Investigation of the Adsorption Processes of Fluorocarbon and Hydrocarbon Anions at the Solid-Solution Interface of Macromolecular Imprinted Polymer Materials

Journal of Physical Chemistry C

Volumn 120, Issue 12, 2016, Pages 6553-6568

  Karoyo, Abdalla H ^a   Wilson, Lee D ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; ADSORPTION ISOTHERMS; AGGLOMERATION; CALORIMETERS; CALORIMETRY; CARBOXYLATION; CROSSLINKING; DIFFERENTIAL SCANNING CALORIMETRY; FATTY ACIDS; HYDROCARBONS; HYDROPHOBICITY; INTERFACES (MATERIALS); IONS; ISOTHERMS; MACROMOLECULES; MONOLAYERS; MULTILAYERS; NEGATIVE IONS; POLYMERS; SELF ASSEMBLED MONOLAYERS;

HYDROCARBON SURFACTANTS; INTERFACIAL ADSORPTION; INTERFACIAL INTERACTION; ISOTHERMAL TITRATION CALORIMETRY; PERFLUOROOCTANE SULFONATES; PERFLUOROOCTANOIC ACID; SELF ASSEMBLED MULTILAYERS; SOLID-SOLUTION INTERFACE;

SOLID SOLUTIONS;

EID: 84963558379     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/acs.jpcc.5b12246     Document Type: Article

References (101)

1. Crini, G.; Bertini, S.; Torri, G.; Naggi, A.; Sforzini, D.; Vecchi, C.; Janus, L.; Lekchiri, Y.; Morcellet, M. Sorption of Aromatic Compounds in Water Using Insoluble J. Appl. Polym. Sci. 1997, 68, 1973-1978 10.1002/(SICI)1097-4628(19980620)68:12<1973::AID-APP11>3.3.CO;2-R
2. Crini, G. Studies on Adsorption of Dyes on Beta-Cyclodextrin Polymer Bioresour. Technol. 2003, 90, 193-198 10.1016/S0960-8524(03)00111-1
3. Crini, G.; Peindy, H. N.; Gimbert, F.; Robert, C. Removal of C.I. Basic Green 4 (Malachite Green) from Aqueous Solutions by Adsorption Using Cyclodextrin-Based Adsorbent: Kinetic and Equilibrium Studies Sep. Purif. Technol. 2007, 53, 97-110 10.1016/j.seppur.2006.06.018
4. Deng, S.; Niu, L.; Bei, Y.; Wang, B.; Huang, J.; Yu, G. Adsorption of Perfluorinated Compounds on Aminated Rice Husk Prepared by Atom Transfer Radical Polymerization Chemosphere 2013, 91, 124-130 10.1016/j.chemosphere.2012.11.015
5. Deng, S.; Shuai, D.; Yu, Q.; Huang, J.; Yu, G. Selective Sorption of Perfluorooctane Sulfonate on Molecularly Imprinted Polymer Adsorbents Front. Environ. Sci. Eng. China 2009, 3, 171-177 10.1007/s11783-009-0017-4
6. Deng, S.; Yu, Q.; Huang, J.; Yu, G. Removal of Perfluorooctane Sulfonate from Wastewater by Anion Exchange Resins: Effects of Resin Properties and Solution Chemistry Water Res. 2010, 44, 5188-5195 10.1016/j.watres.2010.06.038
7. Mamba, B. B.; Krause, R. W.; Malefetse, T. J.; Nxumalo, E. N. Monofunctionalized Cyclodextrin Polymers for the Removal of Organic Pollutants from Water Environ. Chem. Lett. 2007, 5, 79-84 10.1007/s10311-006-0082-x
