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.

Key words： organogelator; 1,2,3-triazole derivatives; self-assembly; halogen bonding; cation response

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.

References

1 Sung S, Park S, Lee W J, Son J, Kim C H, Kim Y, Noh D Y, Yoon M H. Low-voltage flexible organic electronics based on high-performance sol-gel titanium dioxide dielectric. ACS Applied Materials & Interfaces, 2015, 7(14): 7456–7461

2 Das A, Ghosh S. Supramolecular assemblies by charge-transfer interactions between donor and acceptor chromophores. Angewandte Chemie International Edition, 2014, 45(18): 2038–2054

3 Babu S S, Praveen V K, Ajayaghosh A. Functional π-gelators and their applications. American Chemical Society, 2014, 114(4): 1973–2129

4 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

5 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

6 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

7 Kumar R J, MacDonald J M, Singh T B, Waddington L J, Holmes A B. Hierarchical self-assembly of semiconductor functionalized peptide α-helices and optoelectronic properties. Journal of the American Chemical Society, 2011, 133(22): 8564–8573

8 Kim H, Chang J Y. White light emission from a mixed organogel of lanthanide(III)-containing organogelators. RSC Advances, 2013, 3(6): 1774–1780

9 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

10 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

11 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

12 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

13 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

14 Zhao Y, Sakai F, Su L, Liu Y, Wei K, Chen G, Jiang M. Progressive macromolecular self-assembly: From biomimetic chemistry to bio-inspired materials. Advanced Materials, 2013, 25(37): 5215–5256

15 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

16 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

17 Sugiyasu K, Fujita N, Shinkai S. Visible-light-harvesting organogel composed of cholesterol-based perylene derivatives. Angewandte Chemie, 2004, 43(10): 1229–1233

18 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

19 Abdallah D J, Weiss R G. Organogels and low molecular-mass organic gelators. Advanced Materials, 2000, 12(17): 1237–1247

20 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

21 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

22 Bhattacharjee S, Bhattacharya S. Remarkable role of C–I···N halogen bonding in thixotropic ‘halo’gel formation. Langmuir, 2016, 32(17): 4270–4277

23 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 self-assembly by iodination. Nature Communications, 2015, 6: 7574

24 Huang Y, Zhang Y, Yuan Y, Cao W. Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: Properties and gelator-solvent interaction. Tetrahedron, 2015, 71(14): 2124–2133

25 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

26 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

27 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

28 Schulze B, Schubert U S. Beyond click chemistry—supramolecular interactions of 1,2,3-triazoles. Chemical Society Reviews, 2014, 43(8): 2522–2571

29 Janiak C. A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry, 2000, 32(11): 3885–3896

30 Linse P. Orientation-averaged benzene-benzene potential of mean force in aqueous solution. Journal of the American Chemical Society, 1993, 115(19): 8793–8797

31 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

32 Bhalla V, Singh H, Kumar M, Prasad S K. Triazole-modified triphenylene derivative: Self-assembly and sensing applications. Langmuir, 2011, 27(24): 15275–15281