Towards a universal organogelator: A general mixing approach to fabricate various organic compounds into organogels

Science China Chemistry

Volumn 54, Issue 7, 2011, Pages 1051-1063

  Duan, Pengfei ^a   Li, Yuangang ^b   Jiang, Jian ^a   Wang, Tianyu ^a   Liu, Minghua ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b XI'AN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

hybrid system; organogel; self assembly; soft matter; supramolecular chemistry

Indexed keywords

GEL MATERIALS; GELATOR MOLECULES; LOW MOLECULAR WEIGHT; ORGANIC SYNTHESIS; ORGANO-GELATOR; ORGANOGEL; ORGANOGELS; POLAR SOLVENTS; SOFT MATERIAL; SOFT MATTER; SOLUBLE ORGANIC COMPOUNDS;

HYBRID MATERIALS; HYBRID SYSTEMS; MOLECULES; ORGANIC SOLVENTS; SOLVENTS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EID: 79960343350     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4295-x     Document Type: Article

References (68)

1. Terech P, Weiss RG. Eds. Molecular Gels: Materials with Self-Assembled Fibrllar Networks. Dordrecht: Springer, 2006
2. P. Terech R.G. Weiss 1997 Low molecular mass gelators of organic liquids and the properties of their gels Chem Rev 97 3133 3159 10.1021/cr9700282 1:CAS:528:DyaK2sXnsFSitLk%3D (Pubitemid 127667409)
3. L.A. Estroff A.D. Hamilton 2004 Water gelation by small organic molecules Chem Rev 104 1201 1217 10.1021/cr0302049 1:CAS:528:DC%2BD2cXhsVWks7w%3D
4. S.R.K. Mohan I. Hamachi 2005 Synthesis of new supramolecular polymers based on glycosylated amino acid and their applications Curr Org Chem 9 491 502 1:CAS:528:DC%2BD2MXhvVeju7s%3D (Pubitemid 40347620)
5. D.J. Abdallah R.G. Weiss 2000 Organogels and low molecular mass organic gelators Adv Mater 12 1237 1247 10.1002/1521-4095(200009)12:17<1237::AID- ADMA1237>3.0.CO;2-B 1:CAS:528:DC%2BD3cXnt1Wlurk%3D
6. A. Ajayaghosh V.K. Praveen 2007 pi-organogels of self-assembled p-phenylenevinylenes: Soft materials with distinct size, shape, and functions Acc Chem Res 40 644 656 10.1021/ar7000364 1:CAS:528:DC%2BD2sXltVKqur4%3D
7. T. Shimizu M. Masuda H. Minamikawa 2005 Supramolecular nanotube architectures based on amphiphilic molecules Chem Rev 105 1401 1443 10.1021/cr030072j 1:CAS:528:DC%2BD2MXisFWrtrs%3D (Pubitemid 40596869)
8. A.R. Hirst D.K. Smith M.C. Feiters H.P.M. Geurts A.C. Wright 2003 Two-component dendritic gels: Easily tunable materials J Am Chem Soc 125 9010 9011 10.1021/ja036111q 1:CAS:528:DC%2BD3sXltFKqsLY%3D (Pubitemid 36903810)
9. K.J.C. van Bommel A. Friggeri S. Shinkai 2003 Organic templates for the generation of inorganic materials Angew Chem Int Ed 42 980 999 10.1002/anie.200390284 (Pubitemid 36323415)
10. K.Y. Lee D.J. Mooney 2001 Hydrogels for tissue engineering Chem Rev 101 1869 1879 10.1021/cr000108x 1:CAS:528:DC%2BD3MXjvFSqu7w%3D (Pubitemid 35377789)
11. G. Roy J.F. Miravet B. Escuder C. Sanchez M. Llusar 2006 Morphology templating of nanofibrous silica through pH-sensitive gels: "in situ" and "post-diffusion" strategies J Mater Chem 16 1817 1824 10.1039/b601561a 1:CAS:528:DC%2BD28XktlSiurw%3D (Pubitemid 43725977)
12. P. Gao C.L. Zhan M.H. Liu 2006 Controlled synthesis of double- and multiwall silver nanotubes with template organogel from a bolaamphiphile Langmuir 22 775 779 10.1021/la0517787 1:CAS:528:DC%2BD2MXhtlajtrjO (Pubitemid 43164815)
