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.
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Sung S, Park S, Lee W J, Son J, Kim C H, Kim Y, Noh D Y, YoonM H. Low-voltage flexible organic electronics based on highperformance sol-gel titanium dioxide dielectric. ACS Applied Materials & Interfaces, 2015, 7(14): 7456–7461
Das A, Ghosh S. Supramolecular assemblies by charge-transfer interactions between donor and acceptor chromophores. Angewandte Chemie International Edition, 2014, 45(18): 2038–2054
Babu S S, Praveen V K, Ajayaghosh A. Functional p-gelators and their applications. American Chemical Society, 2014, 114(4): 1973–2129
Han J, Song J, Hao Z, Yu H, Han J. Self-assembly of Schiff base organogelator with enhanced fluorescence emission. Chinese Journal of Chemistry, 2015, 33(1): 137–140
Choi T J, Chang J Y. Preparation of thermochromic polymer nanocomposite films from polymerizable organogels of oligothiophene-based organogelators. Macromolecular Research, 2016, 24 (12): 1055–1061
Lüer L, Rajendran S K, Stoll T, Ganzer L, Rehault J, Coles D M, Lidzey D, Virgili T, Cerullo G. Lévy defects in matrix-immobilized J aggregates: Tracing intra-and intersegmental exciton relaxation. Journal of Physical Chemistry Letters, 2017, 8(3): 547–552
Kumar R J, MacDonald J M, Singh T B, Waddington L J, Holmes A B. Hierarchical self-assembly of semiconductor functionalized peptide a-helices and optoelectronic properties. Journal of the American Chemical Society, 2011, 133(22): 8564–8573
Kim H, Chang J Y. White light emission from a mixed organogel of lanthanide(III)-containing organogelators. RSC Advances, 2013, 3 (6): 1774–1780
Pang X, Yu X, Xie D, Li Y, Geng L, Ren J, Zhen X. Tunable multicolor emissions in monocomponent gel system by varying solvents, temperature and fluoride anion. Organic & Biomolecular Chemistry, 2016, 14(47): 11176–11182
Sun J, Xue P, Sun J, Gong P, Wang P, Lu R. Strong blue emissive nanofibers constructed from benzothizole modified tert-butyl carbazole derivative for the detection of volatile acid vapors. Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices, 2015, 3(34): 8888–8894
Zhai Y, Chai W, Cao W W, Sun Z P, Huang Y D. Organogelators based on p-alkoxylbenzamide and their self-assembling properties. Frontiers of Chemical Science and Engineering, 2015, 9(4): 488–493
Cheng H B, Li Z, Huang Y D, Liu L, Wu H C. A pillararene-based AIE-active supramolecular system for simultaneous detection and removal of mercury(II) in water. ACS Applied Materials & Interfaces, 2017, 9(13): 11889–11894
Zhao Z, Lam J W Y, Tang B Z. Self-assembly of organic luminophores with gelation-enhanced emission characteristics. Soft Matter, 2013, 9(18): 4564–4579
Zhao Y, Sakai F, Su L, Liu Y, Wei K, Chen G, Jiang M. Progressive macromolecular self-assembly: From biomimetic chemistry to bioinspired materials. Advanced Materials, 2013, 25(37): 5215–5256
Piepenbrock M O M, Lloyd G O, Clarke N, Steed J W. Metal-and anion-binding supramolecular gels. Chemical Reviews, 2010, 110 (4): 1960–2004
Van Herrikhuyzen J, George S J, Vos M R J, Sommerdijk N A J M, Ajayaghosh A, Meskers S C J, Schenning A P H J. Self-assembled hybrid oligo(p-phenylenevinylene)-gold nanoparticle tapes. Angewandte Chemie, 2007, 46(11): 1825–1828
Sugiyasu K, Fujita N, Shinkai S. Visible-light-harvesting organogel composed of cholesterol-based perylene derivatives. Angewandte Chemie, 2004, 43(10): 1229–1233
Suzuki M, Yumoto M, Kimura M, Shiraib H, Hanabusa K. Novel family of low molecular weight hydrogelators based on L-lysine derivatives. Chemical Communications, 2002, 33(8): 884–885
Abdallah D J, Weiss R G. Organogels and low molecular-mass organic gelators. Advanced Materials, 2000, 12(17): 1237–1247
Meazza L, Foster J A, Fucke K, Metrangolo P, Resnati G, Steed J W. Halogen-bonding-triggered supramolecular gel formation. Nature Chemistry, 2013, 5(1): 42–47
Feng Y, Chen H, Liu Z X, He Y M, Fan Q H. A pronounced halogen effect on the organogelation properties of peripherally halogen functionalized poly(benzyl ether) dendrons. Chemistry (Weinheim an der Bergstrasse, Germany), 2016, 22(14): 4980–4990
Bhattacharjee S, Bhattacharya S. Remarkable role of C–I$$$N halogen bonding in thixotropic ‘halo’gel formation. Langmuir, 2016, 32(17): 4270–4277
Bertolani A, Pirrie L, Stefan L, Houbenov N, Haataja J S, Catalano L, Terraneo G, Giancane G, Valli L, Milani R, Ikkala O, Resnati G, Metrangolo P. Supramolecular amplification of amyloid selfassembly by iodination. Nature Communications, 2015, 6: 7574
Huang Y, Zhang Y, Yuan Y, Cao W. Organogelators based on iodo 1, 2, 3-triazole functionalized with coumarin: Properties and gelatorsolvent interaction. Tetrahedron, 2015, 71(14): 2124–2133
Li Z, Huang Y, Fan D, Li H, Liu S, Wang L. Synthesis and properties of novel organogelators functionalized with 5-iodo-1, 2, 3-triazole and azobenzene groups. Frontiers of Chemical Science and Engineering, 2016, 10(4): 552–561
Huang Y D, Li H M, Li Z Y, Zhang Y, Cao W W, Wang L Y, Liu S X. Unusual C–I...O halogen bonding in triazole derivatives: Gelation solvents at two extremes of polarity and formation of superorganogels. Langmuir, 2017, 33(1): 311–321
Wu Y M, Deng J, Li Y, Chen Q Y. Regiospecific synthesis of 1, 4, 5-trisubstituted-1, 2, 3-triazole via one-pot reaction promoted by copper(I) salt. Synthesis, 2005, 36(43): 1314–1318
Schulze B, Schubert U S. Beyond click chemistry—supramolecular interactions of 1, 2, 3-triazoles. Chemical Society Reviews, 2014, 43 (8): 2522–2571
Janiak C. A critical account on p-p stacking in metal complexes with aromatic nitrogen-containing ligands. Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry, 2000, 32(11): 3885–3896
Linse P. Orientation-averaged benzene-benzene potential of mean force in aqueous solution. Journal of the American Chemical Society, 1993, 115(19): 8793–8797
Lai L L, Wang C H, Hsieh W P, Lin H C. Synthesis and characterization of liquid crystalline molecules containing the ouinoline unit. Molecular Crystals and Liquid Crystals (Philadelphia, Pa.), 1996, 287(1): 177–181
Bhalla V, Singh H, Kumar M, Prasad S K. Triazole-modified triphenylene derivative: Self-assembly and sensing applications. Langmuir, 2011, 27(24): 15275–15281
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This work was supported by the Natural Science Foundation of Tianjin (No. 15JCYBJC20100).
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Huang, Y., Liu, S., Xie, Z. et al. Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response. Front. Chem. Sci. Eng. 12, 252–261 (2018). https://doi.org/10.1007/s11705-017-1683-6
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DOI: https://doi.org/10.1007/s11705-017-1683-6