Studies on organogelation of self assembling bis urea type low molecular weight molecules
Source abstract
Abstract
A novel class of toluene based bis urea compounds carrying linear fatty acid units and semicarbazide linkages has been synthesised. The compounds were exhibiting thermoreversible gelation at concentrations below 10 mg/mL in common organic solvents, both aliphatic and aromatic. The effect of the chain length variation of fatty acid units on gelation properties like gelation concentration, gelation time and gel melting temperatures were studied. Choosing a particular gelator of fixed chain length and a specific solvent, the effect of the concentration on the gelation properties were studied. The thermal studies using DSC revealed the presence of phase transitions corresponding to the premelting and melting of the gels during the heating cycle. The morphology of the xerogels studied using SEM revealed a three dimensional network structure while the WAXS studies showed no crystallinity in the xerogels. IR spectra of the gels (solvent subtracted) and solutions in the corresponding solvent showed that a high degree of inter-molecular H bonding exists and absorptions corresponding to NH stretching shifted to lower wave numbers. Thus simple bisurea type of compounds exhibiting gelation ability in a wide range of solvents can be used for making functional gels for various applications.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Supramolecular Self-Assembly in Materials · Polydiacetylene-based materials and applications · Photochromic and Fluorescence Chemistry
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (32)
Show source-provided references
1. van Esch J, Kellogg RM, Feringa BL (1997) Di-urea compounds as gelators for organic solvents. Tetrahedron Lett 38:281–28410.1016/S0040-4039(96)02292-7 ↗
2. de Loos M, van Esch J, Stokroos I, Kellogg RM, Feringa RL (1997) Remarkable stabilization of self-assembled organogels by polymerization. J Am Chem Soc 119:12675–1267610.1021/ja972899z ↗
3. van Esch J, Schoonbeek F, de Loos M, Kooijman H, Spek AL, Kellogg RM, Feringa BL (1999) Cyclic bis-urea compounds as gelators for organic solvents. Chem Eur J 5:937–95010.1002/(SICI)1521-3765(19990301)5:3<937::AID-CHEM937>3.0.CO;2-0 ↗
4. Schoonbeek FS, van Esch JH, Hulst R, Kellogg RM, Feringa BL (2000) Geminal bis-ureas as gelators for organic solvents: gelation properties and structural studies in solution and in the gel state. Chem Eur J 6:2633–264310.1002/1521-3765(20000717)6:14<2633::AID-CHEM2633>3.0.CO;2-L ↗
5. Brinksma J, Feringa BL, Kellogg RM, Vreeker R, van Esch J (2000) Rheology and thermotropic properties of bis-urea-based organogels in various primary alcohols. Langmuir 16:9249–925510.1021/la000839s ↗
6. de Loos M, van Esch J, Kellogg RM, Feringa BL (2001) Chiral recognition in bis-urea-based aggregates and organogels through cooperative interactions. Angew Chem Int Ed 40:613–61610.1002/1521-3773(20010202)40:3<613::AID-ANIE613>3.0.CO;2-K ↗
7. van der Laan S, Feringa BL, Kellogg RM, van Esch J (2002) Remarkable polymorphism in gels of new azobenzene bis-urea gelators. Langmuir 18:7136–714010.1021/la025561d ↗
8. De Loos M, Friggeri M, Van Esch J, Kellogg RM, Feringa BL (2005) Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions. Org Biomol Chem 3:1631–163910.1039/b500837a ↗
9. Carr J, Melendez R, Geib SJ, Hamilton AD (1998) The design of organic gelators: solution and solid state properties of a family of bis-ureas. Tetrahedron Lett 39:7447–745010.1016/S0040-4039(98)01667-0 ↗
10. Shi C, Huang Z, Kilic S, Xu J, Enick RM, Beckman EJ, Carr AJ, Melendez RE, Hamilton AD (1999) The gelation of CO2: a sustainable route to the creation of microcellular materials. Science 286:1540–154310.1126/science.286.5444.1540 ↗
11. Estroff LA, Hamilton AD (2000) Effective gelation of water using a series of bis-urea dicarboxylic acids. Angew Chem Int Ed 39:3447–345010.1002/1521-3773(20001002)39:19<3447::AID-ANIE3447>3.0.CO;2-X ↗
12. Wang G, Hamilton AD (2002) Synthesis and self-assembling properties of polymerizable organogelators. Chem Eur J 8:1954–196110.1002/1521-3765(20020415)8:8<1954::AID-CHEM1954>3.0.CO;2-X ↗