13. T.C. Holmes S. de Lacalle X. Su G.S. Liu A. Rich S.G. Zhang 2000 Extensive neurite outgrowth and active synapse formation on self-assembling peptide scaffolds Proc Natl Acad Sci USA 97 6728 6733 10.1073/pnas.97.12.6728 1:CAS:528:DC%2BD3cXktFaitLw%3D (Pubitemid 30412782)
14. J.H. Jung G. John M. Masuda K. Yoshida S. Shinkai T. Shimizu 2001 Self-assembly of a sugar-based gelator in water: Its remarkable diversity in gelation ability and aggregate structure Langmuir 17 7229 7232 10.1021/la0109516 1:CAS:528:DC%2BD3MXnsVGitbw%3D (Pubitemid 35338200)
15. A.R. Hirst I.A. Coates T.R. Boucheteau J.F. Miravet B. Escuder V. Castelletto I.W. Hamley D.K. Smith 2008 Low-molecular-weight gelators: Elucidating the principles of gelation based on gelator solubility and a cooperative self-assembly model J Am Chem Soc 130 9113 9121 10.1021/ja801804c 1:CAS:528:DC%2BD1cXntlKrurs%3D (Pubitemid 352000851)
16. Dawn A, Fujita N, Haraguchi S, Sada K, Shinkai S. An organogel system can control the stereochemical course of anthracene photodimerization. Chem Commun, 2009: 2100-2102
17. M.G. Page G.G. Warr 2009 Influence of the structure and composition of mono- and dialkyl phosphate mixtures on aluminum complex organogels Langmuir 25 8810 8816 10.1021/la900477v 1:CAS:528:DC%2BD1MXlt1Sntr8%3D
18. Y.G. Li T.Y. Wang M.H. Liu 2007 Gelating-induced supramolecular chirality of achiral porphyrins: chiroptical switch between achiral molecules and chiral assemblies Soft Matter 3 1312 1317 10.1039/b710165a 1:CAS:528:DC%2BD2sXht1Sms7zM (Pubitemid 47630617)
19. M. Lal S. Pakatchi G.S. He K.S. Kim P.N. Prasad 1999 Dye-doped organogels: A new medium for two-photon pumped lasing and other optical applications Chem Mater 11 3012 3014 10.1021/cm990199i 1:CAS:528: DyaK1MXmtlClu7o%3D (Pubitemid 129692269)
20. A. Shumburo M.C. Biewer 2002 Stabilization of an organic photochromic material by incorporation in an organogel Chem Mater 14 3745 3750 10.1021/cm020421a 1:CAS:528:DC%2BD38Xmtlynsb8%3D
21. N. Gaponik A. Wolf R. Marx V. Lesnyak K. Schilling A. Eychmuller 2008 Three-dimensional self-assembly of thiol-capped CdTe nanocrystals: Gels and aerogels as building blocks for nanotechnology Adv Mater 20 4257 4262 10.1002/adma.200702986 1:CAS:528:DC%2BD1cXhsVOhu73K
22. P.F. Duan Y.G. Li M.H. Liu 2010 Preparation of optical active polydiacetylene through gelating and the control of supramolecular chirality Sci China Chem 53 432 437 10.1007/s11426-010-0067-2 1:CAS:528:DC%2BC3cXjsleitL8%3D
23. D.J. Abdallah R.G. Weiss 2000 n-alkanes gel n-alkanes (and many other organic liquids) Langmuir 16 352 355 10.1021/la990795r 1:CAS:528: DyaK1MXmtlKqs7Y%3D (Pubitemid 32211223)
24. M. George S.L. Snyder P. Terech C.J. Glinka R.G. Weiss 2003 N-alkyl perfluoroalkanamides as low molecular-mass organogelators J Am Chem Soc 125 10275 10283 10.1021/ja0362407 1:CAS:528:DC%2BD3sXlvFKqu7g%3D (Pubitemid 37022239)
25. D.J. Abdallah L.D. Lu R.G. Weiss 1999 Thermoreversible organogels from alkane gelators with one heteroatom Chem Mater 11 2907 2911 10.1021/cm9902826 1:CAS:528:DyaK1MXmtFWkurk%3D (Pubitemid 129692374)
26. de Loos M, Feringa BL, van Esch JH. Design and application of self-assembled low molecular weight hydrogels. Eur J Org Chem, 2005: 3615-3631 (Pubitemid 41342382)
27. J. Makarevic M. Jokic B. Peric V. Tomisic B. Kojic-Prodic M. Zinic 2001 Bis(amino acid) oxalyl amides as ambidextrous gelators of water and organic solvents: Supramolecular gels with temperature dependent assembly/dissolution equilibrium Chem. Eur. J. 7 3328 3341 10.1002/1521-3765(20010803)7:15<3328:: AID-CHEM3328>3.0.CO;2-C 1:CAS:528:DC%2BD3MXmtVCksLg%3D (Pubitemid 32777235)
28. O. Gronwald S. Shinkai 2001 Sugar-integrated gelators of organic solvents Chem. Eur. J. 7 4328 4334 10.1002/1521-3765(20011015)7:20<4328::AID- CHEM4328>3.0.CO;2-S 1:STN:280:DC%2BD3MnktlWnuw%3D%3D (Pubitemid 33000549)
29. Kida T, Marui Y, Miyawaki K, Kato E, Akashi M. Unique organogel formation with a channel-type cyclodextrin assembly. Chem Commun, 2009: 3889-3891
30. S. Yagai T. Nakajima K. Kishikawa S. Kohmoto T. Karatsu A. Kitamura 2005 Hierarchical organization of photoresponsive hydrogen-bonded rosettes J Am Chem Soc 127 11134 11139 10.1021/ja052645a 1:CAS:528:DC%2BD2MXmtV2ltLg%3D (Pubitemid 41129890)
31. P. Terech E. Ostuni R.G. Weiss 1996 Structural study of cholesteryl anthraquinone-2-carboxylate (CAQ) physical organogels by neutron and X-ray small angle scattering J Phys Chem 100 3759 3766 10.1021/jp952735+ 1:CAS:528:DyaK28Xpt1Wktw%3D%3D (Pubitemid 126788394)
32. M. Ayabe T. Kishida N. Fujita K. Sada S. Shinkai 2003 Binary organogelators which show light and temperature responsiveness Org Biomol Chem 1 2744 2747 10.1039/b304224c 1:CAS:528:DC%2BD3sXlsleks7g%3D
33. C. Wang D.Q. Zhang J.F. Xiang D.B. Zhu 2007 New organogels based on an anthracene derivative with one urea group and its photodimer: Fluorescence enhancement after gelation Langmuir 23 9195 9200 10.1021/la701142d 1:CAS:528:DC%2BD2sXns1OhtL4%3D (Pubitemid 47383506)
34. Y. Kamikawa T. Kato 2007 Color-tunable fluorescent organogels: Columnar self-assembly of pyrene-containing oligo(glutamic acid)s Langmuir 23 274 278 10.1021/la061581u 1:CAS:528:DC%2BD28XosVylt7g%3D (Pubitemid 46129733)
35. M.I. Burguete F. Galindo R. Gavara M.A. Izquierdo J.C. Lima S.V. Luis A.J. Parola F. Pina 2008 Use of fluorescence spectroscopy to study polymeric materials with porous structure based on imprinting by self-assembled fibrillar networks Langmuir 24 9795 9803 10.1021/la801342f 1:CAS:528:DC%2BD1cXpsVGrtrg%3D
36. Yang XC, Lu R, Xu TH, Xue PC, Liu XL, Zhao YY. Novel carbazole-based organogels modulated by tert-butyl moieties. Chem Commun, 2008: 453-455
37. S. Tamaru S. Uchino M. Takeuchi M. Ikeda T. Hatano S. Shinkai 2002 A porphyrin-based gelator assembly which is reinforced by peripheral urea groups and chirally twisted by chiral urea additives Tetrahedron Lett 43 3751 3755 10.1016/S0040-4039(02)00541-5 1:CAS:528:DC%2BD38Xjt1Cku74%3D (Pubitemid 34461878)
38. S. Tamaru M. Takeuchi M. Sano S. Shinkai 2002 Sol-gel transcription of sugar-appended porphyrin assemblies into fibrous silica: Unimolecular stacks versus helical bundles as templates Angew Chem Int Ed 41 853 856 10.1002/1521-3773(20020301)41:5<853::AID-ANIE853>3.0.CO;2-R 1:CAS:528:DC%2BD38XisVahsb0%3D (Pubitemid 34218545)
39. D.D. Diaz J.J. Cid P. Vazquez T. Torres 2008 Strength enhancement of nanostructured organogels through inclusion of phthalocyanine-containing complementary organogelator structures and in situ cross-linking by click chemistry Chem Eur J 14 9261 9273 10.1002/chem.200800714 1:CAS:528: DC%2BD1cXhtlKgtrbF
