Abstract
Low-molecular-weight organogels (LMOG) have been attracting a surge interest in fabricating soft materials. Although the finding of the gelator molecules has been developed from serendipity to objective design, the achievement of the gelator molecules still needs good design and tedious organic synthesis. In this paper, we proposed a simple and general mixing approach to get the organogel for nearly all the organic compounds and even soluble nanoparticles without any modification. We have designed a universal gelator molecule, which forms organogels with more than 40 kinds of organic solvents from aploar to polar solvents. More interestingly, when other organic compounds or even nanomaterials, which are soluble in certain organic solvents, are mixed with this gelator molecule, they can form organogels no matter whether the individual compounds could form organogel or not. This method is applicable to nearly all kinds of soluble organic compounds and opens an efficient and universal way to fabricate gel materials.
Similar content being viewed by others
References
Terech P, Weiss RG. Eds. Molecular Gels: Materials with Self-Assembled Fibrllar Networks. Dordrecht: Springer, 2006
Terech P, Weiss RG. Low molecular mass gelators of organic liquids and the properties of their gels. Chem Rev, 1997, 97: 3133–3159
Estroff LA, Hamilton AD. Water gelation by small organic molecules. Chem Rev, 2004, 104: 1201–1217
Mohan SRK, Hamachi I. Synthesis of new supramolecular polymers based on glycosylated amino acid and their applications. Curr Org Chem, 2005, 9: 491–502
Abdallah DJ, Weiss RG. Organogels and low molecular mass organic gelators. Adv Mater, 2000, 12: 1237–1247
Ajayaghosh A, Praveen VK. pi-organogels of self-assembled p-phenylenevinylenes: Soft materials with distinct size, shape, and functions. Acc Chem Res, 2007, 40: 644–656
Shimizu T, Masuda M, Minamikawa H. Supramolecular nanotube architectures based on amphiphilic molecules. Chem Rev, 2005, 105: 1401–1443
Hirst AR, Smith DK, Feiters MC, Geurts HPM, Wright AC. Two-component dendritic gels: Easily tunable materials. J Am Chem Soc, 2003, 125: 9010–9011
van Bommel KJC, Friggeri A, Shinkai S. Organic templates for the generation of inorganic materials. Angew Chem Int Ed, 2003, 42: 980–999
Lee KY, Mooney DJ. Hydrogels for tissue engineering. Chem Rev, 2001, 101: 1869–1879
Roy G, Miravet JF, Escuder B, Sanchez C, Llusar M. Morphology templating of nanofibrous silica through pH-sensitive gels: “in situ” and “post-diffusion” strategies. J Mater Chem, 2006, 16: 1817–1824
Gao P, Zhan CL, Liu MH. Controlled synthesis of double- and multiwall silver nanotubes with template organogel from a bolaamphiphile. Langmuir, 2006, 22: 775–779
Holmes TC, de Lacalle S, Su X, Liu GS, Rich A, Zhang SG. Extensive neurite outgrowth and active synapse formation on self-assembling peptide scaffolds. Proc Natl Acad Sci USA, 2000, 97: 6728–6733
Jung JH, 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
Hirst AR, Coates IA, Boucheteau TR, Miravet JF, Escuder B, Castelletto V, Hamley IW, Smith DK. Low-molecular-weight gelators: Elucidating the principles of gelation based on gelator solubility and a cooperative self-assembly model. J Am Chem Soc, 2008, 130: 9113–9121
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
Page MG, Warr GG. Influence of the structure and composition of mono- and dialkyl phosphate mixtures on aluminum complex organogels. Langmuir, 2009, 25: 8810–8816
Li YG, Wang TY, Liu MH. Gelating-induced supramolecular chirality of achiral porphyrins: chiroptical switch between achiral molecules and chiral assemblies. Soft Matter, 2007, 3: 1312–1317
Lal M, Pakatchi S, He GS, Kim KS, Prasad PN. Dye-doped organogels: A new medium for two-photon pumped lasing and other optical applications. Chem Mater, 1999, 11: 3012–3014
Shumburo A, Biewer MC. Stabilization of an organic photochromic material by incorporation in an organogel. Chem Mater, 2002, 14: 3745–3750
