Supramolecular gelling agents: can they be designed?

The last two decades have witnessed an upsurge of research activities in the area of supramolecular gelators, especially low molecular mass organic gelators (LMOGs), not only for academic interests but also for their potential applications in materials science. However, most of the gelators are serendipitously obtained; their rational design and synthesis is still a major challenge. Wide structural diversities of the molecules known to act as LMOGs and a dearth of molecular level understanding of gelation mechanisms make it difficult to pin-point a particular strategy to achieve rational design of gelators. Nevertheless, some efforts are being made to achieve this goal. Once a gelling agent is serendipitously obtained, new gelling agents with novel properties may be prepared by modifying the parent gelator molecule following a molecular engineering rationale; however, such approach is limited to the same class of gelling agent generated from the parent gelating scaffold. A crystal engineering approach wherein the single-crystal structure of a molecule is correlated with its gelling/nongelling behaviour (structure-property correlation) allows molecular level understandings of the self-assembly of the gelator and nongelator molecules and therefore, provides new insights into the design aspects of supramolecular gelling agents. This tutorial review aims at highlighting some of the developments covering both molecular and crystal engineering approaches in designing LMOGs.

[1]  M. Ikeda,et al.  [60]Fullerene Can Reinforce the Organogel Structure of Porphyrin-Appended Cholesterol Derivatives: Novel Odd−Even Effect of the (CH2)n Spacer on the Organogel Stability , 2001 .

[2]  K. Hanabusa,et al.  Cyclo(dipeptide)s as low-molecular-mass gelling agents to harden organic fluids , 1994 .

[3]  P. Dastidar,et al.  Structural studies of a new low molecular mass organic gelator for organic liquids based on simple salt , 2003 .

[4]  David K. Smith,et al.  Supramolecular dendritic two-component gel , 2001 .

[5]  Richard G. Weiss,et al.  Molecular Gels: Materials with Self-Assembled Fibrillar Networks , 2005 .

[6]  C. Brown,et al.  The crystal structure of terephthalic acid , 1967 .

[7]  R. Mukkamala,et al.  Anthraquinone–steroid based gelators of alcohols and alkanes , 1995 .

[8]  P. Dastidar,et al.  Supramolecular hydrogen bond isomerism in organic salts : A transition from 0D to 1D , 2006 .

[9]  M. Nishio CH/π hydrogen bonds in crystals , 2004 .

[10]  Xu,et al.  The Gelation of CO(2): A Sustainable Route to the Creation of Microcellular Materials. , 1999, Science.

[11]  K. Hanabusa,et al.  Excellent gelators for organic fluids: Simple bolaform amides derived from amino acids , 1997 .

[12]  D. Reinhoudt,et al.  An attempt to predict the gelation ability of hydrogen-bond-based gelators utilizing a glycoside library , 2000 .

[13]  P. Dastidar,et al.  Hydrogen bonded supramolecular network in organic salts: crystal structures of acid–base salts of dicarboxylic acids and amines , 2002 .

[14]  K. Hanabusa,et al.  Prominent Gelation and Chiral Aggregation of Alkylamides Derived from trans‐1,2‐Diaminocyclohexane , 1996 .

[15]  P. Vemula,et al.  In Situ Synthesis of Gold Nanoparticles Using Molecular Gels and Liquid Crystals from Vitamin-C Amphiphiles , 2007 .

[16]  P. Dastidar,et al.  Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures. , 2004, Chemistry.

[17]  K. V. van Bommel,et al.  Organic templates for the generation of inorganic materials. , 2003, Angewandte Chemie.

[18]  P. Dastidar,et al.  Facile preparation and structure-property correlation of low molecular mass organic gelators derived from simple organic salts , 2005 .

[19]  Takashi Komori,et al.  Thermal and Light Control of the Sol-Gel Phase Transition in Cholesterol-Based Organic Gels. Novel Helical Aggregation Modes As Detected by Circular Dichroism and Electron Microscopic Observation , 1994 .

[20]  P. Dastidar,et al.  Noncovalent Syntheses of Supramolecular Organo Gelators , 2006 .