8. Mamba, G.; Mbianda, X. Y.; Govender, P. P. Phosphorylated Multiwalled Carbon Nanotube-Cyclodextrin Polymer: Synthesis, Characterisation and Potential Application in Water Purification Carbohydr. Polym. 2013, 98, 470-476 10.1016/j.carbpol.2013.06.034
9. Mohamed, M. H.; Wilson, L. D.; Headley, J. V.; Peru, K. M. Sequestration of Naphthenic Acids from Aqueous Solution Using β-Cyclodextrin-Based Polyurethanes Phys. Chem. Chem. Phys. 2011, 13, 1112-1122 10.1039/C0CP00421A
10. Pratt, D. Y.; Wilson, L. D.; Kozinski, J. A.; Mohart, A. M. Preparation and Sorption Studies of β-Cyclodextrin/ Epichlorohydrin Copolymers J. Appl. Polym. Sci. 2010, 116, 2982-2989 10.1002/app.31824
11. Wilson, L. D.; Guo, R. Preparation and Sorption Studies of Polyester Microsphere Copolymers Containing β-Cyclodextrin J. Colloid Interface Sci. 2012, 387, 250-261 10.1016/j.jcis.2012.07.092
12. Yu, Q.; Deng, S.; Yu, G. Selective Removal of Perfluorooctane Sulfonate from Aqueous Solution Using Chitosan-Based Molecularly Imprinted Polymer Adsorbents Water Res. 2008, 42, 3089-3097 10.1016/j.watres.2008.02.024
13. Bhattarai, B.; Muruganandham, M.; Suri, R. P. S. Development of High Efficiency Silica Coated β-Cyclodextrin Polymeric Adsorbent for the Removal of Emerging Contaminants of Concern from Water J. Hazard. Mater. 2014, 273, 146-154 10.1016/j.jhazmat.2014.03.044
14. Kawano, S.; Kida, T.; Takemine, S.; Matsumura, C.; Nakano, T.; Kuramitsu, M.; Adachi, K.; Akashi, M. Efficient Removal and Recovery of Perfluorinated Compounds from Water by Surface-Tethered β-Cyclodextrins on Polystyrene Particles Chem. Lett. 2013, 42, 392-394 10.1246/cl.121239
15. Karoyo, A. H.; Wilson, L. D. Tunable Macromolecular-Based Materials for the Adsorption of Perfluorooctanoic and Octanoic Acid Anions J. Colloid Interface Sci. 2013, 402, 196-203 10.1016/j.jcis.2013.03.065
16. Lee, C.-Y.; Pedram, E. O.; Hines, A. L. Adsorption of Oxalic, Malonic, and Succinic Acids on Activated Carbon J. Chem. Eng. Data 1986, 31, 133-136 10.1021/je00044a001
17. Somasundaran, P.; Krishnakumar, S. Adsorption of Surfactants and Polymers at the Solid-Liquid Interface Colloids Surf., A 1997, 123-124, 491-513 10.1016/S0927-7757(96)03829-0
18. Qaqish, S. E.; Urquhart, S. G.; Lanke, U.; Brunet, S. M. K.; Paige, M. F. Phase Separation of Palmitic Acid and Perfluorooctadecanoic Acid in Mixed Langmuir-Blodgett Monolayer Films Langmuir 2009, 25, 7401-7409 10.1021/la900308b
19. Asakawa, T.; Amada, K.; Miyagishi, S. Micellar Immiscibility of Lithium 1,1,2,2-Tetrahydroheptadecafluorodecyl Sulfate and Lithium Tetradecyl Sulfate Mixture Langmuir 1997, 13, 4569-4573 10.1021/la970131m
20. Holmberg, K.; Jonsson, B.; B. K.; B. L. Surfactants And Polymers In Aqueous Solutions, 2 nd ed.; John Wiley & Sons Ltd: Chechester, West Sussex, 2002; Vol. 14.
