Versatile supramolecular gelators that can harden water, organic solvents and ionic liquids

Langmuir

Volumn 28, Issue 25, 2012, Pages 9259-9266

  Minakuchi, Nami ^a   Hoe, Kazuki ^a   Yamaki, Daisuke ^a   Ten No, Seiichiro ^a   Nakashima, Kazunori ^a   Goto, Masahiro ^b   Mizuhata, Minoru ^a   Maruyama, Tatsuo ^a  

^a KOBE UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY CALCULATIONS; EDIBLE OIL; ELECTROCHEMICAL APPLICATIONS; GELATOR MOLECULES; GELATORS; GLUCONIC ACIDS; HIGH TEMPERATURE; HYDROPHOBIC TAILS; LIQUID-PHASE SYNTHESIS; MICROSCOPIC OBSERVATIONS; MOLECULAR PACKINGS; SELF-ASSEMBLED; SMALL ANGLE X-RAY SCATTERING; SUPRAMOLECULAR GELATORS; WIDE PH RANGE;

AMINO ACIDS; COAGULATION; DENSITY FUNCTIONAL THEORY; GELATION; NANOFIBERS; ORGANIC SOLVENTS; SOLVENTS; SUPRAMOLECULAR CHEMISTRY;

IONIC LIQUIDS;

EID: 84862845384     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la301442f     Document Type: Article

References (43)