40. Ikeda M, Takeuchi M, Shinkai S. Unusual emission properties of a triphenylene-based organogel system. Chem Commun, 2003: 1354-1355 (Pubitemid 36734926)
41. R. Ziessel G. Pickaert F. Camerel B. Donnio D. Guillon M. Cesario T. Prange 2004 Tuning organogels and mesophases with phenanthroline Ligands and their copper complexes by inter-to intramolecular hydrogen bonds J Am Chem Soc 126 12403 12413 10.1021/ja047091a 1:CAS:528:DC%2BD2cXnsVaisbk%3D (Pubitemid 39304922)
42. A. Kishimura T. Yamashita T. Aida 2005 Phosphorescent organogels via "metallophilic" interactions for reversible RGB-color switching J Am Chem Soc 127 179 183 10.1021/ja0441007 1:CAS:528:DC%2BD2cXhtVyltr7L (Pubitemid 40094382)
43. G. Mieden-Gundert L. Klein M. Fischer F. Vogtle K. Heuze J.L. Pozzo M. Vallier F. Fages 2001 Rational design of low molecular mass organogelators: Toward a library of functional N-acyl-1,omegaamino acid derivatives Angew Chem Int Ed 40 3164 3166 10.1002/1521-3773(20010903)40:17<3164::AID-ANIE3164>3. 0.CO;2-B 1:CAS:528:DC%2BD3MXmvVyitL8%3D (Pubitemid 32845383)
44. P. Terech G. Gebel R. Ramasseul 1996 Molecular rods in a zinc(II) porphyrin/cyclohexane physical gel: Neutron and X-ray scattering characterizations Langmuir 12 4321 4323 10.1021/la960381n 1:CAS:528: DyaK28XkvVyqtb8%3D (Pubitemid 126536444)
45. M. Kimura T. Muto H. Takimoto K. Wada K. Ohta K. Hanabusa H. Shirai N. Kobayashi 2000 Fibrous assemblies made of amphiphilic metallophthalocyanines Langmuir 16 2078 2082 10.1021/la990801j 1:CAS:528:DC%2BD3cXosFensQ%3D%3D (Pubitemid 30572989)
46. J.K.H. Hui Z. Yu M.J. MacLachlan 2007 Supramolecular assembly of zinc salphen complexes: Access to metal-containing gels and nanofibers Angew Chem Int Ed 46 7980 7983 10.1002/anie.200702680 1:CAS:528:DC%2BD2sXht1KitL7J (Pubitemid 350033471)
47. G.P. Funkhouser N. Tonmukayakul F. Liang 2009 Rheological comparison of organogelators based on iron and aluminum complexes of dodecylmethylphosphinic acid and methyl dodecanephosphonic acid Langmuir 25 8672 8677 10.1021/la8043329 1:CAS:528:DC%2BD1MXjvVehsb8%3D
48. A.Y.Y. Tam K.M.C. Wong V.W.W. Yam 2009 Unusual luminescence enhancement of metallogels of alkynylplatinum(II) 2,6-bis(N-alkylbenzimidazol-2′-yl) pyridine complexes upon a gel-to-sol phase transition at elevated temperatures J Am Chem Soc 131 6253 6262 10.1021/ja900895x 1:CAS:528:DC%2BD1MXktF2gtLs%3D
49. T. Ishi-i S. Shinkai 2005 Dye-based organogels: Stimuli-responsive soft materials based on one-dimensional self-assembling aromatic dyes Supermol Dye Chem 258 119 160 10.1007/b135554 1:CAS:528:DC%2BD2MXhtlCltb7N (Pubitemid 44420806)
50. X.Q. Li X. Zhang S. Ghosh F. Wurthner 2008 Highly fluorescent lyotropic mesophases and organogels based on J-aggregates of core-twisted perylene bisimide dyes Chem Eur J 14 8074 8078 10.1002/chem.200800915 1:CAS:528:DC%2BD1cXht1Gnt7vM
51. Tian HJ, Inoue K, Yoza K, Ishi-i T, Shinkai S. New organic gelalors bearing a porphyrin group: A new strategy to create ordered porphyrin assemblies. Chem Lett, 1998: 871-872
52. Sperling LH. Introduction to Physical Polymer Science. New York: John Wiley & Sons, 2006