Gaponik N, Wolf A, Marx R, Lesnyak V, Schilling K, Eychmuller A. Three-dimensional self-assembly of thiol-capped CdTe nanocrystals: Gels and aerogels as building blocks for nanotechnology. Adv Mater, 2008, 20: 4257–4262
Duan PF, Li YG, Liu MH. Preparation of optical active polydiacetylene through gelating and the control of supramolecular chirality. Sci China Chem, 2010, 53: 432–437
Abdallah DJ, Weiss RG. n-alkanes gel n-alkanes (and many other organic liquids). Langmuir, 2000, 16: 352–355
George M, Snyder SL, Terech P, Glinka CJ, Weiss RG. N-alkyl perfluoroalkanamides as low molecular-mass organogelators. J Am Chem Soc, 2003, 125: 10275–10283
Abdallah DJ, Lu LD, Weiss RG. Thermoreversible organogels from alkane gelators with one heteroatom. Chem Mater, 1999, 11: 2907–2911
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
Makarevic J, Jokic M, Peric B, Tomisic V, Kojic-Prodic B, Zinic M. Bis(amino acid) oxalyl amides as ambidextrous gelators of water and organic solvents: Supramolecular gels with temperature dependent assembly/dissolution equilibrium. Chem. Eur. J., 2001, 7:3328–3341
Gronwald O, Shinkai S. Sugar-integrated gelators of organic solvents. Chem. Eur. J., 2001, 7:4328–4334
Kida T, Marui Y, Miyawaki K, Kato E, Akashi M. Unique organogel formation with a channel-type cyclodextrin assembly. Chem Commun, 2009: 3889–3891
Yagai S, Nakajima T, Kishikawa K, Kohmoto S, Karatsu T, Kitamura A. Hierarchical organization of photoresponsive hydrogen-bonded rosettes. J Am Chem Soc, 2005, 127: 11134–11139
Terech P, Ostuni E, Weiss RG. Structural study of cholesteryl anthraquinone-2-carboxylate (CAQ) physical organogels by neutron and X-ray small angle scattering. J Phys Chem, 1996, 100: 3759–3766
Ayabe M, Kishida T, Fujita N, Sada K, Shinkai S. Binary organogelators which show light and temperature responsiveness. Org Biomol Chem, 2003, 1: 2744–2747
Wang C, Zhang DQ, Xiang JF, Zhu DB. New organogels based on an anthracene derivative with one urea group and its photodimer: Fluorescence enhancement after gelation. Langmuir, 2007, 23: 9195–9200
Kamikawa Y, Kato T. Color-tunable fluorescent organogels: Columnar self-assembly of pyrene-containing oligo(glutamic acid)s. Langmuir, 2007, 23: 274–278
Burguete MI, Galindo F, Gavara R, Izquierdo MA, Lima JC, Luis SV, Parola AJ, Pina F. Use of fluorescence spectroscopy to study polymeric materials with porous structure based on imprinting by self-assembled fibrillar networks. Langmuir, 2008, 24: 9795–9803
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
Tamaru S, Uchino S, Takeuchi M, Ikeda M, Hatano T, Shinkai S. A porphyrin-based gelator assembly which is reinforced by peripheral urea groups and chirally twisted by chiral urea additives. Tetrahedron Lett, 2002, 43: 3751–3755
Tamaru S, Takeuchi M, Sano M, Shinkai S. Sol-gel transcription of sugar-appended porphyrin assemblies into fibrous silica: Unimolecular stacks versus helical bundles as templates. Angew Chem Int Ed, 2002, 41: 853–856
Diaz DD, Cid JJ, Vazquez P, Torres T. Strength enhancement of nanostructured organogels through inclusion of phthalocyanine-containing complementary organogelator structures and in situ cross-linking by click chemistry. Chem Eur J, 2008, 14: 9261–9273
Ikeda M, Takeuchi M, Shinkai S. Unusual emission properties of a triphenylene-based organogel system. Chem Commun, 2003: 1354–1355
Ziessel R, Pickaert G, Camerel F, Donnio B, Guillon D, Cesario M, Prange T. Tuning organogels and mesophases with phenanthroline Ligands and their copper complexes by inter-to intramolecular hydrogen bonds. J Am Chem Soc, 2004, 126: 12403–12413
Kishimura A, Yamashita T, Aida T. Phosphorescent organogels via “metallophilic” interactions for reversible RGB-color switching. J Am Chem Soc, 2005, 127: 179–183
Mieden-Gundert G, Klein L, Fischer M, Vogtle F, Heuze K, Pozzo JL, Vallier M, Fages F. Rational design of low molecular mass organogelators: Toward a library of functional N-acyl-1,omegaamino acid derivatives. Angew Chem Int Ed, 2001, 40: 3164–3166
