in CCl₄, and (d) 2 in DMF

Fig.8 Temperature dependent ¹H NMR spectra of gel 2 in CD₃CN (10 mg/mL)

Fig.9 ¹H NMR spectra of 2 in CDCl₃ at different concentrations

Fig.10 Reversible gel-sol transitions of 5/ethanol gel tuning by redox-reaction and different chemicals

Fig.11 UV absorption spectra of (a) 2 ethanol solution (5.5 × 10^–⁵ mol/L) with different concentrations of Hg²⁺ and (b) 5 ethanol soltion (7.3 × 10^–⁵ mol/L) with different concentrations of Cu²⁺ at room temperature

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