2,5-Dialkoxylphenyl-1,3,4-oxadiazoles as efficient organogelators and their self-assembling property

Abstract

Four 2,5-dialkoxylphenyl-1,3,4-oxadiazoles are shown to be efficient organogelators. These compounds readily form stable gels in many organic solvents and their gelation property as well as supramolecular structures were investigated by scanning electron microscopy (SEM), X-ray diffraction (XRD), ¹H nuclear magnetic resonance (¹H NMR), and ultraviolet-visible spectroscopy (UV-vis). The results indicate that the gelator molecules self-assemble into gels with elongated fibrous networks and layer structures, and van der Waals interaction is the main driving force.

Keywords

1,3,4-oxadiazoles / organogelator / self-assembly

References

[1] TerechP, WeissR G. Low molecular mass gelators of organic liquids and the properties of their gels. Chemical Reviews, 1997, 97(8): 3133-3160

[2] GeorgeM, WeissR G. Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids. Accounts of Chemical Research, 2006, 39(8): 489-497

[3] WangX, PengQ, LiY. Interface-mediated growth of monodispersed nanostructures. Accounts of Chemical Research, 2007, 40(8): 635-643

[4] DastidarP. Supramolecular gelling agents: can they be designed? Chemical Society Reviews, 2008, 37(12): 2699-2715

[5] YangZ, XuK, WangL, GuH, WeiH, ZhangM, XuB. Self-assembly of small molecules affords multifunctional supramolecular hydrogels for topically treating simulated uranium wounds. Chemical Communications, 2005, 35(35): 4414-4416

[6] BonacucinaG, CespiM, Misici-FalziM, PalmieriG F. Colloidal soft matter as drug delivery system. Journal of Pharmaceutical Sciences, 2009, 98(1): 1-42

[7] LoveC S, ChechikV, SmithD K, WilsonK, AshworthI, BrennanC. Synthesis of gold nanoparticles within a supramolecular gel-phase network. Chemical Communications, 2005, 15(15): 1971-1973

[8] VemulaP K, JohnG. Smart amphiphiles: hydro/organogelators for in situ reduction of gold. Chemical Communications, 2006, 21(21): 2218-2220

[9] YangX, LuR, XueP, LiB, XuD, XuT, ZhaoY. Carbazole-based organogel as a scaffold to construct energy transfer arrays with controllable fluorescence emission. Langmuir, 2008, 24(23): 13730-13735

[10] DanjoH, HirataK, YoshigaiS, AzumayaI, YamaguchiK. Back to back twin bowls of D₃-symmetric tris(spiroborate)s for supramolecular chain structures. Journal of the American Chemical Society, 2009, 131(5): 1638-1639

[11] SchenningA P H J, JonkheijmP, PeetersE, MeijerE W. Hierarchical order in supramolecular assemblies of hydrogen-bonded oligo(p-phenylene vinylene)s. Journal of the American Chemical Society, 2001, 123(3): 409-416

[12] JonkheijmP, MiuraA, ZdanowskaM, HoebenF J M, De FeyterS, SchenningA P H J, De SchryverF C, MeijerE W. π-conjugated oligo-(p-phenylenevinylene) rosettes and their tubular self-assembly. Angewandte Chemie International Edition, 2004, 43(1): 74-78

[13] HirstA R, CoatesI A, BoucheteauT R, MiravetJ F, EscuderB, CastellettoV, HamleyI W, SmithD K. Low-molecular-weight gelators: elucidating the principles of gelation based on gelator solubility and a cooperative self-assembly model. Journal of the American Chemical Society, 2008, 130(28): 9113-9121

[14] RavindraK C, VagdeviH M, PadmashaliB. Synthesis, antimicrobial and antiinflammatory activities of 1,3,4-oxadiazoles linked to naphtho[2,1-b]furan. Indian Journal of Chemistry Sect. B, 2006, 45B: 2506-2511

[15] ChenH, LiZ, HanY. Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (Alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles). Journal of Agricultural and Food Chemistry, 2000, 48(11): 5312-5315

[16] XuZ W, LiY, MaX M, GaoX D, TianH. Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives. Tetrahedron, 2008, 64(8): 1860-1867

[17] MitschkeU, BauerleP. The electroluminescence of organic materials. Journal of Materials Chemistry, 2000, 10(7): 1471-1507

[18] LuW, LawY C, HanJ, ChuiS S Y, MaD L, ZhuN, CheC M. A dicationic organoplatinum(II) complex containing a bridging 2,5-bis-(4-ethynylphenyl)-[1,3,4]oxadiazole ligand behaves as a phosphorescent gelator for organic solvents. Asian Journal of Chemistry, 2008, 3(1): 59-69

[19] HanJ, ChuiS S Y, CheC M. Thermotropic liquid crystals based on extended 2,5-disubstituted-1,3,4-oxadiazoles: structure-property relationships, variable-temperature powder X-ray diffraction, and small-angle X-ray scattering studies. Asian Journal of Chemistry, 2006, 1(6): 814-825

[20] DongX L, HuangY D. Synthesis of 2,5-bis(4-alkoxy-phenyl)-1,3,4-oxadiazoles. Chemical Industry and Engineering, 2013, 30: 36-39 (in Chinese)

[21] HuangY D, DongX L, ZhangL L, ChaiW, ChangJ Y. Structure-property correlation of benzoyl thiourea derivatives as organogelators. Journal of Molecular Structure, 2013, 1031: 43-48

[22] EldridgeJ E, FerryJ D. Studies of the cross-linking process in gelatin gels. III. Dependence of melting point on concentration and molecular weight. Journal of Physical Chemistry, 1954, 58(11): 992-995

[23] HuangY D, TuW, YuanY Q, FanD L. Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors. Tetrahedron, 2014, 70(6): 1274-1282

Acknowledgement

This work was financially supported by the Graduate School of Tianjin University.

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg