Using EPR spectroscopy as a unique probe of molecular-scale reorganization and solvation in self-Assembled gel-phase materials

Langmuir

Volumn 30, Issue 30, 2014, Pages 9210-9218

  Caragheorgheopol, Agneta ^a   Edwards, William ^b   Hardy, John G ^b   Smith, David K ^b   Chechik, Victor ^b  

^a INSTITUTE OF PHYSICAL CHEMISTRY   (Romania)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY; GELATION; METABOLISM; MOLECULES; SELF ASSEMBLY; SOLS; SOLVATION; SPINNING (FIBERS); UREA;

ASSOCIATION CONSTANT; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; EXPLICIT SOLVENTS; GEL-PHASE MATERIALS; GEL-SOL TRANSITIONS; HIERARCHICAL SELF-ASSEMBLY; SELF ASSEMBLY PROCESS; SUPRAMOLECULAR GELS;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

EID: 84905695277     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la501641q     Document Type: Article

References (60)

1. Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Terech, P., Weiss, R. G., Eds.; Springer: Dordrecht, Netherlands, 2006.
2. Steed, J. W. Supramolecular Gel Chemistry: Developments over the Last Decade Chem. Commun. 2011, 47, 1379-1383
3. Banerjee, S.; Das, R. K.; Maitra, U. Supramolecular Gels 'in Action' J. Mater. Chem. 2009, 19, 6649-6687
4. Hirst, A. R.; Escuder, B.; Miravet, J. F.; Smith, D. K. High-Tech Applications of Self-Assembling Supramolecular Nanostructured Gel-Phase Materials: From Regenerative Medicine to Electronic Devices Angew. Chem., Int. Ed. 2008, 47, 8002-8018
5. Skilling, K. J.; Citossi, F.; Bradshaw, T. D.; Ashford, M.; Kellam, B.; Marlow, M. Insights Into Low Molecular Mass Organic Gelators: a Focus on Drug Delivery and Tissue Engineering Applications Soft Matter 2014, 10, 237-256
6. van Esch, J. H. We Can Design Molecular Gelators, But Do We Understand Them? Langmuir 2009, 25, 8392-8394
7. Raeburn, J.; Cardoso, A. Z.; Adams, D. J. The Importance of the Self-Assembly Process to Control Mechanical Properties of Low Molecular Weight Hydrogels Chem. Soc. Rev. 2013, 42, 5143-5156
8. Nebot, V. J.; Smith, D. K. Techniques for the Characterisation of Molecular Gels. In Functional Molecular Gels; Escuder, B.; Miravet, J. F., Eds.; RSC Publishing: Cambridge, UK, 2014; pp 30-66.
9. Yu, G.; Yan, X.; Han, C.; Huang, F. Characterization of Supramolecular Gels Chem. Soc. Rev. 2013, 42, 6697-6722
10. Hirst, A. R.; Coates, I. A.; Boucheteau, T. R.; Miravet, J. F.; Escuder, B.; Castelletto, V.; Hamley, I. W.; Smith, D. K. 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
11. Edwards, W.; Smith, D. K. Dynamic Evolving Two-Component Supramolecular Gels - Hierarchical Control over Component Selection in Complex Mixtures J. Am. Chem. Soc. 2013, 135, 5911-5920
12. Bouguet-Bonnet, S.; Yemloul, M.; Canet, D. New Application of Proton Nuclear Spin Relaxation Unraveling the Intermolecular Structural Features of Low-Molecular-Weight Organogel Fibers J. Am. Chem. Soc. 2012, 134, 10621-10627
13. Smirnov, A. EPR studies of nanomaterials. In Multifrequency Electron Paramagnetic Resonance: Theory and Applications; Misra, S. K., Ed.; Wiley-VCH: Weinheim, Germany, 2011; pp 825-843.