21. Wilson, L. D.; Siddall, S. R.; Verrall, R. E. A Spectral Displacement Study Of The Binding Constants Of Cyclodextrin-Hydrocarbon And Cyclodextrin-Fluorocarbon Surfactant Inclusion Complexes Can. J. Chem. 1997, 75, 927-933 10.1139/v97-111
22. Szejtli, J. Introduction and General Overview of Cyclodextrin Chemistry Chem. Rev. 1998, 98, 1743-1753 10.1021/cr970022c
23. Connors, K. a. The Stability of Cyclodextrin Complexes in Solution Chem. Rev. 1997, 97, 1325-1357 10.1021/cr960371r
24. Jobe, D. J.; Verrall, R. E.; Junquera, E.; Aicart, E. Effects of β-Cyclodextrin/Surfactant Complex Formation on the Surfactant Monomer-Micelle Exchange Rate in Aqueous Solutions of Sodium Perfluorooctanoate and β-Cyclodextrin J. Phys. Chem. 1994, 98, 10814-10818 10.1021/j100093a023
25. Junquera, E.; Tardajos, G.; Aicart, E. Effect of the Presence of Beta Cyclodextrin on the Micellization Process of Sodium Dodecyl or Sodium Perfluoroctanoate in Water Langmuir 1993, 9, 1213-1219 10.1021/la00029a011
26. Karoyo, A. H.; Borisov, A. S.; Wilson, L. D.; Hazendonk, P. Formation of Host-Guest Complexes of β-Cyclodextrin and Perfluorooctanoic Acid J. Phys. Chem. B 2011, 115, 9511-9527 10.1021/jp110806k
27. Palepu, R.; Reinsborough, V. C. Solution Inclusion Complexes of Cyclodextrins with Sodium Perfluorooctanoate Can. J. Chem. 1989, 67, 1550-1553 10.1139/v89-236
28. Palepu, R.; Reinsborough, V. C. Surfactant-cyclodextrin Interactions by Conductance Measurements Can. J. Chem. 1988, 66 (2) 325-328 10.1139/v88-056
29. Palepu, R.; Richardson, J. E.; Reinsborough, V. C. Binding Constants of & Cyclodextrin/Surfactant Inclusion by Conductivity Measurements Langmuir 1989, 5, 218-221 10.1021/la00085a041
30. Wilson, L. D.; Verrall, R. E. 19 F and 1 H NMR Investigation of Cyclodextrin/Fluorocarbon Alkyl Carboxylate Surfactant Inclusion Complexes Langmuir 1998, 14, 4710-4717 10.1021/la9802365
31. Wilson, L. D.; Verrall, R. E. Volumetric Study of Modified Cyclodextrin/hydrocarbon and /Fluorocarbon Surfactant Inclusion Complexes in Aqueous Solutions J. Phys. Chem. B 1998, 102, 480-488 10.1021/jp9725137
32. Wilson, L. D.; Verrall, R. E. H NMR Study of Cyclodextrin-Hydrocarbon Surfactant Inclusion Complexes in Aqueous Solutions Can. J. Chem. 1998, 76, 25-34 10.1139/v97-208
33. Xing, H.; Lin, S.-S.; Yan, P.; Xiao, J.-X.; Chen, Y.-M. NMR Studies on Selectivity of Beta-Cyclodextrin to Fluorinated/hydrogenated Surfactant Mixtures J. Phys. Chem. B 2007, 111, 8089-8095 10.1021/jp070198a
34. Tsianou, M.; Fajalia, A. I. Cyclodextrins and Surfactants in Aqueous Solution above the Critical Micelle Concentration: Where Are the Cyclodextrins Located? Langmuir 2014, 30, 13754-13764 10.1021/la5013999
35. Crini, G.; Morcellet, M. Synthesis and Applications of Adsorbents Containing Cyclodextrins J. Sep. Sci. 2002, 25, 789-813 10.1002/1615-9314(20020901)25:13<789::AID-JSSC789>3.0.CO;2-J
36. Du, Z.; Deng, S.; Bei, Y.; Huang, Q.; Wang, B.; Huang, J.; Yu, G. Adsorption Behavior and Mechanism of Perfluorinated Compounds on Various Adsorbents-A Review J. Hazard. Mater. 2014, 274, 443-454 10.1016/j.jhazmat.2014.04.038
37. Karoyo, A.; Wilson, L. Nano-Sized Cyclodextrin-Based Molecularly Imprinted Polymer Adsorbents for Perfluorinated Compounds - A Mini-Review Nanomaterials 2015, 5, 981-1003 10.3390/nano5020981
