Solution properties and electrospinning of phosphonium gemini surfactants

Sean T. Hemp, Amanda G. Hudson, Michael H. Allen, Sandeep S. Pole, Robert B. Moore, Timothy Edward Long

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Bis(diphenylphosphino)alkanes quantitatively react with excess 1-bromododecane to prepare novel phosphonium gemini surfactants with spacer lengths ranging from 2 to 4 methylenes (12-2/3/4-12P). Dodecyltriphenylphosphonium bromide (DTPP), a monomeric surfactant analog, was readily water soluble, however, in sharp contrast, phosphonium gemini surfactants were poorly soluble in water due to two hydrophobic tails and relatively hydrophobic cationic head groups containing phenyl substituents. Isothermal titration calorimetry did not reveal a measurable critical micelle concentration for the 12-2-12P phosphonium gemini surfactant in water at 25 °C. Subsequent studies in 50/50 v/v water-methanol at 25 °C showed a CMC of 1.0 mM for 12-2-12P. All phosphonium gemini surfactants effectively complexed nucleic acids, but failed to deliver nucleic acids in vitro to HeLa cells. The solution behavior of phosphonium gemini surfactants was investigated in chloroform, which is an organic solvent where reverse micellar structures are favored. Solution rheology in chloroform explored the solution behavior of the phosphonium gemini surfactants compared to DTPP. The 12-2-12P and 12-3-12P gemini surfactants were successfully electrospun from chloroform to generate uniform fibers while 12-4-12P gemini surfactant and DTPP only electrosprayed to form droplets.

Original languageEnglish
Pages (from-to)3970-3977
Number of pages8
JournalSoft Matter
Volume10
Issue number22
DOIs
Publication statusPublished - 2014 Jun 14
Externally publishedYes

Fingerprint

Electrospinning
Surface-Active Agents
surfactants
Chloroform
chloroform
bromides
Water
nucleic acids
Nucleic Acids
water
Alkanes
Critical micelle concentration
Calorimetry
Titration
Rheology
rheology
titration
Organic solvents
spacers
alkanes

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Hemp, S. T., Hudson, A. G., Allen, M. H., Pole, S. S., Moore, R. B., & Long, T. E. (2014). Solution properties and electrospinning of phosphonium gemini surfactants. Soft Matter, 10(22), 3970-3977. https://doi.org/10.1039/c4sm00271g

Solution properties and electrospinning of phosphonium gemini surfactants. / Hemp, Sean T.; Hudson, Amanda G.; Allen, Michael H.; Pole, Sandeep S.; Moore, Robert B.; Long, Timothy Edward.

In: Soft Matter, Vol. 10, No. 22, 14.06.2014, p. 3970-3977.

Research output: Contribution to journalArticle

Hemp, ST, Hudson, AG, Allen, MH, Pole, SS, Moore, RB & Long, TE 2014, 'Solution properties and electrospinning of phosphonium gemini surfactants', Soft Matter, vol. 10, no. 22, pp. 3970-3977. https://doi.org/10.1039/c4sm00271g
Hemp ST, Hudson AG, Allen MH, Pole SS, Moore RB, Long TE. Solution properties and electrospinning of phosphonium gemini surfactants. Soft Matter. 2014 Jun 14;10(22):3970-3977. https://doi.org/10.1039/c4sm00271g
Hemp, Sean T. ; Hudson, Amanda G. ; Allen, Michael H. ; Pole, Sandeep S. ; Moore, Robert B. ; Long, Timothy Edward. / Solution properties and electrospinning of phosphonium gemini surfactants. In: Soft Matter. 2014 ; Vol. 10, No. 22. pp. 3970-3977.
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