| 侧链带有L-氨基酸乙酯的螺旋聚苯乙炔衍生物的手性识别能力研究 |
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| 引用本文： | 张春红,王海伦,刘方彬,沈贤德,刘立佳,堺井亮介,佐藤敏文,覚知豊次,岡本佳男.侧链带有L-氨基酸乙酯的螺旋聚苯乙炔衍生物的手性识别能力研究[J].高分子学报,2013(6):811-816. |
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| 作者姓名： | 张春红 王海伦 刘方彬 沈贤德 刘立佳 堺井亮介 佐藤敏文 覚知豊次 岡本佳男 |
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| 作者单位： | 哈尔滨工程大学材料科学与化学工程学院高分子材料研究中心;哈尔滨工程大学超轻材料与表面技术教育部重点实验室;日本旭川工业高等专门学校物质化学工学科;日本北海道大学工学研究院;日本名古屋大学 |
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| 基金项目： | 中央高校基本科研业务费专项资金(项目号HEUCFT1009,HEUCF20131009,HEUCF201310003,HEUCFR1227);教育部留学回国人员科研启动金(项目号20111568);黑龙江省自然科学基金(基金号B201013);哈尔滨市科技创新人才研究专项资金(项目号2012RFLXG001)资助项目 |
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| 摘 要： | 采用Rh(nbd)BPh4催化剂合成了3种侧链带有L-氨基酸乙酯的螺旋聚苯乙炔衍生物PPA-S-Phe、PPA-S-Leu和PPA-A-Leu,并将其涂覆在氨丙基硅胶上制备高效液相色谱(HPLC)手性固定相(CSP),研究其对7种对映体的手性识别能力.由于侧链手性基团或主链与手性基团之间的链接基团不同,PPA-S-Phe、PPA-S-Leu和PPA-A-Leu形成了不同的螺旋构象,并表现出对对映体不同的手性识别能力.PPA-S-Phe和PPA-S-Leu的主链与手性基团之间的链接基团均为磺酰胺基,侧链手性基团为L-亮氨酸乙酯的PPA-S-Leu的手性识别能力优于侧链手性基团为L-苯丙氨酸乙酯的PPA-S-Phe.PPA-S-Leu和PPA-A-Leu的侧链手性基团均为L-亮氨酸乙酯,以酰胺基为链接基团的PPA-A-Leu的手性识别能力明显优于以磺酰胺基为链接基团的PPA-S-Leu.螺旋聚苯乙炔主链与侧链手性基团之间的链接基团、侧链手性基团在手性识别中均发挥十分着重要作用.
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| 关 键 词： | 聚苯乙炔衍生物 螺旋构象 手性侧链 链接基团 高效液相色谱 手性识别 |
CHIRAL RECOGNITION OF HELICAL POLY (PHENYLACETYLENE) DERIVATIVES BEARING L-AMINO ACID ETHYL ESTER PENDANTS |
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| Institution: | Chun-hong Zhang1,2,Hai-lun Wang1,Fang-bin Liu1,Xian-de Shen1,Li-jia Liu1, Ryosuke Sakai3,Toshifumi Satoh4,Toyoji Kakuchi4,Yoshio Okamoto5(1 Polymer Materials Research Center,College of Materials Science and Chemical Engineering, Harbin Engineering University,Harbin 150001)(2 Key Laboratory of Superlight Materials and Surface Technology,Ministry of Education, Harbin Engineering University,Harbin 150001)(3 Department of Materials Chemistry,Asahikawa National College of Technology,Asahikawa 071-8142,Japan)(4 Graduate School of Engineering,Hokkaido University,Sapporo 060-8628,Japan)(5 Nagoya University,Nagoya 464-8603,Japan) |
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| Abstract: | Three one-handed helical poly(phenylacetylene) derivatives bearing L-amino acid ethyl ester pendants,PPA-S-Phe,PPA-S-Leu and PPA-A-Leu were respectively synthesized by the polymerization of the corresponding monomers using Rh(nbd)BPh4 as a catalyst,and their chiral recognition abilities for seven racemates were evaluated as chiral stationary phases(CSPs) for high-performance liquid chromatography(HPLC) after coating them on silica gel.The difference between PPA-S-Phe and PPA-S-Leu is the chiral pendants.The chiral pendant of PPA-S-Phe is L-phenylalanine ethyl ester,while that of PPA-S-Leu is L-leucine ethyl ester.The difference between PPA-S-Leu and PPA-A-Leu is the linkage groups between polymer main chains and chiral pendants.The linkage of PPA-S-Leu is sulphonamide group,while that of PPA-A-Leu is amide group.PPA-S-Phe,PPA-S-Leu and PPA-A-Leu possess their characteristic helical conformation and show their characteristic chiral recognition depending on the chiral pendants and the linkage groups.When linkage is a sulphonamide group,PPA-S-Leu with L-leucine ethyl ester pendants shows higher chiral recognition abilities than PPA-S-Phe with L-phenylalanine ethyl ester pendants.When chiral pendant is L-leucine ethyl ester,PPA-A-Leu with amide linkage shows higher chiral recognition abilities than PPA-S-Leu with sulphonamide linkage.It is concluded that the linkage groups play an important role in chiral recognition as well as the chiral pendants. |
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| Keywords: | Poly(phenylacetylene) derivatives Helical conformation Chiral pendants Linkage group High-performance liquid chromatography(HPLC) Chiral recognition |
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