An instant-formative heat-set organogel induced by small organic molecules at a high temperature

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 421, Issue , 2013, Pages 44-50

  Xing, Pengyao ^a   Sun, Tao ^a   Li, Shangyang ^a   Hao, Aiyou ^a   Su, Jie ^a   Hou, Yuehui ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

High temperature; Instant formation; Oranogel; Small organic molecules; cyclodextrin

Indexed keywords

CHLORINE COMPOUNDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FUNCTIONAL GROUPS; HYDROGEN BONDS; KETONES; LITHIUM; MOLECULAR DYNAMICS; SCANNING ELECTRON MICROSCOPY; X RAY DIFFRACTION;

ALKYL CHAIN; GEL PHASE; HIGH TEMPERATURE; INSTANT-FORMATION; INTERMOLECULAR HYDROGEN BONDS; LITHIUM CHLORIDE; MICROMORPHOLOGIES; MOLECULAR DYNAMICS SIMULATIONS; NOVEL APPLICATIONS; ORANOGEL; ORGANOGELS; SELF-ASSEMBLED; SMALL ORGANIC MOLECULES;

MOLECULES;

4 METHYL 2 PENTANONE; ACETIC ACID; ACETIC ANHYDRIDE; ADIPIC ACID; ALCOHOL; ALIPHATIC COMPOUND; BENZALDEHYDE; BETA CYCLODEXTRIN; BUTYRALDEHYDE; CITRIC ACID; CYCLOHEXYLAMINE; DIETHYLENETRIAMINE; FORMIC ACID; FUNCTIONAL GROUP; ISOBUTYRIC ACID; KETONE; LACTIC ACID; LITHIUM CHLORIDE; LYSINE; N,N DIMETHYLACETAMIDE; OCTADECANOL; OCTADECYLAMINE; OLEIC ACID; ORGANIC COMPOUND; OXALIC ACID; PHOSPHORIC ACID; PYRIDINE; SUCCINIC ACID; TARTARIC ACID; TRIBUTYLAMINE;

ARTICLE; GEL; GELATION; HIGH TEMPERATURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MICROMORPHOLOGY; MOLECULAR DYNAMICS; ORGANOGEL; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; SOLUTION AND SOLUBILITY; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION;

EID: 84873032122     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2012.12.052     Document Type: Article

References (41)

