Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction
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...
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| Veröffentlicht in: | Journal of Oleo Science 2020, Vol.69(11), pp.1437-1443 |
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| container_issue | 11 |
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| container_title | Journal of Oleo Science |
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| creator | Taira, Toshiaki Ishizaki, Yuki Sakai, Kenichi Sakai, Hideki Imura, Tomohiro |
| description | 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 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 at the air/water interface (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 diameter of 81.8±27.0 nm. |
| doi_str_mv | 10.5650/jos.ess20106 |
| format | Article |
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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 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 at the air/water interface (A) of BPC12 (216 Å2) was ten times larger than that of dodecenyl phosphonic acid PC12 (23 Å2). 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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 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 at the air/water interface (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 diameter of 81.8±27.0 nm.</description><subject>Acids</subject><subject>bolaamphiphile</subject><subject>Chemical synthesis</subject><subject>Diameters</subject><subject>Metathesis</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>phosphonic acid</subject><subject>Phosphonic acids</subject><subject>Photon correlation spectroscopy</subject><subject>self-assembly</subject><subject>surface activity</subject><subject>Surface tension</subject><issn>1345-8957</issn><issn>1347-3352</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpFUEtP3DAQjqoilUJv_QGWem3Ab8dHumoBCQRa4Gx5nQlx6rW3cfaQ_nq8uzwkazwafy9PVX0n-ExIgc-HlM8gZ4oJlp-qY8K4qhkT9PO-F3WjhfpSfc15wLjMhTqunh_mOPWQfUapQxb9SsHa9ab35QTv0EX4C3EO6L5PedOnuBs536LVjJbb2tnJhvk_tOguQOcjWowpZ3QLk30VXYJ1k0_xtDrqbMjw7fU-qZ7-_H5cXNU3d5fXi4ub2pUfTLVuVh2HrnNUrbTEQjVCOe1wQxvaMsc4kZRIx4A62XKnmSKaMcmAFZKQDTupfhx0N2P6t4U8mSFtx1gsDeVCUYk51wX184Byu7wjdGYz-rUdZ0Ow2a2ysLJ5W2WBXx7ga2i9syHF4CN8KLeDSgEKg2KKDcZSE2IwoYZwpkrhJaLQJXtRWhyUhjzZZ3i3tePkXYC9rdSm0Et9839_db0dDUT2Ag2vltQ</recordid><startdate>20200101</startdate><enddate>20200101</enddate><creator>Taira, Toshiaki</creator><creator>Ishizaki, Yuki</creator><creator>Sakai, Kenichi</creator><creator>Sakai, Hideki</creator><creator>Imura, Tomohiro</creator><general>Japan Oil Chemists' Society</general><general>Japan Science and Technology Agency</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope></search><sort><creationdate>20200101</creationdate><title>Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction</title><author>Taira, Toshiaki ; Ishizaki, Yuki ; Sakai, Kenichi ; Sakai, Hideki ; Imura, Tomohiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c565t-98bf4effc27b96057857c9c08282d3c3416216c3e2c6d4c937193363e3eff5683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acids</topic><topic>bolaamphiphile</topic><topic>Chemical synthesis</topic><topic>Diameters</topic><topic>Metathesis</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>phosphonic acid</topic><topic>Phosphonic acids</topic><topic>Photon correlation spectroscopy</topic><topic>self-assembly</topic><topic>surface activity</topic><topic>Surface tension</topic><toplevel>online_resources</toplevel><creatorcontrib>Taira, Toshiaki</creatorcontrib><creatorcontrib>Ishizaki, Yuki</creatorcontrib><creatorcontrib>Sakai, Kenichi</creatorcontrib><creatorcontrib>Sakai, Hideki</creatorcontrib><creatorcontrib>Imura, Tomohiro</creatorcontrib><creatorcontrib>Faculty of Science and Technology</creatorcontrib><creatorcontrib>Tokyo University of Science</creatorcontrib><creatorcontrib>National Institute of Advanced Industrial Science and Technology (AIST</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><jtitle>Journal of Oleo Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taira, Toshiaki</au><au>Ishizaki, Yuki</au><au>Sakai, Kenichi</au><au>Sakai, Hideki</au><au>Imura, Tomohiro</au><aucorp>Faculty of Science and Technology</aucorp><aucorp>Tokyo University of Science</aucorp><aucorp>National Institute of Advanced Industrial Science and Technology (AIST</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction</atitle><jtitle>Journal of Oleo Science</jtitle><date>2020-01-01</date><risdate>2020</risdate><volume>69</volume><issue>11</issue><spage>1437</spage><epage>1443</epage><pages>1437-1443</pages><issn>1345-8957</issn><eissn>1347-3352</eissn><abstract>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 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 at the air/water interface (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 diameter of 81.8±27.0 nm.</abstract><cop>Tokyo</cop><pub>Japan Oil Chemists' Society</pub><doi>10.5650/jos.ess20106</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acids bolaamphiphile Chemical synthesis Diameters Metathesis NMR Nuclear magnetic resonance phosphonic acid Phosphonic acids Photon correlation spectroscopy self-assembly surface activity Surface tension |
| title | Synthesis of a Bolaamphiphilic Alkenyl Phosphonic Acid by Ru-catalyzed Olefin Cross Metathesis Reaction |
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