14. Klare, J. Site-Directed Spin Labeling and Electron Paramagnetic Resonance (EPR) Spectroscopy: A Versatile Tool to Study Protein-Protein Interactions. In Protein Interactions; Cai, J.; Wang, R. E., Eds.; InTech: Winchester, 2012; Vol. 21, DOI: 10.5772/37209.
15. Chechik, V.; Caragheorgheopol, A. Getting an Inside View of Nanomaterials with Spin Labels and Spin Probes. In Electron Paramagnetic Resonance; Gilbert, B. C.; Davies, M. J.; Murphy, D. M., Eds.; RSC Publishing: Cambridge, UK, 2007; Vol. 20, pp 96-130.
16. Caragheorgheopol, A.; Caldararu, H. EPR Spin-Labelling and Spin-Probe Studies of Self-Assembled Systems. In Electron Paramagnetic Resonance; Gilbert, B. C.; Davies, M. J.; McLauchlan, K. A., Eds.; RSC Publishing: Cambridge, UK, 2000; Vol. 17, pp 205-245.
17. Lucarini, M.; Mezzina, E. EPR Investigations of Organic Non-Covalent Assemblies with Spin Labels and Spin Probes. In Electron Paramagnetic Resonance; Gilbert, B. C.; Murphy, D. M.; Chechik, V., Eds.; RSC Publishing: Cambridge, UK, 2011; Vol. 22, pp 41-70.
18. Nakabayashi, K.; Kawano, M.; Yoshizawa, M.; Ohkoshi, S.-i.; Fujita, M. Cavity-Induced Spin-Spin Interaction between Organic Radicals within a Self-Assembled Coordination Cage J. Am. Chem. Soc. 2004, 126, 16694-16695
19. Hinderberger, D. EPR Spectroscopy in Polymer Science Top. Curr. Chem. 2012, 321, 67-89
20. Ruthstein, S.; Goldfarb, D. An EPR Tool Box for Exploring the Formation and Properties of Ordered Template Mesoporous Materials. In Electron Paramagnetic Resonance; Gilbert, B. C.; Davies, M. J.; Murphy, D. M., Eds.; RSC Publishing: Cambridge, UK, 2008; Vol. 21, pp 184-215.
21. Lucarini, M.; Pasquato, L. ESR Spectroscopy as a Tool to Investigate the Properties of Self-Assembled Monolayers Protecting Gold Nanoparticles Nanoscale 2010, 2, 668-76
22. Kveder, M.; Andreis, M.; Makarevic, J.; Jokic, M.; Rakvin, B. EPR Study of Low Molecular Weight Organogels by Means of a Nitroxide Spin Probe Chem. Phys. Lett. 2006, 420, 443-447
23. Andreis, M.; Caric, D.; Vujicic, N. S.; Jokic, M.; Zinic, M.; Kveder, M. Self-Assembly of Gelator Molecules in Liquid Crystals Studied by ESR Chem. Phys. 2012, 403, 81-88
24. Puigmarti-Luis, J.; del Pino, A. P.; Laukhin, V.; Feldborg, L. N.; Rovira, C.; Laukhina, E.; Amabilino, D. B. Solvent Effect on the Morphology and Function of Novel Gel-Derived Molecular Materials J. Mater. Chem. 2010, 20, 466-474
25. Mannini, M.; Cicchi, S.; Berti, D.; Caneschi, A.; Brandi, A.; Lascialfari, L.; Sorace, L. Radical-Functionalised Gel: A Building-Block Strategy for Magnetochiral Assembly ChemPlusChem 2013, 78, 149-156
26. Wu, Y.; Hirai, Y.; Tsunobuchi, Y.; Tokoro, H.; Eimura, H.; Yoshio, M.; Ohkoshi, S.; Kato, T. Supramolecular Approach to the Formation of Magneto-Active Physical Gels Chem. Sci. 2012, 3, 3007-3010
27. Yamanaka, M. Urea Derivatives as Low-Molecular-Weight Gelators J. Inclusion Phenom. Macrocyclic Chem. 2013, 77, 33-48
28. Steed, J. W. Anion-Tuned Supramolecular Gels: a Natural Evolution from Urea Supramolecular Chemistry Chem. Soc. Rev. 2010, 39, 3686-3699
