Synthesis and Characterization of Some Nonionic Bolaamphiphiles

Journal of Surfactants and Detergents - Tập 17 - Trang 1125-1131 - 2014
Ali Khalfallah1, Abdelhamid Ayari1, Abdelkader Kriaa1, Ahmed Hedhli1
1Laboratoire de Chimie Moléculaire Organique, Ecole Supérieure des Sciences et Techniques de Tunis, Tunis, Tunisia

Tóm tắt

A series of nonionic bolaamphiphiles were synthesized from the reaction of fluoroalkylene (dimercaptoacetates) with maleate crown ethers. Surface activity of the new surfactants was evaluated on the basis of surface tension measurements. The new fluorinated bolamphiphiles exhibit a remarkable lowering of surface tension in comparison with nonfluorinated analogues.

Tài liệu tham khảo

Fuhrho JH, Fritsch D (1986) Bolaamphiphiles form ultrathin, porous and unsymmetric monolayer lipid membranes. Acc Chem Res 19:130–137 Fuhrhop JH, David HH, Mathieu J, Liman U, Winter HJ, Boekema E (1986) Bolaamphiphiles and monolayer lipid membranes made from 1,6,19,24-tetraoxa-3,21-cyclohexatriacontadiene-2,5,20,23-tetrone. J Am Chem Soc 108:1785–1791 Lo Nostro P, Briganti G, Chen SH (1991) Structural properties of vesicles produced from a new bipolar lipid. J Coll Interf Sci 142:214–223 Satake I, Morita T, Maeda T, Hayakawa K (1997) The micellar properties of ionic surfactants consisting of the, ω-type surfactant ion and the same type counter ion. Bull Chem Soc Jpn 70:761–765 Zana R, Muto Y, Esumi K, Meguro K (1988) Mixed micelle formation between alkyltrimethylammonium bromide and alkane-α,ω-bis(trimethylammonium) bromide in aqueous. J Coll Interf Sci 123:502–511 Fuhrhop JH, Endisch C (2000) Molecular and supramolecular chemistry of natural products and model compounds. Marcel Decker, New York 606 Ulman A (1991) In: Jovanovich HB (ed) An introduction to ultrathin organic films, from Langmuir–Blodgett to self-assembly. Academic Press, New York Matsuda H, Yamada Y, Kanamori K, Kudo Y, Takeda Y (1991) On the facilitation effect of neutral macrocyclic ligands on the ion transfer across the interface between aqueous and organic solution, I. Theoretical equation of ion-transfer-polarographic current–potential curves and its experimental verification. Bull Chem Soc Jpn 64:1497–1508 Fyles TM, Zeng B (1998) Bolaamphiphiles promote phospholipid translocation across vesicle membranes. J Org Chem 63:8337–8345 Muzzalupo R, Nicoletta FP, Trombino S, Cassano R, Iemma F, Picci N (2007) A new crown ether as vesicular carrier for 5-fluorouracil: synthesis, characterization and drug delivery evaluation. Coll Surf B 58:197–202 Tavano L, Muzzalupo R, Trombino S, Nicotera I, Rossi CO, La Mesa C (2008) N, N′-Hexadecanoyl l-2-diaminomethyl-18-crown-6 surfactant: synthesis and aggregation features in aqueous solution. Coll Surf B 61:30–38 Fendler JH (1987) Atomic and molecular clusters in membrane mimetic chemistry. Chem Rev 87:877–899 Thuduppathy GR, Craig JW, Kholodenko V, Schon A, Hill RB (2006) Evidence that membrane insertion of the cytosolic domain of BCl-XL is governed by an electrostatic mechanism. J Mol Biol 395:1045–1058 Keller S, Heerklotz H, Blume AJ (2006) Monitoring lipid membrane translocation of sodium dodecyl sulfate by isothermal titration calorimetry. J Am Chem Soc 128:1279–1286 Schuy S, Faiss S, Yoder NC, Kalsani V, Kumar K, Janshoff A, Vogel R (2008) Structure and thermotropic phase behavior of fluorinated phospholipid bilayers: a combined attenuated total, reflection, FTIR spectroscopy, and imaging ellipsometry study. J Phys Chem B 112:8250–8256 Khalfallah A, Ayari A, Boughariaou B, Hedhli A (2010) Synthesis and surface-active properties of fluorinated cyclic PEGyl succinate derivatives. J Incl Phenom Macromol Chem 67:1–6 Khalfalla A, Boughariaou B, Hedhli A (2013) Synthesis and surface-active properties of F-alkylated polar loops. J Surfact Deterg 16:191–196 Essahli M, El Asri M, Boulahna A, Zenkouar M, Viguier M, Hervaud Y, Boutevin B (2006) New alkylated and perfluoroalkylated phosphonic acids: synthesis, adhesive and water-repellent properties on aluminum substrates. J Fluor Chem 127:854–860 Brace NO (2005) Reactions of 2-(perfluoroalkyl) ethane thiols with 1,6-heptadiene and substituted 1,6-heptadienes: the synthesis of RF ethanethio-cyclopentanoic and––dioic acids; and, ‘‘geminal twin-tail’’ bis-(perfluoroalkylethanethio) alkanoic acids. J Fluor Chem 126:7–15 Wathier M, Polidori A, Ruiz K, Fabiano A-S, Pucci B (2001) Synthèse et étude du comportement en milieu aqueux de tensioactifs gémini glycosylés. New J Chem 25:1588–1599 Jouani MA-E, Szönyi S, Dieng SY, Cambon A, Geribaldi S (1999) Synthesis and surface-active properties of new gemini surfactants with symmetrical perfluoroalkyl groups. New J Chem 23:557–562 De la Maza A, Lopez O, Cocera M, Coderch L, Parra JL (1999) Alkyl sulfate surfactants as solubilizing agents of liposomes modeling the composition of the stratum corneum lipids. Coll Surf A 147:341–348 Ikeda I, Ozawa Y, Nakatsuji Y, Okahara M (1987) Synthesis and surface properties of N-long chain alkyl dihydroxy monoazacrown ethers. J Am Oil Chem Soc 64:1034–1037 Tanford C (1980) The hydrophobic effect, 2nd edn. Wiley, New York Plehnert Schröter JA, Tschierske C (1998) Selective cationic binding at the air-water interface by thin films of rigid amphiphiles bearing laterally attached crown ether moieties. Langmuir 14:5245–5249 Nagawa Y, Regen S (1991) Membrane-disrupting surfactants that are highly selective toward lipid bilayers of varying cholesterol content. J Am Chem Soc 113:7237–7240