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

详细信息    查看全文

• 作者：Zipei Sun (1)
  Xuelin Dong (1)
  Yan Zhai (1)
  Ziyan Li (1)
  Yaodong Huang (1)
  
• 关键词：1 ; 3 ; 4 ; oxadiazoles ; organogelator ; selfassembly
• 刊名：Frontiers of Chemical Science and Engineering
• 出版年：2014
• 出版时间：June 2014
• 年：2014
• 卷：8
• 期：2
• 页码：219-224
• 全文大小：
• 参考文献：1. Terech P, Weiss R G. Low molecular mass gelators of organic liquids and the properties of their gels. Chemical Reviews, 1997, 97(8): 3133鈥?160 CrossRef
  2. George M, Weiss R G. Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids. Accounts of Chemical Research, 2006, 39(8): 489鈥?97 CrossRef
  3. Wang X, Peng Q, Li Y. Interface-mediated growth of monodispersed nanostructures. Accounts of Chemical Research, 2007, 40(8): 635鈥?43 CrossRef
  4. Dastidar P. Supramolecular gelling agents: can they be designed? Chemical Society Reviews, 2008, 37(12): 2699鈥?715 CrossRef
  5. Yang Z, Xu K, Wang L, Gu H, Wei H, Zhang M, Xu B. Selfassembly of small molecules affords multifunctional supramolecular hydrogels for topically treating simulated uranium wounds. Chemical Communications, 2005, 35: 4414鈥?416 CrossRef
  6. Bonacucina G, Cespi M, Misici-Falzi M, Palmieri G F. Colloidal soft matter as drug delivery system. Journal of Pharmaceutical Sciences, 2009, 98(1): 1鈥?2
  7. Love C S, Chechik V, Smith D K, Wilson K, Ashworth I, Brennan C. Synthesis of gold nanoparticles within a supramolecular gelphase network. Chemical Communications, 2005, 15: 1971鈥?973 CrossRef
  8. Vemula P K, John G. Smart amphiphiles: hydro/organogelators for in situ reduction of gold. Chemical Communications, 2006, 21: 2218鈥?220 CrossRef
  9. Yang X, Lu R, Xue P, Li B, Xu D, Xu T, Zhao Y. Carbazole-based organogel as a scaffold to construct energy transfer arrays with controllable fluorescence emission. Langmuir, 2008, 24(23): 13730鈥?3735 CrossRef
  10. Danjo H, Hirata K, Yoshigai S, Azumaya I, Yamaguchi K. 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鈥?639 CrossRef
  11. Schenning A P H J, Jonkheijm P, Peeters E, Meijer E W. Hierarchical order in supramolecular assemblies of hydrogenbonded oligo(p-phenylene vinylene)s. Journal of the American Chemical Society, 2001, 123(3): 409鈥?16 CrossRef
  12. Jonkheijm P, Miura A, Zdanowska M, Hoeben F J M, De Feyter S, Schenning A P H J, De Schryver F C, Meijer E W. 蟺-conjugated oligo-(p-phenylenevinylene) rosettes and their tubular self-assembly. Angewandte Chemie International Edition, 2004, 43(1): 74鈥?8 CrossRef
  13. Hirst A R, Coates I A, Boucheteau T R, Miravet J F, Escuder B, Castelletto V, Hamley I W, Smith D 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鈥?121 CrossRef
  14. Ravindra K C, Vagdevi H M, Padmashali B. 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(11): 2506鈥?511
  15. Chen H, Li Z, Han Y. 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鈥?315 CrossRef
  16. Xu Z W, Li Y, Ma X M, Gao X D, Tian H. Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives. Tetrahedron, 2008, 64(8): 1860鈥?867 CrossRef
  17. Mitschke U, Bauerle P. The electroluminescence of organic materials. Journal of Materials Chemistry, 2000, 10(7): 1471鈥?507 CrossRef
  18. Lu W, Law Y C, Han J, Chui S S Y, Ma D L, Zhu N, Che C 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鈥?9 CrossRef
  19. Han J, Chui S S Y, Che C 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鈥?25 CrossRef
  20. Dong X L, Huang Y D. Synthesis of 2,5-bis(4-alkoxy-phenyl)-1,3,4-oxadiazoles. Chemical Industry and Engineering, 2013, 30(2): 36鈥?9 (in Chinese)
  21. Huang Y D, Dong X L, Zhang L L, Chai W, Chang J Y. Structureproperty correlation of benzoyl thiourea derivatives as organogelators. Journal of Molecular Structure, 2013, 1031: 43鈥?8 CrossRef
  22. Eldridge J E, Ferry J 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鈥?95 CrossRef
  23. Huang Y D, Tu W, Yuan Y Q, Fan D L. Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors. Tetrahedron, 2014, 70(6): 1274鈥?282 CrossRef
  
• 作者单位：Zipei Sun (1)
  Xuelin Dong (1)
  Yan Zhai (1)
  Ziyan Li (1)
  Yaodong Huang (1)
  
  1. Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, China
  
• ISSN：2095-0187

文摘

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.