Cationic Gemini surfactants based on adamantane: Synthesis, surface activity and aggregation properties

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 441, Issue , 2014, Pages 572-580

  Zhong, Xing ^a   Guo, Jianwei ^a   Feng, Lijuan ^a   Xu, Xiaojian ^a   Zhu, Dongyu ^a  

^a GUANGDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Adamantane; Aggregation number; Micellization thermodynamics; Rigid spacer; Synthesis

Indexed keywords

CRITICAL MICELLE CONCENTRATION; DYNAMIC LIGHT SCATTERING; ELECTRIC CONDUCTIVITY; FLUORESCENCE; MICELLIZATION; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

ADAMANTANES; AGGREGATION NUMBERS; CATIONIC GEMINI SURFACTANT; CRITICAL MICELLE CONCENTRATION (CMC); ELECTRICAL CONDUCTIVITY MEASUREMENTS; FLUORESCENCE MEASUREMENTS; MICELLE AGGREGATION NUMBERS; RIGID SPACER;

AGGLOMERATION;

ADAMANTANE; CATIONIC GEMINI SURFACTANT; SURFACTANT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRITICAL MICELLE CONCENTRATION; DYNAMIC LIGHT SCATTERING; ELECTRIC CONDUCTIVITY; ENTHALPY; ENTROPY; FLUORESCENCE; LIGHT SCATTERING; LIPOPHILICITY; MICELLIZATION; PRIORITY JOURNAL; SURFACE PROPERTY; SURFACE TENSION; SYNTHESIS; THERMODYNAMICS;

EID: 84886680237     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2013.10.016     Document Type: Article

References (56)

