Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction

Toshiaki Taira; Yuki Ishizaki; Kenichi Sakai; Hideki Sakai; Tomohiro Imura

doi:10.5650/jos.ess20106

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Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction

Toshiaki Taira, Yuki Ishizaki, Kenichi Sakai, Hideki Sakai, Tomohiro Imura

著者情報

キーワード: bolaamphiphile, phosphonic acid, surface activity, self-assembly

ジャーナルフリー早期公開

論文ID: ess20106

DOI https://doi.org/10.5650/jos.ess20106

この記事には本公開記事があります。

The final version of this article is now available: Vol. 69 (2020), No. 11 pp. 1437-1443

詳細

抄録

We report the synthesis of bolaamphiphilic alkenyl phosphonic acid (BPC₁₂) through the olefin cross-metathesis 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 D₂O up to 3.4 g L^–1, as confirmed by ¹H 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 (A) of BPC₁₂ (216 Å²) was ten times larger than that of dodecenyl phosphonic acid PC₁₂ (23 Å²). Moreover, dynamic light scattering measurement of an aqueous BPC₁₂ solution (5 mM) revealed the formation of large aggregates with an average estimated diameter of 81.8±27.0 nm.

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