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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

Frontiers of Chemical Science and Engineering  2016, Vol. 10 Issue (4): 552-561   https://doi.org/10.1007/s11705-016-1589-8
  本期目录
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 δp-δh 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 δp-δh diagrams can be used to estimate the behavior of three compounds in any untested solvent.

Key wordsiodo triazole    azobenzene    photoresponsive organogel    gelator-solvent effect
收稿日期: 2016-04-22      出版日期: 2016-11-29
Corresponding Author(s): Yaodong Huang   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2016, 10(4): 552-561.
Ziyan Li,Yaodong Huang,Dongli Fan,Huimin Li,Shuxue Liu,Luyuan Wang. Synthesis and properties of novel organogelators functionalized with 5-iodo-1,2,3-triazole and azobenzene groups. Front. Chem. Sci. Eng., 2016, 10(4): 552-561.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-016-1589-8
https://academic.hep.com.cn/fcse/CN/Y2016/V10/I4/552
Fig.1  
Solvent A1 A2 A3 B1 B2
Petroleum ether P 35 20 P P
Cyclohexane 30 25 15 PG 25
Hexane P 33 19 P P
Carbon tetrachloride 50 28 14 P 48
Methylene chloride S 60 16 25 4
Tetrahydrofuran PG PG 20 42 13
Ethyl acetate 20 17 8 PG 12
Chloroform S S 14 44 15
Acetone P P 47 PG Ins
Acetonitrile Ins Ins Ins Ins Ins
Dioxane P P 45 P 50
Pyridine PG PG 52 PG PG
Butyl alcohol PG PG PG 50 14
Isopropyl alcohol P P P Ins Ins
Methanol Ins Ins Ins Ins Ins
Ethanol Ins Ins Ins Ins Ins
Triethy lamine P P P P P
Benzene S S 8 50 30
Toluene PG PG 46 45 25
N,N-dimethylformamide P P P P P
Ethyl ether Ins Ins Ins 20 10
Carbon disulfide 42 36 12 11 3
1,2-dichloroethane 35 20 10 33 20
Chlorobenzene 28 15 8 40 13
Tab.1  
Fig.2  
Fig.3  
Fig.4  
Fig.5  
Fig.6  
Fig.7  
Solvent δd δp δh
Cyclohexane 16.7 0 0
Tetrachloromethane 16.9 0 0
1,2-Dichloroethane 18.1 5.3 4.1
?Ethyl acetate 15.2 5.3 9.2
Carbon disulfide 18.3 0 0
Chlorobenzene 18.9 4.3 2.1
Tetrahydrofuran 17.85 5.7 8.0
?Toluene 17.7 1.4 2
Dichlormethane 17.8 6.4 6.1
?Pyridine 19.5 8.8 5.9
Chloroform 17.9 3.1 5.7
Benzene 18.05 1 2
Dioxane 18.25 1.8 7.4
Butanol 16 5.7 15.8
Hexane 14.8 0 0
Acetonitrile 15.8 18.0 6.1
Methanol 15.2 12.3 22.3
Ethanol 15.8 8.8 19.5
Diethyl?ether 14.4 2.9 5.1
Dimethyl formamide 17.4 13.7 11.3
Acetone 15.5 10.4 7
Isopropanol 15.8 6.1 16.4
Tab.2  
Fig.8  
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