29. Hardy, J. G.; Hirst, A. R.; Ashworth, I. A.; Brennan, C.; Smith, D. K. Exploring Molecular Recognition Pathways within a Family of Gelators with Different Hydrogen Bonding Motifs Tetrahedron 2007, 63, 7397-7406
30. Coates, I. A.; Smith, D. K. Controlled Self-Assembly-Synthetic Tunability and Covalent Capture of Nanoscale Gel Morphologies Chem. - Eur. J. 2009, 15, 6340-6344
31. Saracino, G. A. A.; Tedeschi, A.; D'Errico, G.; Improta, R.; Franco, L.; Ruzzi, M.; Corvaia, C.; Barone, V. Solvent Polarity and pH Effects on the Magnetic Properties of Ionizable Nitroxide Radicals: A Combined Computational and Experimental Study of 2,2,5,5-Tetramethyl-3-carboxypyrrolidine and 2,2,6,6-Tetramethyl-4-carboxypiperidine Nitroxides J. Phys. Chem. A 2002, 106, 10700-10706
32. Budil, D. E.; Lee, S.; Saxena, S.; Freed, J. H. Nonlinear-Least-Squares Analysis of Slow-Motion EPR Spectra in One and Two Dimensions Using a Modified Levenberg-Marquardt Algorithm J. Magn. Reson., Ser. A 1996, 120, 155-189
33. 3phen Complex J. Colloid Interface Sci. 2013, 398, 95-102
34. Roy, B.; Saha, A.; Esterrani, A.; Nandi, A. K. Time Sensitive, Temperature and pH Responsive Photoluminescence Behaviour of a Melamine Containing Bicomponent Hydrogel Soft Matter 2010, 6, 3337-3345
35. Huang, X.; Terech, P.; Raghavan, S. R.; Weiss, R. G. Kinetics of 5α-Cholestan-3β-yl N-(2-Naphthyl)carbamate/n-Alkane Organogel Formation and Its Influence on the Fibrillar Networks J. Am. Chem. Soc. 2005, 127, 4336-4344
36. Huang, X.; Raghavan, S. R.; Terech, P.; Weiss, R. G. Distinct Kinetic Pathways Generate Organogel Networks with Contrasting Fractality and Thixotropic Properties J. Am. Chem. Soc. 2006, 128, 15341-15352
37. Goldstein, R. F.; Stryer, L. Cooperative polymerization reactions. Analytical approximations, numerical examples, and experimental strategy Biophys. J. 1986, 50, 583-599
38. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Supramolecular Polymerization Chem. Rev. 2009, 109, 5687-5754
39. Hunter, C. A.; Anderson, H. L. What is Cooperativity? Angew. Chem., Int. Ed. 2008, 48, 7488-7499
40. Grampp, G.; Landgraf, S.; Grigor'ev, I. A.; Shapiro, A. B.; Kokorin, A. I. Intramolecular Spin Exchange in Flexible Short-Chain Biradicals in Solutions with Various Viscosity Appl. Magn. Reson. 2000, 26, 245-252
41. Townshend, A.; Jackwerth, E. Precipitation of Major Constituents for Trace Preconcentration: Potential and Problems Pure Appl. Chem. 1989, 61, 1643-1656
42. Munakata, M.; Toyomasu, S. Quantitative Treatment of the Distribution Coefficient for Coprecipitation of Metal Oxalates Anal. Chem. 1972, 44, 2057-2060
43. 3-Symmetric Organogelators: Cooperativity, Solvent, and Gelation Relationship Chem. - Eur. J. 2013, 19, 3239-3248
44. Smith, D. K. Molecular Gels-Underpinning Nanoscale Materials with Organic Chemistry Tetrahedron 2007, 63, 7283-7284
45. Niu, L.; Song, J.; Li, J.; Tao, N.; Lu, M.; Fan, K. Solvent Effects on the Gelation Performance of Melamine and 2-Ethylhexylphosphoric Acid Mono-2-ethylhexyl Ester in Water-Organic Mixtures Soft Matter 2013, 9, 7780-7786