[21]  P. Dastidar,et al.  New Series of Organogelators Derived from a Combinatorial Library of Primary Ammonium Monocarboxylate Salts , 2006 .

[22]  Ben L Feringa,et al.  Reversible Optical Transcription of Supramolecular Chirality into Molecular Chirality , 2004, Science.

[23]  Richard G. Weiss,et al.  Liquid-crystalline solvents as mechanistic probes. 24. A novel gelator of organic liquids and the properties of its gels , 1987 .

[24]  R. E. Marsh,et al.  The crystal structure of trimesic acid (benzene-1,3,5-tricarboxylic acid) , 1969 .

[25]  A. Hamilton,et al.  Water gelation by small organic molecules. , 2004, Chemical reviews.

[26]  R. Vreeker,et al.  Rheology and thermotropic properties of bis-urea-based organogels in various primary alcohols , 2000 .

[27]  P. Dastidar,et al.  Cation-Induced Supramolecular Isomerism in the Hydrogen-Bonded Network of Secondary Ammonium Monocarboxylate Salts: A New Class of Organo Gelator and Their Structures , 2006 .

[28]  P. Dastidar,et al.  From nonfunctional lamellae to functional nanotubes. , 2006, Organic letters.

[29]  R. Weiss,et al.  Evidence for random parallel and anti-parallel packing between neighbouring cholesteryl 4-(2-anthryloxy)butyrate (CAB) molecules in the cholesteric liquid-crystalline phase. Identification of the four photodimers from CAB , 1989 .

[30]  B. Kachar,et al.  Liquid-crystalline solvents as mechanistic probes. Part 37. Novel family of gelators of organic fluids and the structure of their gels , 1989 .

[31]  K. Seddon,et al.  The hydrogen bond and crystal engineering , 1994 .

[32]  Richard G. Weiss,et al.  Gelation of Organic Liquids by Some 5α-Cholestan-3β-yl N-(2-Aryl)carbamates and 3β-Cholesteryl 4-(2-Anthrylamino)butanoates. How Important Are H-Bonding Interactions in the Gel and Neat Assemblies of Aza Aromatic-Linker-Steroid Gelators?† , 2000 .

[33]  M. Hollingsworth Crystal Engineering: from Structure to Function , 2002, Science.

[34]  Subi J. George,et al.  Molecular wire encapsulated into pi organogels: efficient supramolecular light-harvesting antennae with color-tunable emission. , 2007, Angewandte Chemie.

[35]  P. Dastidar,et al.  An Easy To Prepare Organic Salt as a Low Molecular Mass Organic Gelator Capable of Selective Gelation of Oil from Oil/Water Mixtures , 2003 .

[36]  P. Dastidar,et al.  Supramolecular assemblies in salts and co-crystals of imidazoles with dicarboxylic acids , 2003 .

[37]  B. Feringa,et al.  Geminal bis-ureas as gelators for organic solvents: gelation properties and structural studies in solution and in the gel state , 2000, Chemistry.

[38]  Gautam R. Desiraju,et al.  Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis , 1995 .

[39]  Gautam R Desiraju,et al.  Crystal engineering: a holistic view. , 2007, Angewandte Chemie.

[40]  R. Weiss,et al.  Structural Study of Cholesteryl Anthraquinone-2-carboxylate (CAQ) Physical Organogels by Neutron and X-ray Small Angle Scattering , 1996 .

[41]  Jean-Marie Lehn,et al.  Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture) , 1988 .

[42]  Bing Xu,et al.  Using a kinase/phosphatase switch to regulate a supramolecular hydrogel and forming the supramolecular hydrogel in vivo. , 2006, Journal of the American Chemical Society.

[43]  A. Wynne,et al.  An effective, cosmetically acceptable, novel hydro-gel emollient for the management of dry skin conditions , 2002, The Journal of dermatological treatment.

[44]  Takashi Kato Self-Assembly of Phase-Segregated Liquid Crystal Structures , 2002, Science.