38. Wilson, L. D.; Mohamed, M. H.; Headley, J. V. Novel Materials For Environmental Remediation of Oil Sands Contaminants Rev. Environ. Health 2014, 29, 5-8 10.1515/reveh-2014-0005
39. Ulman, a. Formation and Structure of Self-Assembled Monolayers Chem. Rev. 1996, 96, 1533-1554 10.1021/cr9502357
40. Berg, M. C.; Zhai, L.; Cohen, R. E.; Rubner, M. F. Controlled Drug Release from Porous Polyelectrolyte Multilayers Biomacromolecules 2006, 7, 357-364 10.1021/bm050174e
41. Qu, Y.; Zhang, C.; Li, F.; Bo, X.; Liu, G.; Zhou, Q. Equilibrium and Kinetics Study on the Adsorption of Perfluorooctanoic Acid from Aqueous Solution onto Powdered Activated Carbon J. Hazard. Mater. 2009, 169, 146-152 10.1016/j.jhazmat.2009.03.063
42. Yu, Q.; Zhang, R.; Deng, S.; Huang, J.; Yu, G. Sorption of Perfluorooctane Sulfonate and Perfluorooctanoate on Activated Carbons and Resin: Kinetic and Isotherm Study Water Res. 2009, 43, 1150-1158 10.1016/j.watres.2008.12.001
43. Zhang, Q.; Deng, S.; Yu, G.; Huang, J. Removal of Perfluorooctane Sulfonate from Aqueous Solution by Crosslinked Chitosan Beads: Sorption Kinetics and Uptake Mechanism Bioresour. Technol. 2011, 102, 2265-2271 10.1016/j.biortech.2010.10.040
44. Yu, J.; Hu, J. Adsorption of Perfluorinated Compounds onto Activated Carbon and Activated Sludge J. Environ. Eng. 2011, 137, 945-951 10.1061/(ASCE)EE.1943-7870.0000402
45. Yao, Y.; Volchek, K.; Brown, C. E.; Robinson, A.; Obal, T. Comparative Study on Adsorption of Perfluorooctane Sulfonate (PFOS) and Perfluorooctanoate (PFOA) by Different Adsorbents in Water Water Sci. Technol. 2014, 70, 1983 10.2166/wst.2014.445
46. Zhang, R.; Somasundaran, P. Advances in Adsorption of Surfactants and Their Mixtures at Solid/solution Interfaces Adv. Colloid Interface Sci. 2006, 123-126, 213-229 10.1016/j.cis.2006.07.004
47. Tiberg, F.; Brinck, J.; Grant, L. Adsorption and Surface-Induced Self-Assembly of Surfactants at the Solid-Aqueous Interface Curr. Opin. Colloid Interface Sci. 1999, 4, 411-419 10.1016/S1359-0294(00)00016-9
48. Becraft, K. a; Moore, F. G.; Richmond, G. L. In-Situ Spectroscopic Investigations of Surfactant Adsorption and Water Structure at the CaF2/aqueous Solution Interface Phys. Chem. Chem. Phys. 2004, 6, 1880-1889 10.1039/b313513f
49. Liu, C.-H.; Chuang, Y.-H.; Chen, T.-Y.; Tian, Y.; Li, H.; Wang, M.-K.; Zhang, W. Mechanism of Arsenic Adsorption on Magnetite Nanoparticles from Water: Thermodynamic and Spectroscopic Studies Environ. Sci. Technol. 2015, 49, 7726-7734 10.1021/acs.est.5b00381
50. Lee, K. E.; Gomez, M. a.; Elouatik, S.; Demopoulos, G. P. Further Understanding of the Adsorption Mechanism of N719 Sensitizer on Anatase TiO2 Films for DSSC Applications Using Vibrational Spectroscopy and Confocal Raman Imaging Langmuir 2010, 26, 9575-9583 10.1021/la100137u
51. Velasco, L. F.; Ania, C. O. Understanding Phenol Adsorption Mechanisms on Activated Carbons Adsorption 2011, 17, 247-254 10.1007/s10450-011-9322-x
52. Tripathi, A.; Emmons, E. D.; Christesen, S. D.; Fountain, A. W.; Guicheteau, J. A. Kinetics and Reaction Mechanisms of Thiophenol Adsorption on Gold Studied by Surface-Enhanced Raman Spectroscopy J. Phys. Chem. C 2013, 117, 22834-22842 10.1021/jp407105v