1. Menger F.M., Keiper J.S. Gemini surfactants. Angew. Chem. Int. Ed. 2000, 39:1906-1920.
2. Zana R. Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review. Adv. Colloid Interface Sci. 2002, 97:205-253.
3. Menger F.M., Littau C.A. Gemini-surfactants: synthesis and properties. J. Am. Chem. Soc. 1991, 113:1451-1452.
4. Menger F.M., Littau C.A. Gemini surfactants: a new class of self-assembling molecules. J. Am. Chem. Soc. 1993, 115:10083-10090.
5. Esumi K., Goino M., Koide Y. Adsorption and adsolubilization by monomeric, dimeric, or trimeric quaternary ammonium surfactant at silica/water interface. J. Colloid Interface Sci. 1996, 183:539-545.
6. Ali M.S., Suhail M., Ghosh G., Kamil M., Din K.U. Interactions between cationic gemini/conventional surfactants with polyvinylpyrrolidone: specific conductivity and dynamic light scattering studies. Colloids Surf. A: Physicochem. Eng. Aspects 2009, 350:51-56.
7. Rosen M.J., Mathias J.H., Davenport L. Aberrant aggregation behavior in cationic gemini surfactants investigated by surface tension, interfacial tension, and fluorescence methods. Langmuir 1999, 15:7340-7346.
8. Wang X.Y., Wang J.B., Wang Y.L., Yan H., Li P.X., Thomas R.K. Effect of the nature of the spacer on the aggregation properties of gemini surfactants in an aqueous solution. Langmuir 2004, 20:53-56.
9. Menger F.M., Keiper J.S., Azov V. Gemini surfactants with acetylenic spacers. Langmuir 2000, 16:2062-2067.
10. Han Y.C., Wang Y.L. Aggregation behavior of gemini surfactants and their interaction with macromolecules in aqueous solution. Phys. Chem. Chem. Phys. 2011, 13:1939-1956.
11. Zhu D.Y., Cheng F., Chen Y., Jiang S.C. Preparation, characterization and properties of anionic gemini surfactants with long rigid or semi-rigid spacers. Colloids Surf. A: Physicochem. Eng. Aspects 2012, 397:1-7.
12. Sikirić M., Primožič I., Talmon Y., Filipović-Vinceković N. Effect of the spacer length on the association and adsorption behavior of dissymmetric gemini surfactants. J. Colloid Interface Sci. 2005, 281:473-481.
13. Tehrani-Bagha A.R., Kärnbratt J., Löfroth J.E., Holmberg K. Cationic ester-containing gemini surfactants: determination of aggregation numbers by time-resolved fluorescence quenching. J. Colloid Interface Sci. 2012, 376:126-132.
14. Czechura K., Sayari A. Synthesis of MCM-48 silica using a gemini surfactant with a rigid spacer. Chem. Mater. 2006, 18:4147-4150.
15. Zhang G., Liu M. Interfacial assemblies of cyanine dyes and gemini amphiphiles with rigid spacers: regulation and interconversion of the aggregates. J. Phys. Chem. B 2008, 112:7430-7437.
16. Zhang Z.G., Zheng P.Z., Guo Y.M., Yang Y., Chen Z.Y., Wang X.Y., An X.Q. The effect of the spacer rigidity on the aggregation behavior of two ester-containing Gemini surfactants. J. Colloid Interface Sci. 2012, 379:64-71.
17. Zhu S., Liu L.J., Cheng F. Influence of spacer nature on the aggregation properties of anionic gemini surfactants in aqueous solutions. J. Surfactant Deterg. 2011, 14:221-225.
18. Zhou M., Liu H.L., Yang H.F., Liu X.L., Zhang Z.R., Hu Y. Spontaneous crystallization at the air-water interface: an unusual feature of gemini surfactant with a rigid spacer. Langmuir 2006, 22:10877-10879.
19. Mivehi L., Bordes R., Holmberg K. Adsorption of cationic gemini surfactants at solid surfaces studied by QCM-D and SPR: effect of the rigidity of the spacer. Langmuir 2011, 27:7549-7557.
20. Rosen M.J., Song L.D. Dynamic surface tension of aqueous surfactant solutions 8. Effect of spacer on dynamic properties of gemini surfactant solutions. J. Colloid Interface Sci. 1996, 179:261-268.
21. Xie D.H., Zhao J. Unique aggregation behavior of a carboxylate gemini surfactant with a long rigid spacer in aqueous solution. Langmuir 2013, 29:545-553.
22. Eastoe J., Dominguez M.S., Wyatt P., Beeby A., Heenan R.K. Properties of a stilbene-containing gemini photosurfactant: light-triggered changes in surface tension and aggregation. Langmuir 2002, 18:7837-7844.
23. Fort R.C., Schleyer P.R. Adamantane: consequences of the diamondoid structure. Chem. Rev. 1964, 64:277-300.
24. Hu Y., Sinnot S.B. A molecular dynamics study of thin-film formation via molecular cluster beam deposition: effect of incident species. Surf. Sci. 2003, 526:230-242.
25. Bauer L., Khullar K.K. Carbon-sulfur cleavage of 1-adamantyl sulfides. J. Org. Chem. 1971, 36:3038-3040.
26. Azzam W., Bashir A., Shekhah O. Thermal study and structural characterization of self-assembled monolayers generated from diadamantane disulfide on Au (111). Appl. Surf. Sci. 2011, 257:3739-3747.
27. Halimehjani A.Z., Marjani K., Ashouri A., Amani V. Synthesis and characterization of transition metal dithiocarbamate derivatives of 1-aminoadamantane: crystal structure of (N-adamantyldithiocarbamato)nickel(II). Inorg. Chim. Acta 2011, 373:282-285.
28. Vashkevich E.V., Yurashevich N.Y., Kozlov N.G., Potkin V.I., Potkina T.N. Synthesis of surfactants derived from adamantane. Russ. J. Appl. Chem. 2001, 74:1892-1898.
29. Migulin V.A., Menger F.M. Adamantane-based crystals with rhythmic morphologies. Langmuir 2001, 17:1324.