[45]  Apurba K. Das,et al.  Smart oligopeptide gels: in situ formation and stabilization of gold and silver nanoparticles within supramolecular organogel networks. , 2006, Chemical communications.

[46]  Masayoshi Aoki,et al.  New cholesterol-based gelators with light- and metal-responsive functions , 1991 .

[47]  P. Dastidar Crystal structure of the inclusion complex of cholic acid with 4-aminopyridine: a novel supramolecular architecture of cholic acid , 2000 .

[48]  A. Heeres,et al.  Responsive cyclohexane-based low-molecular-weight hydrogelators with modular architecture. , 2004, Angewandte Chemie.

[49]  Asish Pal,et al.  Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles. , 2008, Chemistry.

[50]  R. Weiss,et al.  Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids. , 2006, Accounts of chemical research.

[51]  S. Okabe,et al.  Facile Syntheses of a Class of Supramolecular Gelator Following a Combinatorial Library Approach: Dynamic Light Scattering and Small-Angle Neutron Scattering Studies , 2005 .

[52]  B. Feringa,et al.  New Functional Materials Based on Self‐Assembling Organogels: From Serendipity towards Design , 2000 .

[53]  K. Hanabusa,et al.  In situ organogelation at room temperature: direct synthesis of gelators in organic solvents. , 2004, Organic & biomolecular chemistry.

[54]  Neralagatta M Sangeetha,et al.  Supramolecular gels: functions and uses. , 2005, Chemical Society reviews.

[55]  P. Dastidar,et al.  Ascertaining the 1D Hydrogen-Bonded Network in Organic Ionic Solids , 2005 .

[56]  R. Weiss,et al.  Organogels and Low Molecular Mass Organic Gelators , 2000 .

[57]  M. C. Feiters,et al.  A tailored organometallic gelator with enhanced amphiphilic character and structural diversity of gelation. , 2007, Chemical communications.

[58]  P. Dastidar,et al.  An easy access to an organometallic low molecular weight gelator: a crystal engineering approach , 2008 .

[59]  P. Dastidar,et al.  Instant gelation of various organic fluids including petrol at room temperature by a new class of supramolecular gelators , 2006 .

[60]  D. Smith,et al.  Dendritic Gels—Many Arms Make Light Work , 2006 .

[61]  Otto Ermer,et al.  Five-fold diamond structure of adamantane-1,3,5,7-tetracarboxylic acid , 1988 .

[62]  G. Koper,et al.  Headgroup mobility in lecithin inverse worm-like micelles , 1997 .

[63]  E. Ostuni,et al.  Novel X‐ray Method for In Situ Determination of Gelator Strand Structure: Polymorphism of Cholesteryl Anthraquinone‐2‐carboxylate , 1996 .

[64]  A. Govindaraj,et al.  Hydrogel route to nanotubes of metal oxides and sulfates , 2003 .

[65]  T. Naota,et al.  Molecules that assemble by sound: an application to the instant gelation of stable organic fluids. , 2005, Journal of the American Chemical Society.

[66]  D. Mooney,et al.  Hydrogels for tissue engineering. , 2001, Chemical Reviews.

[67]  Giuseppe Bruno,et al.  A refinement of the benzoic acid structure at room temperature , 1980 .

[68]  O. Gronwald,et al.  Gelators for organic liquids based on self-assembly: A new facet of supramolecular and combinatorial chemistry , 2002 .

[69]  Richard G. Weiss,et al.  Physical Gelation of Organic Fluids by Anthraquinone−Steroid-Based Molecules. Structural Features Influencing the Properties of Gels , 1996 .

[70]  K. Biradha,et al.  Supramolecular Synthesis of Organic Laminates with Affinity for Aromatic Guests: A New Class of Clay Mimics , 1998 .

[71]  T. Kunitake,et al.  Synthetic Bilayer Membranes: Molecular Design, Self‐Organization, and Application , 1992 .

[72]  Richard G. Weiss,et al.  Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels. , 1997, Chemical reviews.

[73]  S. Bhattacharya,et al.  First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills , 2001 .