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

doi:10.1007/s11705-016-1589-8

Front. Chem. Sci. Eng.

2016, Vol. 10

Issue (4) : 552-561 https://doi.org/10.1007/s11705-016-1589-8

RESEARCH ARTICLE

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

Ziyan Li,Yaodong Huang(

),Dongli Fan,Huimin Li,Shuxue Liu,Luyuan Wang

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 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.

Keywords iodo triazole azobenzene photoresponsive organogel gelator-solvent effect

Corresponding Author(s): Yaodong Huang

Just Accepted Date: 19 August 2016 Online First Date: 14 November 2016 Issue Date: 29 November 2016

Cite this article:

Ziyan Li,Yaodong Huang,Dongli Fan, et al. Synthesis and properties of novel organogelators functionalized with 5-iodo-1,2,3-triazole and azobenzene groups[J]. Front. Chem. Sci. Eng., 2016, 10(4): 552-561.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-016-1589-8
https://academic.hep.com.cn/fcse/EN/Y2016/V10/I4/552

Fig.1 Scheme 1Synthetic route for organogelators A1, A2, A3, B1, and B2

(a) DIPEA, CuI, NBS, THF, r. t., 20 h, ~60%; (b) DIPEA, CuI, NBS, THF, r. t., 28 h, ~50%

Tab.1 Gelation properties of the five synthesized compounds ^a)

Fig.2 Scheme 2The structures of two control compounds C1 and C2

Fig.3 SEM images of xerogels of (a) A1/ethyl acetate, (b) A2/ethyl acetate, (c) A3/ethyl acetate, (d) A3/cyclohexane, (e) A3/chlorobenzene, (f) B2/methylene chloride, (g) B2/ethyl acetate, and (h) B2/n-butyl alcohol. The concentration of all the gels is 20 mg/mL

Fig.4 XRD patterns of xerogels from (a) A3/1,2-dicholoethane gel (20 mg/mL) and (b) B2/1,2-dicholoethane gel (20 mg/mL)

Fig.5 Temperature-dependent ¹H NMR spectra of A3 in CDCl₃ (10 mg/mL)

Fig.6 The phase transitions of A3/1,2-dichloroethane and B2/1,2-dichloroethane systems

Fig.7 UV spectra of the gel-sol and sol-gel transitions of A3/1,2-dichloroethane and B2/1,2-dichloroethane systems. The concentrations are 15 and 20 mg/mL for A3 gel and B2 gel, respectively. (a) A3/1,2-dichloroethane gel irradiated by ultraviolet light; (b) The subsequent sol of (a) irradiated by visible light; (c) B2/1,2-dichloroethane gel irradiated by ultraviolet light; (d) The subsequent sol of (c) irradiated by visible light

Tab.2 The Hansen solubility parameters of the solvents^a)

Fig.8 The δ_p-δ_hdiagrams for (a) A1, (b) A3, and (c) B2

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