53. B.K. Davis 1974 Diffusion in polymer gel implants Proc Natl Acad Sci USA 71 3120 3123 10.1073/pnas.71.8.3120 1:CAS:528:DyaE2MXitFOqsg%3D%3D
54. I.C. Kwon Y.H. Bae S.W. Kim 1991 Electrically erodible polymer gel for controlled release of drugs Nature 354 291 293 10.1038/354291a0 1:CAS:528:DyaK38Xks1Wmsw%3D%3D (Pubitemid 21896877)
55. Wang P, Zakeeruddin SM, Exnar I, Gratzel M. High efficiency dye-sensitized nanocrystalline solar cells based on ionic liquid polymer gel electrolyte. Chem Commun, 2002: 2972-2973 (Pubitemid 36044143)
56. Z. Yang G. Liang B. Xu 2008 Enzymatic hydrogelation of small molecules Acc Chem Res 41 315 326 10.1021/ar7001914 1:CAS:528:DC%2BD1cXoslyitQ%3D%3D
57. K.E. Mueggenburg X.M. Lin R.H. Goldsmith H.M. Jaeger 2007 Elastic membranes of close-packed nanoparticle arrays Nat Mater 6 656 660 10.1038/nmat1965 1:CAS:528:DC%2BD2sXpvFKjsr0%3D (Pubitemid 47359548)
58. D. Nykypanchuk M.M. Maye D. van der Lelie O. Gang 2008 DNA-guided crystallization of colloidal nanoparticles Nature 451 549 552 10.1038/nature06560 1:CAS:528:DC%2BD1cXhs1ent7s%3D (Pubitemid 351186275)
59. J.T. Petty J. Zheng N.V. Hud R.M. Dickson 2004 DNA-templated Ag nanocluster formation J Am Chem Soc 126 5207 5212 10.1021/ja031931o 1:CAS:528:DC%2BD2cXis1Oru7g%3D (Pubitemid 38509476)
60. Li YG, Liu MH. Fabrication of chiral silver nanoparticles and chiral nanoparticulate film via organogel. Chem Commun, 2008: 5571-5573
61. K.M. Noone D.S. Ginger 2009 Doping for speed: Colloidal nanoparticles for thin-film optoelectronics Acs Nano 3 261 265 10.1021/nn9000935 1:CAS:528:DC%2BD1MXhsFegsb0%3D
62. T. Cassagneau T.E. Mallouk J.H. Fendler 1998 Layer-by-layer assembly of thin film zener diodes from conducting polymers and CdSe nanoparticles J Am Chem Soc 120 7848 7859 10.1021/ja9806027 1:CAS:528:DyaK1cXkvFKltrg%3D (Pubitemid 28392067)
63. J.H. Jung Y. Ono K. Sakurai M. Sano S. Shinkai 2000 Novel vesicular aggregates of crown-appended cholesterol derivatives which act as gelators of organic solvents and as templates for silica transcription J Am Chem Soc 122 8648 8653 10.1021/ja001623f 1:CAS:528:DC%2BD3cXlvFOqtr8%3D
64. A. Pal A. Srivastava S. Bhattacharya 2009 Role of capping ligands on the nanoparticles in the modulation of properties of a hybrid matrix of nanoparticles in a 2D film and in a supramolecular organogel Chem Eur J 15 9169 9182 10.1002/chem.200900304 1:CAS:528:DC%2BD1MXhtV2qs7%2FN
65. N.M. Sangeetha S. Bhat G. Raffy C. Belin A. Loppinet-Serani C. Aymonier P. Terech U. Maitra J.P. Desvergne A. Del Guerzo 2009 Hybrid materials combining photoactive 2,3-didecyloxy anthracene physical gels and gold nanoparticles Chem Mater 21 3424 3432 10.1021/cm901225s 1:CAS:528:DC%2BD1MXotFKntrc%3D
66. M. Kimura S. Kobayashi T. Kuroda K. Hanabusa H. Shirai 2004 Assembly of gold nanoparticles into fibrous aggregates using thiol-terminated gelators Adv Mater 16 335 338 10.1002/adma.200305804 1:CAS:528:DC%2BD2cXisVansrg%3D
67. 2 using L-lysine-based organogelators as organic templates: control of the nanostructures. Chem Commun, 2006: 377-379
68. L.S. Li S.I. Stupp 2005 One-dimensional assembly of lipophilic inorganic nanoparticles templated by peptide-based nanofibers with binding functionalities Angew Chem Int Ed 44 1833 1836 10.1002/anie.200462142 1:CAS:528: DC%2BD2MXislWkurg%3D