Skip to main content
Log in

Synthesis and Characterization of Some Nonionic Bolaamphiphiles

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1

Similar content being viewed by others

References

  1. Fuhrho JH, Fritsch D (1986) Bolaamphiphiles form ultrathin, porous and unsymmetric monolayer lipid membranes. Acc Chem Res 19:130–137

    Article  Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. 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

    Article  CAS  Google Scholar 

  5. 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

    Article  CAS  Google Scholar 

  6. Fuhrhop JH, Endisch C (2000) Molecular and supramolecular chemistry of natural products and model compounds. Marcel Decker, New York 606

    Google Scholar 

  7. Ulman A (1991) In: Jovanovich HB (ed) An introduction to ultrathin organic films, from Langmuir–Blodgett to self-assembly. Academic Press, New York

    Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. Fyles TM, Zeng B (1998) Bolaamphiphiles promote phospholipid translocation across vesicle membranes. J Org Chem 63:8337–8345

    Article  CAS  Google Scholar 

  10. 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

    Article  CAS  Google Scholar 

  11. 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

    Article  CAS  Google Scholar 

  12. Fendler JH (1987) Atomic and molecular clusters in membrane mimetic chemistry. Chem Rev 87:877–899

    Article  CAS  Google Scholar 

  13. 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

    Article  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. Khalfalla A, Boughariaou B, Hedhli A (2013) Synthesis and surface-active properties of F-alkylated polar loops. J Surfact Deterg 16:191–196

    Article  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. 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

    Article  CAS  Google Scholar 

  20. 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

    Article  CAS  Google Scholar 

  21. 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

    Article  Google Scholar 

  22. 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

    Article  Google Scholar 

  23. 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

    Article  CAS  Google Scholar 

  24. Tanford C (1980) The hydrophobic effect, 2nd edn. Wiley, New York

    Google Scholar 

  25. 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

    Article  CAS  Google Scholar 

  26. 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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Ministry of Higher Education and Scientific Research Tunisia. We are grateful to Professor P. Dixneuf (University of Rennes1, France) for his spectroscopic facility.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ahmed Hedhli.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khalfallah, A., Ayari, A., Kriaa, A. et al. Synthesis and Characterization of Some Nonionic Bolaamphiphiles. J Surfact Deterg 17, 1125–1131 (2014). https://doi.org/10.1007/s11743-014-1602-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-014-1602-5

Keywords

Navigation