1. Frkanec, L.; Jokic, M.; Makarevic, J.; Wolsperger, K.; Zinic, M. Bis(PheOH) maleic acid amide-fumaric acid amide photoizomerization induces microsphere-to-gel fiber morphological transition: The photoinduced gelation system J. Am. Chem. Soc. 2002, 124, 9716-9717
2. van Bommel, K. J. C.; van der Pol, C.; Muizebelt, I.; Friggeri, A.; Herees, A.; Meetsma, A.; Feringa, B. L.; van Esch, J. H. Responsive cyclohexane-based low-molecular-weight hydrogelators with modular architecture Angew. Chem., Int. Ed. 2004, 43, 1663-1667 (Pubitemid 39257857)
3. Krieg, E.; Shirman, E.; Weissman, H.; Shimoni, E.; Wolf, S. G.; Pinkas, I.; Rybtchinski, B. Supramolecular gel based on a perylene diimide dye: multiple stimuli responsiveness, robustness, and photofunction J. Am. Chem. Soc. 2009, 131, 14365-14373
4. Komatsu, H.; Matsumoto, S.; Tamaru, S.; Kaneko, K.; Ikeda, M.; Hamachi, I. Supramolecular hydrogel exhibiting four basic logic gate functions to fine-tune substance release J. Am. Chem. Soc. 2009, 131, 5580-5585
5. Koda, D.; Maruyama, T.; Minakuchi, N.; Nakashima, K.; Goto, M. Proteinase-mediated drastic morphological change of peptide-amphiphile to induce supramolecular hydrogelation Chem. Commun. 2010, 46, 979-981
6. Lu, L.; Weiss, R. G. Cholestanyl substituted quaternary ammonium salts as gelators of organic liquids Langmuir 1995, 11, 3630-3632
7. Wang, G.; Cheuk, S.; Yang, H.; Goyal, N.; Reddy, P. V. N.; Hopkinson, B. Synthesis and characterization of monosaccharide-derived carbamates as low-molecular-weight gelators Langmuir 2009, 25, 8696-8705
8. Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Self-assembly and mineralization of peptide-amphiphile nanofibers Science 2001, 294, 1684-1687
9. Matson, J. B.; Zha, R. H.; Stupp, S. I. Peptide self-assembly for crafting functional biological materials Curr. Opin. Solid State Mater. Sci. 2011, 15, 225-235
10. Sone, E. D.; Stupp, S. I. Bio-inspired magnetite mineralization of peptide-amphiphile nanofibers Chem. Mater. 2011, 23, 2005-2007
11. Jung, J. H.; John, G.; Masuda, M.; Yoshida, K.; Shinkai, S.; Shimizu, T. Self-assembly of a sugar-based gelator in water: Its remarkable diversity in gelation ability and aggregate structure Langmuir 2001, 17, 7229-7232 (Pubitemid 35338200)
12. Vemula, P. K.; John, G. Smart amphiphiles: Hydro/organogelators for in situ reduction of gold Chem. Commun. 2006, 21, 2218-2220 (Pubitemid 43800879)
13. Yan, N.; He, G.; Zhang, H.; Ding, L.; Fang, Y. Glucose-based fluorescent low-molecular mass compounds: creation of simple and versatile supramolecular gelators Langmuir 2009, 26, 5909-5917
14. Imura, Y.; Matsue, K.; Sugimoto, H.; Ito, R.; Kondo, T.; Kawai, T. Ambidextrous gel property and pH-responsive sol-gel transition of low molecular mass gelator based on a long-chain amide derivative Chem. Lett. 2009, 38, 778-779
15. Kar, T.; Debnath, S.; Das, D.; Shome, A.; Das, P. K. Organogelation and hydrogelation of low-molecular-weight amphiphilic dipeptides: pH responsiveness in phase-selective gelation and dye removal Langmuir 2009, 25, 8639-8648
16. Suzuki, M; Nakajima, Y; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. Effects of hydrogen bonding and van der Waals interactions on organogelation using designed low-molecular-weight gelators and gel formation at room temperature Langmuir 2003, 19, 8622-8624
17. Suzuki, M.; Sato, T.; Shirai, H.; Hanabusa, K. Powerful low-molecular-weight gelators based on l -valine and l -isoleucine with various terminal groups New J. Chem. 2006, 30, 1184-1191 (Pubitemid 44174318)
18. Suzuki, M.; Saito, H.; Shirai, H.; Hanabusa, K. Supramolecular organogel formation triggered by acid-base interaction in two-component system consisting of l -lysine derivative and aliphatic acids New J. Chem. 2007, 31, 1654-1660 (Pubitemid 47330718)
19. Das, D.; Dasgupta, A.; Roy, S.; Mitra, R. N.; Debnath, S.; Das, P. K. Water gelation of an amino acid-based amphiphile Chem.-Eur. J. 2006, 12, 5068-5074 (Pubitemid 43999127)
20. Yang, Z.; Liang, G.; Wang, L.; Xu, B. Using a kinase/phosphatase switch to regulate a supramolecular hydrogel and forming the supramoleclar hydrogel in vivo J. Am. Chem. Soc. 2006, 128, 3038-3043
21. Yang, Z. M.; Xu, K. M.; Guo, Z. F.; Guo, Z. H.; Xu, B. Intracellular enzymatic formation of nanofibers results in hydrogelation and regulated cell death Adv. Mater. 2007, 19, 3152-3156 (Pubitemid 350044452)