13. Hanabusa K, Shimura K, Hirose K, Kimura M, Shirai H (1996) Formation of organogels by intermolecular hydrogen bonding between ureylene segment. Chem Lett 10:885–88610.1246/cl.1996.885 ↗
14. Kato T, Kutsuna T, Hanabusa K, Ukon M (1998) Gelation of room-temperature liquid crystals by the association of a trans-1,2-bis(amino)cyclohexane derivative. Adv Mater 10:606–60810.1002/(SICI)1521-4095(199805)10:8<606::AID-ADMA606>3.0.CO;2-T ↗
15. Hanabusa K, Maesaka Y, Kimura M, Shirai H (1999) New gelators based on 2-amino-2-phenylethanol: close gelator-chiral structure relationship. Tetrahedron Lett 40:2385–238810.1016/S0040-4039(99)00195-1 ↗
16. Mizoshita N, Hanabusa K, Kato T (1999) Self-aggregation of an amino acid derivative in a liquid-crystalline physical gel—faster response to electric fields. Adv Mater 11:392–39410.1002/(SICI)1521-4095(199903)11:5<392::AID-ADMA392>3.0.CO;2-Q ↗
17. Yabuuchi K, Marfo-Owusu E, Kato T (2003) A new urea gelator: incorporation of intra- and intermolecular hydrogen bonding for stable 1D self-assembly. Org Biomol Chem 1:3464–346910.1039/b307149a ↗
18. Suzuki M, Nakajima Y, Yumoto M, Kimura M, Shirai H, Hanabusa K (2004) In situ organogelation at room temperature: direct synthesis of gelators in organic solvents. Org Biomol Chem 2:1155–115910.1039/b401683a ↗
19. Jeong Y, Hanabusa K, Masunaga H, Akiba I, Miyoshi K, Sakurai S, Sakurai K (2005) Solvent/gelator interactions and supramolecular structure of gel fibers in cyclic bis-urea/primary alcohol organogels. Langmuir 21:586–59410.1021/la047538t ↗
20. Beginn U, Tartsch B (2001) Bis[(alkoxy)benzoylsemicarbazides]—a new class of powerful organogelators. Chem Commun 19:192410.1039/b106133j ↗
21. Rodrguez-Llansola F, Hermida-Merino D, Nieto-Ortega B, Ramrez FJ, Lopez Navarrete JT, Casado J, Hamley IW, Escuder B, Hayes W, Miravet JF (2012) Self-assembly studies of a chiral bisurea-based superhydrogelator. Chem Eur J 18:14725–1473110.1002/chem.201200707 ↗
22. Lortie F, Boileau S, Bouteiller L, Chassenieux C, Deme´ B, Ducouret G, Jalabert M, Laupreˆtre F, Terech P (2002) Structural and rheological study of a bis-urea based reversible polymer in an apolar solvent. Langmuir 18:7218–722210.1021/la0255166 ↗
23. Zweep N, Hopkinson A, Meetsma A, Browne WR, Feringa BL, van Esch JH (2009) Balancing hydrogen bonding and van der Waals interactions in cyclohexane-based bisamide and bisurea organogelators†. Langmuir 25(15):8802–880910.1021/la9004714 ↗
24. Moniruzzaman M, Goodbrand B, Sundararajan PR (2003) Morphology and thermal behavior of self-assembling carbamates. J Phys Chem B 107:8416–842310.1021/jp035336k ↗
25. Moniruzzaman M, Sundararajan PR (2005) Role of hydrogen bonds in controlling the morphology of self-assembling carbamate systems. J Phys Chem B 109:1192–119710.1021/jp045592c ↗
26. Khanna S, Moniruzzaman M, Sundararajan PR (2006) Influence of single versus double hydrogen-bonding motif on the crystallization and morphology of self-assembling carbamates with alkyl side chains: model system for polyurethanes. J Phys Chem B 110:15251–1526010.1021/jp0619843 ↗
27. Moniruzzaman M, Sundararajan PR (2005) Low molecular weight organogels based on long-chain carbamates. Langmuir 21:3802–380710.1021/la047449g ↗
28. Ohsedo Y, Miyamoto M, Watanabe H, Oono M, Tanaka A (2013) Alkylhydrazide derivatives as new organogelators and their potential ability to gel electrolytes. Bull Chem Soc Jpn 86(5):671–67310.1246/bcsj.20120352 ↗
29. Campbell TW, Foldi VS, Farago J (1959) Condensation polymers from diisocyanates with dihydrazides and hydrazine. J Appl Polym Sci 2:155–16210.1002/app.1959.070020504 ↗
30. Vogel AI, Tatchell AR, Furnis BS, Hannaford AJ, Smith PWG (1996) Vogel’s text book of practical organic chemistry, 5th ed. ELBS, London, p 703
31. van Esch J, de Feyter S, Kellogg RM, de Schryver FB, Feringa L (1997) Self-assembly of bisurea compounds in organic solvents and on solid substrates. Chem Eur J 3:1238–124310.1002/chem.19970030811 ↗
32. Hirst AR, Smith DK, Harrington JP (2005) Unique nanoscale morphologies underpinning organic gel-phase materials. Chem Eur J 11:6552–655910.1002/chem.200500501 ↗