30. Guo J.W., Zhong X., Zhu H., Feng L.J., Cui Y.D. Synthesis of novel quaternary ammonium surfactants containing adamantane. Chin. Chem. Lett. 2012, 23:653-656.
31. Butenko L.N., Protopopov P.A., Derbisher V.E., Khardin A.P. Synthesis of functional derivatives of tricyclic hydrocarbons. Synth. Commun. 1984, 14:113-119.
32. Para G., Hamerska-Dudra A., Wilk K.A., Warszyński P. Surface activity of cationic surfactants, influence of molecular structure. Colloids Surf. A: Physicochem. Eng. Aspects 2010, 365:215-221.
33. Para G., Hamerska-Dudra A., Wilk K.A., Warszyński P. Mechanism of cationic surfactant adsorption-Effect of molecular structure and multiple charge. Colloids Surf. A: Physicochem. Eng. Aspects 2011, 383:67-72.
34. Zhang Q., Gao Z.N., Xu F., Tai S.X., Liu X.G., Mo S.B., Niu F. Surface tension and aggregation properties of novel cationic gemini surfactants with diethylammonium headgroups and a diamido spacer. Langmiur 2012, 28:11979-11987.
35. Wegrzynska J., Para G., Chlebicki J., Warszynski P., Wilk K.A. Adsorption of multiple ammonium salts at the air/solution interface. Langmuir 2008, 24:3171-3180.
36. Yoshimura T., Kusano T., Iwase H., Shibayama M., Ogawa T., Kurata H. Star-shaped trimeric quaternary ammonium bromide surfactants: adsorption and aggregation properties. Langmuir 2012, 28:9322-9331.
37. Shi L.J., Li N., Yan H., Gao Y.A., Zheng L.Q. Aggregation behavior of long-chain N-aryl imidazolium bromide in aqueous solution. Langmuir 2011, 27:1618-1625.
38. Inoue T., Ebina H., Dong B., Zheng L. Electrical conductivity study on micelle formation of long-chain imidazolium ionic liquids in aqueous solution. J. Colloid Interface Sci. 2007, 314:236-241.
39. Zhao M., Zheng L. Micelle formation by N-alkyl-N-methylpyrrolidinium bromide in aqueous solution. Phys. Chem. Chem. Phys. 2011, 13:1332-1337.
40. Mosquera V., del Río J.M., Attwood D., García M., Jones M.N., Prieto G., Suarez M.J., Sarmiento F. A study of the aggregation behavior of hexyltrimethylammonium bromide in aqueous solution. J. Colloid Interface Sci. 1998, 206:66-76.
41. Chen L.J., Lin S.Y., Huang C.C. Effect of hydrophobic chain length of surfactants on enthalpy-entropy compensation of micellization. J. Phys. Chem. B 1998, 102:4350-4356.
42. Song Y.B., Li Q.X., Li Y.L., Zhi L.F. Surface and aggregation properties of heterogemini surfactants containing quaternary ammonium and guanidine moiety. Colloids Surf. A: Physicochem. Eng. Aspects 2013, 417:236-242.
43. Quagliotto P., Viscardi G., Barolo C., Barni E., Bellinvia S., Fisicaro E., Compari C. Gemini pyridinium surfactants: synthesis and conductometric study of a novel class of amphiphiles. J. Org. Chem. 2003, 68:7651-7660.
44. Nusselder J.J.H., Engberts J.B.F.N. Toward a better understanding of the driving force for micelle formation and micellar growth. J. Colloid Interface Sci. 1992, 148:353-361.
45. Zhang Q., Gao Z.N., Xu F., Tai S.X. Effect of hydrocarbon structure of the headgroup on the thermodynamic properties of micellization of cationic gemini surfactants: an electrical conductivity study. J. Colloid Interface Sci. 2012, 371:73-81.
46. Zana R. Critical micellization concentration of surfactants in aqueous solution and free energy of micellization. Langmuir 1996, 12:1208-1211.
47. Grosmaire L., Chorro M., Chorro C., Partyka S., Zana R. Alkanediyl-α,ω-bis (dimethylalkylammonium bromide) surfactants: 9. Effect of the spacer carbon number and temperature on the enthalpy of micellization. J. Colloid Interface Sci. 2002, 246:175-181.
48. Blokzijl W., Engberts J.B.F.N. Hydrophobic effects. Opinions and facts. Angew. Chem. Int. Ed. Engl. 1993, 32:1545-1579.
49. Wilk K.A., Laska U., Zielińska K., Olszowski A. Fluorescence probe studies upon microenvironment characteristics and aggregation properties of gemini sugar surfactants in an aquatic environment. J. Photochem. Photobiol. A 2011, 219:204-210.
50. De S., Aswal V.K., Goyal P.S., Bhattacharya S. Novel gemini micelles from dimeric surfactants with oxyethylene spacer chain. Small angle neutron scattering and fluorescence studies. J. Phys. Chem. B 1998, 102:6152-6160.
51. Zana R., Levy H., Papoutsi D., Beinert G. Micellization of two triquaternary ammonium surfactants in aqueous solution. Langmuir 1995, 11:3694-3698.
52. Zhang Z., Wang H., Zheng P., Shen W. Effect of spacer rigidity on the aggregations of ester containing Gemini surfactants in aqueous solutions: a study of density and fluorescence. Colloids Surf. A: Physicochem. Eng. Aspects 2013, 421:193-200.
53. Turro N.J., Yekta A. Luminescent probes for detergent solutions. A simple procedure for determination of the mean aggregation number of micelles. J. Am. Chem. Soc. 1978, 100:5951-5952.
54. Malliaris A. Static fluorescence quenching in the study of micellar systems. Progr. Colloid Polym. Sci. 1987, 73:161-166.
55. Huang X., Han Y., Wang Y., Cao M., Wang Y. Aggregation properties of cationic gemini surfactants with dihydroxyethylamino headgroups in aqueous solution. Colloids Surf. A: Physicochem. Eng. Aspects 2008, 325:26-32.
56. Pedersen J.S., Egelhaaf S.U., Schurtenberger P. Formation of polymerlike mixed micelles and vesicles in lecithin-bile salt solutions: a small-angle neutron-scattering study. J. Phys. Chem. 1995, 99:1299-1305.