22. Zhang, Y.; Gu, H. W.; Yang, Z. M.; Xu, B. Supramolecular hydrogels respond to ligand-receptor interaction J. Am. Chem. Soc. 2003, 125, 13680-13681 (Pubitemid 37386040)
23. Kimizuka, N.; Nakashima, T. Spontaneous self-assembly of glycolipid bilayer membranes in sugar-philic ionic liquids and formation of ionogels Langmuir 2001, 17, 6759-6761 (Pubitemid 35330554)
24. Nakashima, T.; Kimizuka, N. Vesicles in salt: Formation of bilayer membranes from dialkyldimethylammonium bromides in ether-containing ionic liquids Chem. Lett. 2002, 31, 1018-1019 (Pubitemid 36057244)
25. Kubo, W.; Kitamura, T.; Hanabusa, K.; Wada, Y.; Yanagida, S. Quasi-solid-state dye-sensitized solar cells using room temperature molten salts and a low molecular weight gelator Chem. Commun. 2002, 374-375 (Pubitemid 34177734)
26. Hanabusa, K.; Fukui, H.; Suzuki, M.; Shirai, H. Specialist gelator for ionic liquids Langmuir 2005, 21, 10383-10390 (Pubitemid 41692110)
27. Mohmeyer, N.; Kuang, D.; Wang, P.; Schmidt, H. W.; Zakeeruddin, S. M.; Gratzel, M. An efficient organogelator for ionic liquids to prepare stable quasi-solid-state dye-sensitized solar cells J. Mater. Chem. 2006, 16, 2978-2983 (Pubitemid 44087252)
28. Tan, L.; Dong, X.; Wang, H.; Yang, Y. Gels of ionic liquid [ C 4 mim ]PF6 formed by self-assembly of gelators and their electrochemical properties Electrochem. Commun. 2009, 11, 933-936
29. Dutta, S.; Das, D.; Dasgupta, A.; Das, P. K. Amino acid based low-molecular-weight ionogels as efficient dye-adsorbing agents and templates for the synthesis of TiO(2) nanoparticles Chem.-Eur. J. 2010, 16, 1493-1505
30. Dong, X. L.; Wang, H.; Fang, F.; Li, X.; Yang, Y. J. Effect of gelator structures on electrochemical properties of ionic-liquid supramolecular gel electrolytes Electrochim. Acta 2010, 55, 2275-2279
31. Cai, M. R.; Liang, Y. M; Zhou, F; Liu, W. M. Functional ionic gels formed by supramolecular assembly of a novel low molecular weight anticorrosive/ antioxidative gelator J. Mater. Chem. 2011, 21, 13399-13405
32. Ionic Liquids: From Knowledge to Application Plechkova, N. V.; Rogers, R. D.; Seddon, K. R., Eds.; Oxford University Press: Oxford, 2010.
33. Park, S.; Kazlauskas, R. J. Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations J. Org. Chem. 2001, 66, 8395-8401 (Pubitemid 34002932)
34. Borges, A. R.; Hyacinth, M.; Lum, M.; Dingle, C. M.; Hamilton, P. L.; Chruszcz, M.; Pu, L.; Sabat, M.; Caran, K. L. Self-assembled thermoreversible gels of nonpolar liquids by racemic propargylic alcohols with fluorinated and nonfluorinated aromatic rings Langmuir 2008, 24, 7421-7431
35. Suzuki, M.; Owa, S.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. New l -valine-based hydrogelators: Formation of supramolecular hydrogels Tetrahedron Lett. 2004, 45, 5399-5402 (Pubitemid 38781864)
36. Kiyonaka, S.; Sada, K.; Yoshimura, I.; Shinkai, S.; Kato, N.; Hamachi, I. Semi-wet peptide/protein array using supramolecular hydrogel Nat. Mater. 2004, 3, 58-64
37. Zhou, S.-L.; Matsumoto, S.; Tian, H.-D.; Yamane, H.; Ojida, A.; Kiyonaka, S.; Hamachi, I. pH-Responsive shrinkage/swelling of a supramolecular hydrogel composed of two small amphiphilic molecules Chem.-Eur. J. 2005, 11, 1130-136 (Pubitemid 40299265)
38. Pasc, A.; Gizzi, P.; Dupuy, N.; Parant, S.; Ghanbaja, J.; Gérardin, C. Microscopic and macroscopic anisotropy in supramolecular hydrogels of histidine-based surfactants Tetrahedron Lett. 2009, 50, 6183-6186
39. Imae, T.; Hayashi, N.; Matsumoto, T.; Tada, T.; Furusaka, M. Structures of fibrous Supramolecular assemblies constructed by amino acid surfactants: investigation by AFM, SANS, and SAXS J. Colloid Interface Sci. 2000, 225, 285-290 (Pubitemid 30313904)
40. Jeong, Y.; Hanabusa, K.; Masunaga, H.; Akiba, I.; Miyoshi, K.; Sakurai, S.; Sakurai, S, K. Solvent/gelator interactions and supramolecular structure of gel fibers in cyclic bis-urea/primary alcohol organogels Langmuir 2005, 21, 586-594 (Pubitemid 40168843)
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J., Gaussian 09 (Revision A.02); Gaussian, Inc.: Wallingford CT, 2009.
42. Susan, M. A. B. H.; Kaneko, T.; Noda, A.; Watanabe, M. Ion gels prepared by in situ radical polymerization of vinyl monomers in an ionic liquid and their characterization as polymer electrolytes J. Am. Chem. Soc. 2005, 127, 4976-4983
43. Bonhote, P.; Dias, A. P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Hydrophobic, highly conductive ambient-temperature molten salts Inorg. Chem. 1996, 35, 1168-1178 (Pubitemid 126460673)