Journal
JOURNAL OF OLEO SCIENCE
Volume 69, Issue 11, Pages 1437-1443Publisher
JAPAN OIL CHEMISTS SOC
DOI: 10.5650/jos.ess20106
Keywords
bolaamphiphile; phosphonic acid; surface activity; self-assembly
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Funding
- JSPS KAKENHI [JP 19K05194]
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We report the synthesis of bolaamphiphilic alkenyl phosphonic acid (BPC12) through the olefin crossmetathesis reaction of vinylphosphonic acid with 1,11-dodecadiene in the presence of a Ru-carbene catalyst. BPC12 possesses two trans-P-C=C moieties and is thus readily soluble in water up to 3.4 g L-1, as confirmed by H-1 nuclear magnetic resonance (NMR) measurements. Surface tension measurements revealed that BPC12 reduced the surface tension of water from 72.0 to 47.0 mN m(-1). The occupied area per molecule at the air/water interface (A) of BPC12 (216 angstrom(2)) was ten times larger than that of dodecenyl phosphonic acid PC12 (23 angstrom(2)). Moreover, dynamic light scattering measurement of an aqueous BPC12 solution (5 mM) revealed the formation of large aggregates with an average diameter of 81.8 +/- 27.0 nm.
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