Synthesis and chiroptical properties of a helical poly(phenylacetylene) bearing optically active pyrene pendants

被引：22

作者：

Lin, Hongzhen ^{[1
]}

Morino, Kazuhide ^{[1
]}

Yashima, Eiji ^{[1
]}

机构：

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

来源：

CHIRALITY | 2008年 / 20卷 / 3-4期

关键词：

helix; chirality; circular dichroism; fluorescence; polyacetylenes;

D O I：

10.1002/chir.20457

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

A novel poly (phenylacetylene) derivative bearing optically active pyrene moieties as the pendant groups (poly-(R)-1) was prepared by the polymerization of the corresponding monomer (R)-1 in the presence of a rhodium catalyst, and its chiroptical property was investigated. Poly-(R)-1 exhibited an induced circular dichroism (ICD) in the polymer backbone region due to the predominantly one-handed helical conformation. The ICD pattern dramatically changed and was accompanied by inversion of the Cotton effect sign in response to a change in the temperature and solvent, indicating that poly-(R)-1 underwent a helix-helix transition in response to the external stimuli.

引用

页码：386 / 392

页数：7

共 49 条

[1]

FACILE SYNTHESIS OF ETHYNYLATED BENZOIC-ACID DERIVATIVES AND AROMATIC-COMPOUNDS VIA ETHYNYLTRIMETHYLSILANE [J].

AUSTIN, WB ;

BILOW, N ;

KELLEGHAN, WJ ;

LAU, KSY .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2280-2286

[2]

Cheon KS, 2000, ANGEW CHEM INT EDIT, V39, P1482, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1482::AID-ANIE1482>3.0.CO

[3]

2-7

[4]

Syntheses, hydrogen-bonding interactions, tunable chain helicities, and cooperative supramolecular associations and dissociations of poly(phenylacetylene)s bearing L-valine pendants: Toward the development of proteomimetic polyenes [J].

Cheuk, KKL ;

Lam, JWY ;

Lai, LM ;

Dong, YP ;

Tang, BZ .

MACROMOLECULES, 2003, 36 (26) :9752-9762

[5]

Amino acid-containing polyacetylenes: Synthesis, hydrogen bonding, chirality transcription, and chain helicity of amphiphilic poly(phenylacetylene)s carrying L-leucine pendants [J].

Cheuk, KKL ;

Lam, JWY ;

Chen, JW ;

Lai, LM ;

Tang, BZ .

MACROMOLECULES, 2003, 36 (16) :5947-5959

[6]

Chiral architectures from macromolecular building blocks [J].

Cornelissen, JJLM ;

Rowan, AE ;

Nolte, RJM ;

Sommerdijk, NAJM .

CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070

[7]

Optically active polysilanes. Ten years of progress and new polymer twist for nanoscience and nanotechnology [J].

Fujiki, M ;

Koe, JR ;

Terao, K ;

Sato, T ;

Teramoto, A ;

Watanabe, J .

POLYMER JOURNAL, 2003, 35 (04) :297-344

[8]

Fujiki M, 2001, MACROMOL RAPID COMM, V22, P539, DOI 10.1002/1521-3927(20010501)22:8<539::AID-MARC539>3.0.CO

[9]

2-K

[10]

Helix magic. Thermo-driven chiroptical switching and screw-sense inversion of flexible rod helical polysilylenes [J].

Fujiki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3336-3343

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