Terech P, Gebel G, Ramasseul R. Molecular rods in a zinc(II) porphyrin/cyclohexane physical gel: Neutron and X-ray scattering characterizations. Langmuir, 1996, 12: 4321–4323
Kimura M, Muto T, Takimoto H, Wada K, Ohta K, Hanabusa K, Shirai H, Kobayashi N. Fibrous assemblies made of amphiphilic metallophthalocyanines. Langmuir, 2000, 16: 2078–2082
Hui JKH, Yu Z, MacLachlan MJ. Supramolecular assembly of zinc salphen complexes: Access to metal-containing gels and nanofibers. Angew Chem Int Ed, 2007, 46:7980–7983
Funkhouser GP, Tonmukayakul N, Liang F. Rheological comparison of organogelators based on iron and aluminum complexes of dodecylmethylphosphinic acid and methyl dodecanephosphonic acid. Langmuir, 2009, 25: 8672–8677
Tam AYY, Wong KMC, Yam VWW. 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, 2009, 131: 6253–6262
Ishi-i T, Shinkai S. Dye-based organogels: Stimuli-responsive soft materials based on one-dimensional self-assembling aromatic dyes. Supermol Dye Chem, 2005, 258: 119–160
Li XQ, Zhang X, Ghosh S, Wurthner F. Highly fluorescent lyotropic mesophases and organogels based on J-aggregates of core-twisted perylene bisimide dyes. Chem Eur J, 2008, 14: 8074–8078
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
Sperling LH. Introduction to Physical Polymer Science. New York: John Wiley & Sons, 2006
Davis BK. Diffusion in polymer gel implants. Proc Natl Acad Sci USA, 1974, 71: 3120–3123
Kwon IC, Bae YH, Kim SW. Electrically erodible polymer gel for controlled release of drugs. Nature, 1991, 354: 291–293
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
Yang Z, Liang G, Xu B. Enzymatic hydrogelation of small molecules. Acc Chem Res, 2008, 41: 315–326
Mueggenburg KE, Lin XM, Goldsmith RH, Jaeger HM. Elastic membranes of close-packed nanoparticle arrays. Nat Mater, 2007, 6: 656–660
Nykypanchuk D, Maye MM, van der Lelie D, Gang O. DNA-guided crystallization of colloidal nanoparticles. Nature, 2008, 451: 549–552
Petty JT, Zheng J, Hud NV, Dickson RM. DNA-templated Ag nanocluster formation. J Am Chem Soc, 2004, 126: 5207–5212
Li YG, Liu MH. Fabrication of chiral silver nanoparticles and chiral nanoparticulate film via organogel. Chem Commun, 2008: 5571-5573
Noone KM, Ginger DS. Doping for speed: Colloidal nanoparticles for thin-film optoelectronics. Acs Nano, 2009, 3: 261–265
Cassagneau T, Mallouk TE, Fendler JH. Layer-by-layer assembly of thin film zener diodes from conducting polymers and CdSe nanoparticles. J Am Chem Soc, 1998, 120: 7848–7859
Jung JH, Ono Y, Sakurai K, Sano M, Shinkai S. 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, 2000, 122: 8648–8653
Pal A, Srivastava A, Bhattacharya S. 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, 2009, 15: 9169–9182
Sangeetha NM, Bhat S, Raffy G, Belin C, Loppinet-Serani A, Aymonier C, Terech P, Maitra U, Desvergne JP, Del Guerzo A. Hybrid materials combining photoactive 2,3-didecyloxy anthracene physical gels and gold nanoparticles. Chem Mater, 2009, 21: 3424–3432
Kimura M, Kobayashi S, Kuroda T, Hanabusa K, Shirai H. Assembly of gold nanoparticles into fibrous aggregates using thiol-terminated gelators. Adv Mater, 2004, 16: 335–338
Suzuki M, Nakajima Y, Sato T, Shirai H, Hanabusa K. Fabrication of TiO2 using L-lysine-based organogelators as organic templates: control of the nanostructures. Chem Commun, 2006: 377-379
Li LS, Stupp SI. One-dimensional assembly of lipophilic inorganic nanoparticles templated by peptide-based nanofibers with binding functionalities. Angew Chem Int Ed, 2005, 44: 1833–1836
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Duan, P., Li, Y., Jiang, J. et al. Towards a universal organogelator: A general mixing approach to fabricate various organic compounds into organogels. Sci. China Chem. 54, 1051–1063 (2011). https://doi.org/10.1007/s11426-011-4295-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-011-4295-x