Micellar Encapsulation of Some Polycyclic Aromatic Hydrocarbons by Glucose Derived Non-Ionic Gemini Surfactants in Aqueous Medium

Abstract Novel glucose-based non-ionic gemini surfactants consisting of two sugar head groups, two hydrophobic tails having chain length of C8, C10, C12, C14, C16, C18 and –CH2-C6H4-CH2– as a rigid spacer were synthesized and investigated for their micellar encapsulation properties. The head groups of the geminis consist of glucose entities (with reducing function blocked in cyclic acetal group) connected through C-6 to tertiary amines. These surfactants were explored for micellar encapsulation of some polynuclear aromatic hydrocarbons (PAHs) viz. fluorene, anthracene, triptycene and pyrene in 20% ethanol–water mixture. Micellar studies revealed that PAHs were encapsulated in the sequence fluorene > anthracene > triptycene > pyrene and the better efficiency of gemini surfactant was dependent on longer alkyl tail but lesser HLB value.

[1]  M. Ilies,et al.  Heterocyclic Cationic Gemini Surfactants: A Comparative Overview of Their Synthesis, Self‐assembling, Physicochemical, and Biological Properties , 2014, Medicinal research reviews.

[2]  A. I. Mohammed,et al.  Synthesis of D-mannitol substituted ether-linked bis-1,2,3-triazoles as models of gemini surfactants , 2012 .

[3]  Saroj,et al.  Novel glucose derived non-ionic gemini surfactants as reverse micellar systems for encapsulation of d- and l-enantiomers of some aromatic α-amino acids in n-hexane , 2012, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[4]  K. Wilk,et al.  Fluorescence probe studies upon microenvironment characteristics and aggregation properties of gemini sugar surfactants in an aquatic environment , 2011 .

[5]  Yilin Wang,et al.  Aggregation behavior of gemini surfactants and their interaction with macromolecules in aqueous solution. , 2011, Physical chemistry chemical physics : PCCP.

[6]  K. Sakai,et al.  Recent advances in gemini surfactants: oleic Acid-based gemini surfactants and polymerizable gemini surfactants. , 2011, Journal of oleo science.

[7]  Christian J. Petropolis,et al.  Synthesis of surfactants based on pentaerythritol. I. Cationic and zwitterionic gemini surfactants. , 2009, The Journal of organic chemistry.

[8]  C. Bombelli,et al.  Gemini surfactant based carriers in gene and drug delivery. , 2009, Current medicinal chemistry.

[9]  Uri Zoller,et al.  Handbook of Detergents, Part F : Production , 2008 .

[10]  K. Sakai,et al.  Adsorption characteristics of sugar-based monomeric and gemini surfactants at the silica/aqueous solution interface , 2008 .

[11]  K. Sakai,et al.  Adsorption and micellization behavior of novel gluconamide-type gemini surfactants. , 2008, Journal of colloid and interface science.

[12]  J. Engberts,et al.  Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer , 2007 .

[13]  I. Maliszewska,et al.  Novel glucose-derived gemini surfactants with a 1,1′-ethylenebisurea spacer: Preparation, thermotropic behavior, and biological properties , 2006 .

[14]  J. Barrowman,et al.  Polycyclic hydrocarbon and polychlorinated biphenyl solubilization in aqueous solutions of mixed micelles , 1983, Lipids.

[15]  Tomokazu Yoshimura,et al.  Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups. 1. Adsorption and micellization. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[16]  S. Warwel,et al.  Glucamine-based gemini surfactants I: Gemini surfactants from long-chain N-alkyl glucamines and α,ω-diepoxides , 2004 .

[17]  Gaoyong Zhang,et al.  Synthesis and characterization of glucosamide-based trisiloxane gemini surfactants , 2004 .

[18]  K. Wilk,et al.  Surface and micellar properties of new nonionic gemini aldonamide-type surfactants. , 2004, Journal of colloid and interface science.

[19]  M. Yoshimoto,et al.  Preparation of gemini-type amphiphiles bearing cyclitol head groups and their application as high-performance modifiers for lipases. , 2004, Carbohydrate research.

[20]  Beata W. Domagalska,et al.  Aldonamide-type gemini surfactants: Synthesis, structural analysis, and biological properties , 2002 .

[21]  J. Kovensky,et al.  New Family of Nonionic Gemini Surfactants. Determination and Analysis of Interfacial Properties , 2002 .

[22]  A. Kremer,et al.  Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro. , 2001, European journal of biochemistry.

[23]  F. Menger,et al.  Gemini surfactants with a disaccharide spacer. , 2001, Journal of the American Chemical Society.

[24]  S. Blanco,et al.  UV Spectral Properties of Benzophenone. Influence of Solvents and Substituents , 2000 .

[25]  J. Kovensky,et al.  New dimeric surfactants from alkyl glucosides , 1999 .

[26]  Chunli Gao,et al.  Enzymatic synthesis of dimeric and trimeric sugar-fatty acid esters , 1999 .

[27]  Chunli Gao,et al.  Regioselective synthesis of dimeric (gemini) and trimeric sugar-based surfactants , 1999 .

[28]  J. Engberts,et al.  Nonionic bolaamphiphiles and gemini surfactants based on carbohydrates , 1997 .

[29]  J. Kovensky,et al.  Gemini surfactants from alkyl glucosides , 1997 .

[30]  L. Sharma,et al.  Synthesis, characterization, and reverse-micellar studies of some N-substituted derivatives of 6-amino-6-deoxy-1,2-O-isopropylidene-d-glucose , 1995 .

[31]  F. Menger,et al.  Hyperextended amphiphiles. Bilayer formation from single-tailed compounds , 1993 .

[32]  Y. Talmon,et al.  Dependence of aggregate morphology on structure of dimeric surfactants , 1993, Nature.

[33]  M. J. Rosen GEMINIS : A NEW GENERATION OF SURFACTANTS : THESE MATERIALS HAVE BETTER PROPERTIES THAN CONVENTIONAL IONIC SURFACTANTS AS WELL AS POSITIVE SYNERGISTIC EFFECTS WITH NON-IONICS , 1993 .

[34]  D. Vyas,et al.  Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles , 1975 .

[35]  A. Tracey,et al.  Conformational Studies on the 1,2;5,6-Di-O-isopropylidene-D-hexoses , 1972 .

[36]  C. A. Bunton,et al.  Specific salt effects upon the rates of SN1 solvolyses , 1971 .

[37]  W. Gratzer,et al.  Effect of protein denaturation on micelle stability. , 1969, The Journal of physical chemistry.

[38]  A. Parker,et al.  The Scission Of The Sulfur-Sulfur Bond , 1959 .