46. Bielejewski, M.; Lapinski, A.; Luboradzki, R.; Tritt-Goc, J. Solvent Effect on 1,2-O-(1-Ethylpropylidene)-α-d-glucofuranose Organogel Properties Langmuir 2009, 25, 8274-8279
47. Rogers, M. A.; Marangoni, A. G. Solvent-Modulated Nucleation and Crystallization Kinetics of 12-Hydroxystearic Acid: A Nonisothermal Approach Langmuir 2009, 25, 8556-8566
48. Raynal, M.; Bouteiller, L. Organogel Formation Rationalized by Hansen Solubility Parameters Chem. Commun. 2011, 8271-8273
49. Muro-Small, M. L.; Chen, J.; McNeil, A. J. Dissolution Parameters Reveal Role of Structure and Solvent in Molecular Gelation Langmuir 2011, 27, 13248-13253
50. Wu, S.; Gao, J.; Emge, T. J.; Rogers, M. A. Influence of Solvent on the Supramolecular Architectures in Molecular Gels Soft Matter 2013, 9, 5942-5950
51. Fan, K.; Niu, L.; Li, J.; Feng, R.; Qu, R.; Liu, T.; Song, J. Application of Solubility Theory in Bi-component Hydrogels of Melamine with Di(2-ethylhexyl)phosphoric Acid Soft Matter 2013, 9, 3057-3062
52. Jonkheijm, P.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Probing the Solvent-Assisted Nucleation Pathway in Chemical Self-Assembly Science 2006, 313, 80-83
53. Cantekin, S.; Nakano, Y.; Everts, J. C.; van der Schoot, P.; Meijer, E. W.; Palmans, A. R. A. A Stereoselectively Deuterated Supramolecular Motif to Probe the Role of Solvent During Self-Assembly Processes Chem. Commun. 2012, 48, 3803-3805
54. Pinault, T.; Isare, B.; Boutellier, L. Solvents with Similar Bulk Properties Induce Distinct Supramolecular Architectures ChemPhysChem 2006, 7, 816-819
55. Mukai, M.; Minamikawa, H.; Aoyagi, M.; Asakawa, M.; Shimizu, T.; Kogiso, M. Solvent-Chirality Selective Organogelation by Chiral Aspartame Lipids Soft Matter 2012, 8, 11979-11981
56. Yemloul, M.; Steiner, E.; Robert, A.; Bouguet-Bonnet, S.; Allix, F.; Jamart-Gregoire, B.; Canet, D. Solvent Dynamical Behavior in an Organogel Phase As Studied by NMR Relaxation and Diffusion Experiments J. Phys. Chem. B 2011, 115, 2511-2517
57. Tritt-Goc, J.; Bielejewski, M.; Luboradzki, R. Interaction of Chlorobenzene with Gelator in Methyl-4,6-O-(p-nitrobenzylidene)-α-d- glucopyranoside Gel Probed by Proton Fast Field Cycling NMR Relaxometry Tetrahedron 2011, 67, 8170-8176
58. Bielejewski, M.; Kowalczuk, J.; Kaszynska, J.; Lapinski, A.; Luboradzki, R.; Demchuk, O.; Tritt-Goc, J. Novel Supramolecular Organogels Based on a Hydrazide Derivative: Non-Polar Solvent-Assisted Self-Assembly, Selective Gelation Properties, Nanostructure, Solvent Dynamics Soft Matter 2013, 9, 7501-7514
59. Riplinger, C.; Kao, J. P. Y.; Rosen, G. M.; Kathirvelu, V.; Eaton, G. R.; Eaton, S. S.; Kutateladze, A.; Neese, F. Interaction of Radical Pairs Through-Bond and Through-Space: Scope and Limitations of the Point-Dipole Approximation in Electron Paramagnetic Resonance Spectroscopy J. Am. Chem. Soc. 2009, 131, 10092-10106
60. Steinhoff, H. J.; Radzwill, N.; Thevis, W.; Lenz, V.; Brandenburg, D.; Antson, A.; Dodson, G.; Wollmer, A. Determination of Interspin Distances Between Spin Labels Attached to Insulin: Comparison of Electron Paramagnetic Resonance Data with the X-Ray Structure Biophys. J. 1997, 73, 3287-3298