Helicity induction on a poly(phenylacetylene) derivative bearing Aza-15-crown-5 ether pendants in organic solvents and water

被引：62

作者：

Nonokawa, R ^{[1
]}

Oobo, M ^{[1
]}

Yashima, E ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

MACROMOLECULES | 2003年 / 36卷 / 17期

关键词：

D O I：

10.1021/ma034547k

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

A novel stereoregular poly(phenylacetylene) with the bulky aza-15-crown-5 ether as the pendant was prepared by polymerization of the corresponding phenylacetylene monomer with a rhodium catalyst. The polymer was found to form a predominantly one-handed helical conformation upon complexation with various chiral compounds, such as amino acids, amines, and amino alcohols through noncovalent interaction in organic solvents and water. The complexes exhibited an induced circular dichroism (ICD) in the UV-vis region of the polymer backbone; in particular, the polymer showed high affinity to secondary amines, and the complexes exhibited relatively intense ICDs. The assay of 19 common free L-amino acids gave the same ICD sign in acetonitrile-5 N HClO4 (99.88/0.12, v/v). The effects of pH, temperature, and guest concentration on the ICD during the complexation of poly-1 with chiral compounds were also investigated.

引用

页码：6599 / 6606

页数：8

共 89 条

[61] Synthesis beyond the molecule [J].

Reinhoudt, DN ;

Crego-Calama, M .

SCIENCE, 2002, 295 (5564) :2403-2407

[62]

Rüdiger V, 1999, EUR J ORG CHEM, V1999, P1847

[63] Synthesis and macromolecular helicity induction of a stereoregular polyacetylene bearing a carboxy group with natural amino acids in water [J].

Saito, MA ;

Maeda, K ;

Onouchi, H ;

Yashima, E .

MACROMOLECULES, 2000, 33 (13) :4616-4618

[64] Trapped kinetic states, chiral amplification and molecular chaperoning in synthetic polymers: Chiral induction in polyguanidines through ion pair interactions [J].

Schlitzer, DS ;

Novak, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :2196-2197

[65] Positive allosteric systems designed on dynamic supramolecular scaffolds: Toward switching and amplification of guest affinity and selectivity [J].

Shinkai, S ;

Ikeda, M ;

Sugasaki, A ;

Takeuchi, M .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) :494-503

[66]

Simionescu C. I., 1982, Prog. Polym. Sci, V8, P133, DOI [10.1016/0079-6700(82)90009-0, DOI 10.1016/0079-6700(82)90009-0]

[67] POLYMERIZATION OF ACETYLENIC DERIVATIVES .30. ISOMERS OF POLYPHENYLACETYLENE [J].

SIMIONESCU, CI ;

PERCEC, V ;

DUMITRESCU, S .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1977, 15 (10) :2497-2509

[68]

Sirish M, 2002, CHEM-EUR J, V8, P1181, DOI 10.1002/1521-3765(20020301)8:5<1181::AID-CHEM1181>3.0.CO

[69]

2-U

[70] HOST-GUEST COMPLEXATION .14. HOST COVALENTLY BOUND TO POLYSTYRENE RESIN FOR CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERS OF AMINO-ACID AND ESTER SALTS [J].

SOGAH, GDY ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (11) :3035-3042

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