53. Guan, X. H.; Chen, G. H.; Shang, C. ATR-FTIR and XPS Study on the Structure of Complexes Formed upon the Adsorption of Simple Organic Acids on Aluminum Hydroxide J. Environ. Sci. 2007, 19, 438-443 10.1016/S1001-0742(07)60073-4
54. Gao, X.; Chorover, J. Adsorption of Perfluorooctanoic Acid and Perfluorooctanesulfonic Acid to Iron Oxide Surfaces as Studied by Flow-through ATR-FTIR Spectroscopy Environ. Chem. 2012, 9, 148-157 10.1071/EN11119
55. Ito, Y.; Virkar, A. a; Mannsfeld, S.; Oh, J. H.; Toney, M. et al. Crystalline Ultra Smooth Self-Assembled Monolayers of Alkylsilanes for Organic Field-Effect Transistors SI J. Am. Chem. Soc. 2009, 131, 9396-9404 10.1021/ja9029957
56. Schönherr, H.; Ringsdorf, H. Self-Assembled Monolayers of Symmetrical and Mixed Alkyl Fluoroalkyl Disulfides on Gold. 1. Synthesis of Disulfides and Investigation of Monolayer Properties Langmuir 1996, 12, 3891-3897 10.1021/la9601418
57. Viana, A. S.; Abrantes, L. M.; Jin, G.; Floate, S.; Nichols, R. J.; Kalaji, M. Electrochemical, Spectroscopic and SPM Evidence for the Controlled Formation of Self-Assembled Monolayers and Organised Multilayers of Ferrocenyl Alkyl Thiols on Au (111) Phys. Chem. Chem. Phys. 2001, 3, 3411-3419 10.1039/b101435h
58. Mohamed, M. H.; Wilson, L. D.; Headley, J. V. Design and Characterization of Novel β-Cyclodextrin Based Copolymer Materials Carbohydr. Res. 2011, 346, 219-229 10.1016/j.carres.2010.11.022
59. Brunauer, S.; Emmett, P. H.; Teller, E. Gases I N Multimolecular Layers J. Am. Chem. Soc. 1938, 60, 309-319 10.1021/ja01269a023
60. Gupta, A.; Mandal, S.; Katiyar, M.; Mohapatra, Y. N. Film Processing Characteristics of Nano Gold Suitable for Conductive Application on Flexible Substrates Thin Solid Films 2012, 520, 5664-5670 10.1016/j.tsf.2012.04.017
61. Langmuir, I. The Constitution and Fundamental Properties of Solids and Liquids. Part I. Solids J. Am. Chem. Soc. 1916, 38, 2221 10.1021/ja02268a002
62. Gauglitz, G.; Vo-Dinh, T. Handbook of Spectroscopy; Wiley-VCH Verlag GMbH & Co. KGaA: Weinheim, 2013.
63. Vlachy, N.; Jagoda-Cwiklik, B.; Vácha, R.; Touraud, D.; Jungwirth, P.; Kunz, W. Hofmeister series and specific interactions of charged headgroups with aqueous ions Adv. Colloid Interface Sci. 2009, 146, 42-47 and references cited therein. 10.1016/j.cis.2008.09.010
64. Jing, P.; Rodgers, P. J.; Amemiya, S. High Lipophilicity of Perfluoroalkyl Carboxylate and Sulfonate: Implications for Their Membrane Permeability J. Am. Chem. Soc. 2009, 131, 2290-2296 10.1021/ja807961s
65. Levitz, P. Aggregative Adsorption of Nonionic Surfactants onto Hydrophilic Soid/Water Interface. Relation with Bulk Micellization Langmuir 1991, 7, 1595-1608 10.1021/la00056a010
66. Mohamed, M. H.; Wilson, L. D.; Headley, J. V. Estimation of the Surface Accessible Inclusion Sites of β-Cyclodextrin Based Copolymer Materials Carbohydr. Polym. 2010, 80, 186-196 10.1016/j.carbpol.2009.11.014
67. EPA. EmergingContaminants-Perfluorooctane Sulfonate (PFOS) and PerfluorooctanoicAcid (PFOA) At a Glance. (2012, No. May, 6.
68. Hoffmann, H.; Würtz, J. Unusual Phenomena in Perfluorosurfactants J. Mol. Liq. 1997, 72, 191-230 10.1016/S0167-7322(97)00039-1
69. Li, M.-H. Toxicity of Perfluorooctane Sulfonate and PErfluorooctanoic Acid to Plants and Aquatic Invertebrates Environ. Toxicol. 2009, 24, 95-101 10.1002/tox.20396
70. CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2005.
71. Mohamed, M. H.; Wilson, L. D.; Headley, J. V.; Peru, K. M. Investigation of the Sorption Properties of β-Cyclodextrin-Based Polyurethanes with Phenolic Dyes and Naphthenates J. Colloid Interface Sci. 2011, 356, 217-226 10.1016/j.jcis.2010.11.002
72. Guo, W.; Fung, B. M.; Christian, S. D. NMR Study of Cyclodextrin Inclusion of Fluorocarbon Surfactants in Solution Langmuir 1992, 8, 446-451 10.1021/la00038a022
73. Eissa, A. S.; Khan, S. A. Modulation of Hydrophobic Interactions in Denatured Whey Proteins by Transglutaminase Enzyme Food Hydrocolloids 2006, 20, 543-547 10.1016/j.foodhyd.2005.07.005
74. Tu, A.; Kwag, H. R.; Barnette, A. L.; Kim, S. H. Water Adsorption Isotherms on CH3-, OH-, and COOH-Terminated Organic Surfaces at Ambient Conditions Measured with PM-RAIRS Langmuir 2012, 28, 15263-15269 10.1021/la302848k
75. Sing, K. S. W. Reporting Physisorption Data for Gas/solid Systems with Special Reference to the Determination of Surface Area and Porosity (Recommendations 1984) Pure Appl. Chem. 1985, 57, 603-619 10.1351/pac198557040603
76. Zhang, Y.; Cremer, P. S. Interactions between macromolecules and ions: the Hofmeister series Curr. Opin. Chem. Biol. 2006, 10, 658-663 10.1016/j.cbpa.2006.09.020
77. García-Zubiri, I. X.; González-Gaitano, G.; Isasi, J. R. Sorption Models in Cyclodextrin Polymers: Langmuir, Freundlich, and a Dual-Mode Approach J. Colloid Interface Sci. 2009, 337, 11-18 10.1016/j.jcis.2009.04.071
78. Ito, K.; Yoshida, K.; Ujimoto, K.; Yamaguchi, T. Thermal Behavior and Structure of Low-Temperature Water Confined in Sephadex G15 Gel by Differential Scanning Calorimetry and X-Ray Diffraction Method Anal. Sci. 2013, 29, 353-359 10.2116/analsci.29.353
79. Mathlouthi, M. Water Content, Water Activity, Water Structure and the Stability of Foodstuffs Food Control 2001, 12, 409-417 10.1016/S0956-7135(01)00032-9
80. Ping, Z. H.; Nguyen, Q. T.; Chen, S. M.; Zhou, J. Q.; Ding, Y. D. States of Water in Different Hydrophilic Polymers-DSC and FTIR Studies Polymer 2001, 42, 8461-8467 10.1016/S0032-3861(01)00358-5
81. Knowlton, G. D. Thermal Study of Types of Water Associated with Clinoptilolite Clays Clay Miner. 1981, 29, 403-411 10.1346/CCMN.1981.0290510
82. Volkov, V. V.; Nuti, F.; Takaoka, Y.; Chelli, R.; Papini, A. M.; Righini, R. Hydration and Hydrogen Bonding of Carbonyls in Dimyristoyl-Phosphatidylcholine Bilayer J. Am. Chem. Soc. 2006, 128, 9466-9471 10.1021/ja0614621
83. Wang, R.; Wang, Q.; Li, L. Evaporation Behaviour of Water and Its Plasticizing Effect in Modified Poly(vinyl Alcohol) Systems Polym. Int. 2003, 52, 1820-1826 10.1002/pi.1385
84. Kohler, K.; Mohwald, H.; Sukhorukov, G. B.; Ko, K. Thermal Behavior of Polyelectrolyte Multilayer Microcapsules: 2. Insight into Molecular Mechanisms for the PDADMAC/PSS System Thermal Behavior of Polyelectrolyte Multilayer Microcapsules J. Phys. Chem. B 2006, 110, 24002-24010 10.1021/jp062907a
85. Schönhoff, M.; Ball, V.; Bausch, A. R.; Dejugnat, C.; Delorme, N.; Glinel, K.; Klitzing, R. V.; Steitz, R. Hydration and Internal Properties of Polyelectrolyte Multilayers Colloids Surf., A 2007, 303, 14-29 10.1016/j.colsurfa.2007.02.054