1. Terech P., Weiss R.G. Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev. 1997, 97:3133.
2. Araki K., Yoshikawa I. Nucleobase-containing gelators. Top. Curr. Chem. 2005, 256:133.
3. Basit H., Pal A., Sen S., Bhattacharya S. Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles. Chem. Eur. J. 2008, 14:6534.
4. Yang Z.M., Liang G.L., Xu B. Supramolecular hydrogels based on β-amino acid derivatives. Chem. Commun. 2006, 7:738.
5. Kimura M., Muto T., Takimoto H., et al. Fibrous assemblies made of amphiphilic metallophthalocyanines. Langmuir 2000, 16:2078.
6. Sangeetha N.M., Maitra U. Supramolecular gels: functions and uses. Chem. Soc. Rev. 2005, 34:821.
7. Jonathan W.S. Supramolecular gel chemistry: developments over the last decade. Chem. Commun. 2011, 47:1379.
8. Piepenbrock M.M., Lioyd G.O., Clarke N., Steed J.W. Metal- and anion-binding supramolecular gels. Chem. Rev. 2010, 110:1960.
9. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 1998, 98:2045.
10. Deng W., D.H Thompson, pH and cation-responsive supramolecular gels formed by cyclodextrin amines in DMSO. Chem. Commun. 2010, 6:1884.
11. Kida T., Marui Y., Miyawaki K., Kato E., Akashi M. Unique organogel formation with a channel-type cyclodextrin assembly. Chem. Commun. 2009, 26:3889.
12. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 1998, 98:1743.
13. Deng W., Yamaguchi H., Takashima Y., Harada A. A chemical-responsive supramolecular hydrogel from modified cyclodextrins. Angew. Chem. Int. Ed. 2007, 46:5114.
14. Rango C., Charpin P., Navaza J., Keller N., Nicalis I., F, Villain, Coleman W.A. Beta-cyclodextrin/pyridine gel systems. The crystal structure of a firstbeta-cyclodextrin-pyridine water compound. J. Am. Chem. Soc. 1992, 114:5475.
15. Rizkov D., Mizrahi S., Gun J., Hoffman R., Melman A., Lev O. Nonstoichiometric gelation of cyclodextrins and included planar guests. Langmuir 2008, 24:11902.
16. Yang Z., Liang G., Xu B. Enzymatic hydrogelation of small molecules. Acc. Chem. Res. 2008, 41:315.
17. Maeda H. Anion-responsive supramolecular gels. Chem. Eur. J. 2008, 14:11274.
18. Foster J.A., Steed J.W. Exploiting cavities in supramolecular gels. Angew. Chem. Int. Ed. 2010, 49:6718.
19. Wu H.X., Ni B.B., Wang C., Zhai F., Ma Y.G. Acid-responsive organogel mediated by arene-perfluoroarene and hydrogen bonding interactions. Soft Matter 2012, 8:5486.
20. Jiang L.X., Yan Y., Huang J.B. Aqueous self-assembly of SDS@2β-CD complexes: lamellae and vesicles. Soft Matter 2011, 7:10417.
21. Edwards W., Smith D.K. Cation-responsive silver-selective organogel - exploiting silver-alkene interactions in the gel-phase. Chem. Commun. 2012, 48:2767.
22. Yajima S., Takami K., Ooue R., Kimura K. Remarkable potassium selectivity of ion sensors based on supramolecular gel membranes made from low-molecular-weight gelators without any ionophore. Analyst 2011, 136:5131.
23. Ayabe M., Kishida T., Fujita N., Sada K., Shinkai S. Binary organogelators which show light and temperature responsiveness. Org. Biomol. Chem. 2003, 1:2744.
24. Naota T., Koori H. Molecules that assemble by sound: an application to the instant gelation of stable organic fluids. J. Am. Chem. Soc. 2005, 127:9324.
25. Dong S., Luo Y., Yan X., Zheng B., Ding X., Yu Y., Ma Z., Zhao Q., Huang F. A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition. Angew. Chem. Int. Ed. 2011, 50:1905.
26. Buhler G., Feiters M.C., Nolte R.J.M., Dotz K.H. A metal-carbene carbohydrate amphiphile as a low-molecular-mass organometallic gelator. Angew. Chem. Int. Ed. 2003, 42:2494.
27. Zhang S., Greenfield M.A., Mata A., Palmer L.C., Bitton R., Mantei J.R., Aparicio C., Cruz M.O., Stupp S.I. A self-assembly pathway to aligned monodomain gels. Nat. Mat. 2010, 9:594.
28. Hirst A.R., Escuder B., Miravet J.F., Smith D.K. High-tech applications of self-assembling supra-molecular nanostructured gel-phase materials: from regenerative medicine to electronic devices. Angew. Chem. Int. Ed. 2008, 47:8002.
29. Wang Y., Tang L., Yu J. Investigation of spontaneous transition from low-molecular-weight hydrogel into macroscopic crystals. Cryst. Growth Des. 2008, 8:884.
30. Li Y.Y., et al. Reversible heat-set organogel based on supramolecular interactions of β-cyclodextrin in N,N-dimethylformamide. J. Phys. Chem. B 2010, 114:10321.
31. Jeong Y., Hanabusa K., Masunaga H., Akiba I., Miyoshi K., Sakurai S., Sakurai K. Solvent/gelator interactions and supramolecular structure of gel fibers in cyclic bis-urea/primary alcohol organogels. Langmuir 2005, 21:586-594.
32. Hirst A.R., Smith D.K. Solvent effects on supramolecular gel-phase materials: two-component dendritic gel. Langmuir 2004, 20:10851-10857.
33. Weng W., Li Z., Jamieson A.M., Rowan S.J. Control of gel morphology and properties of a class of metallo-supramolecular polymers by good/poor solvent environments. Macromolecules 2009, 42:236-246.
34. Nostro P.L., Santoni I., Bonini M., Baglioni P. Inclusion compound from a semifluorinated alkane and β-cyclodextrin. Langmuir 2003, 19:2313.
35. Saenger W., Jacob J., Gessler K., Steiner T., Hoffmann D., Sanbe H., Koizumi K., Smith S.M., Takaha T. Structures of the common cyclodextrins and their larger analogue - beyond the doughnut. Chem. Rev. 1998, 98:1787.
36. Jiao H., Goh S.H., Valiyaveettil S., Zheng J.W. Inclusion complexes of perfluorinated oligomers with cyclodextrins. Macromolecules 2003, 36:4241.
37. Liu L., Zhu S. A study on the supramolecular structure of inclusion complex of β-cyclodextrin with prazosin hydrochloride. Carbohydr. Polym. 2007, 68:472.
38. Gao A.Y., Zhao X.Y., Dong B., Zheng L.Q., Li N., Zhang S.H. Inclusion complexes of β-cyclodextrin with ionic liquid surfactants. J. Phys. Chem. B 2006, 110:8576.
39. Freedman H.H. Intramolecular H-bonds. I. A spectroscopic study of the hydrogen bond between hydroxyl and nitrogen. J. Am. Chem. Soc. 1961, 83:2900.
40. Nishiyabu R., Kano K. Double self-inclusion by rotating glucopyranose units in per-O-methylated β-cyclodextrin moieties attached to a porphyrin in aqueous solution. Eur. J. Org. Chem. 2004, 24:1985.
41. Kano K., Tanaka N., Minamizono H., Kawakita Y. Tetraarylporphyrins as probes for studying mechanism of inclusion-complex formation of cyclodextrins. Effect of microscopic environment on inclusion of ionic guests. Chem. Lett. 1996, 11:925.