86. Meier, M. M.; Luiz, M. T. B.; Szpoganicz, B.; Soldi, V. Thermal Analysis Behavior of B- and G-Cyclodextrin Inclusion Complexes with Capric and Caprilic Acid Thermochim. Acta 2001, 375, 153-160 10.1016/S0040-6031(01)00514-7
87. Yilgor, E.; Yilgor, I.; Yurtsever, E. Hydrogen Bonding and Polyurethane Morphology. I. Quantum Mechanical Calculations of Hydrogen Bond Energies and Vibrational Spectroscopy of Model Compounds Polymer 2002, 43, 6551-6559 10.1016/S0032-3861(02)00567-0
88. Meaurio, E.; Cesteros, L. C.; Katime, I. FTIR Study of Hydrogen Bonding of Blends of Poly(mono N-Alkyl Itaconates) with Poly(N,N-Imethylacrylamide) and Poly(ethyloxazoline) Macromolecules 1997, 30, 4567-4573 10.1021/ma970115w
89. Shinde, S. S.; Patil, S. S.; Mevekari, F. I.; Satpute, A. S. An Approach for Solubility Enhancement: Solid Dispersion Int. J. Adv. Pharm. Sci. 2010, 1, 299-308
90. Joseph, J.; Jemmis, E. D. Red-, Blue, or No-Shift in Hydrogen Bonds: A Unified Explanation J. Am. Chem. Soc. 2007, 129, 4620-4632 10.1021/ja067545z
91. Sari, A.; Akcay, M.; Soylak, M.; Onal, A. Polymer-Stearic Acid Blends as Form-Stable Phase Change Material for Thermal Energy Storage J. Sci. Ind. Res. (India) 2005, 64, 991-996
92. Shakirova, L.; Grube, M.; Goodacre, R.; Gavare, M.; Auzina, L.; Zikmanis, P. FT-IR Spectroscopic Investigation of Bacterial Cell Envelopes from Zymomonas Mobilis Which Have Different Surface Hydrophobicities Vib. Spectrosc. 2013, 64, 51-57 10.1016/j.vibspec.2012.10.008
93. Max, J. J.; Chapados, C. Infrared Spectroscopy of Aqueous Carboxylic Acids: Comparison between Different Acids and Their Salts J. Phys. Chem. A 2004, 108, 3324-3337 10.1021/jp036401t
94. Arkles, B. Hydrophobicity, Hydrophilicity, and Silanes; Gelest Inc.: Morrisville, PA, October 2006; p 10.
95. Tavana, H.; Hair, M. L.; Neumann, a. W. Influence of Electronic Properties of Naphthalene Compounds on Contact Angles J. Phys. Chem. B 2006, 110, 1294-1300 10.1021/jp0548063
96. Bouchemal, K.; Mazzaferro, S. How to Conduct and Interpret ITC Experiments Accurately for Cyclodextrin-Guest Interactions Drug Discovery Today 2012, 17, 623-629 10.1016/j.drudis.2012.01.023
97. Wszelaka-Rylik, M.; Gierycz, P. Isothermal Titration Calorimetry (ITC) Study of Natural Cyclodextrins Inclusion Complexes with Drugs J. Therm. Anal. Calorim. 2013, 111, 2029-2035 10.1007/s10973-012-2251-4
98. Parker, K. M.; Stalcup, A. M. Affinity Capillary Electrophoresis and Isothermal Titration Calorimetry for the Determination of Fatty Acid Binding with Beta-Cyclodextrin J. Chromatogr. A 2008, 1204, 171-182 10.1016/j.chroma.2008.02.050
99. Cooper, A.; Johnson, C. M.; Lakey, J. H.; Nöllmann, M. Heat Does Not Come in Different Colours: Entropy-Enthalpy Compensation, Free Energy Windows, Quantum Confinement, Pressure Perturbation Calorimetry, Solvation and the Multiple Causes of Heat Capacity Effects in Biomolecular Interactions Biophys. Chem. 2001, 93, 215-230 10.1016/S0301-4622(01)00222-8
100. Dunitz, J. D. Win Some, Lose Some: Enthalpy-Entropy Compensation in Weak Intermolecular Interactions Chem. Biol. 1995, 2, 709-712 10.1016/1074-5521(95)90097-7
101. Blokzijl, B. W.; Engberts, J. B. F. N. Hydrophobic Effects. Opinions and Facts Angew. Chem., Int. Ed. Engl. 1993, 32, 1545-1579 10.1002/anie.199315451