Chiral supramolecular polymers formed by host-guest interactions

被引：181

作者：

Miyauchi, M ^{[1
]}

Takashima, Y ^{[1
]}

Yamaguchi, H ^{[1
]}

Harada, A ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Macromol Sci, Toyonaka, Osaka 5600043, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 09期

关键词：

D O I：

10.1021/ja043289j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Cyclodextrin with a p-t-butoxyaminocinnamoylamino group in the 3-position (3-p-(t)BocCiNHa-alphaCD) has been found to form a supramolecular polymer in an aqueous solution. The degree of polymerization of the supramolecular polymer is higher than 15 at 20 mM, as proved by VPO (vapor pressure osmometry) measurements and turbo ion spray TOF MS measurements. The existence of substitution/ substitution interactions between adjacent monomers of the supramolecular polymer have been confirmed by the observation of positive and negative Cotton bands in circular dichroism spectra. The mechanism for the induction of the chirality was confirmed using model compounds. The substituents were found to exist as a left-handed anti configuration in supramolecular polymers. The supramolecular polymer was found to take a helical structure. The structure of the supramolecular polymer was observed by STM measurements.

引用

页码：2984 / 2989

页数：6

共 42 条

[1]

Berova N., 2000, Circular Dichroism: Principles and Applications

[2] Polymer bilayer formation due to specific interactions between β-cyclodextrin and adamantane:: A surface force study [J].

Blomberg, E ;

Kumpulainen, A ;

David, C ;

Amiel, C .

LANGMUIR, 2004, 20 (24) :10449-10454

[3] Supramolecular polymers [J].

Brunsveld, L ;

Folmer, BJB ;

Meijer, EW ;

Sijbesma, RP .

CHEMICAL REVIEWS, 2001, 101 (12) :4071-4097

[4] Interconnective host-guest complexation of β-cyclodextrin-calix[4]arene couples [J].

Bügler, J ;

Sommerdijk, NAJM ;

Visser, AJWG ;

van Hoek, A ;

Nolte, RJM ;

Engbersen, JFJ ;

Reinhoudt, DN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :28-33

[5]

Ciferri A, 2000, SUPRAMOLECULAR POLYMERS, P1

[6] A modified cyclodextrin with a fully encapsulated dansyl group: Self-inclusion in the solid state and in solution [J].

Corradini, R ;

Dossena, A ;

Marchelli, R ;

Panagia, A ;

Sartor, G ;

Saviano, M ;

Lombardi, A ;

Pavone, V .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (04) :373-381

[7] Fluorescent chemosensor for organic guests and copper(II) ion based on dansyldiethylenetriamine-modified beta-cyclodextrin [J].

Corradini, R ;

Dossena, A ;

Galaverna, G ;

Marchelli, R ;

Panagia, A ;

Sartor, G .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6283-6289

[8] ELECTRON-MICROSCOPIC STUDY OF SUPRAMOLECULAR LIQUID-CRYSTALLINE POLYMERS FORMED BY MOLECULAR-RECOGNITION-DIRECTED SELF-ASSEMBLY FROM COMPLEMENTARY CHIRAL COMPONENTS [J].

GULIKKRZYWICKI, T ;

FOUQUEY, C ;

LEHN, JM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :163-167

[9] FLUORESCENT SENSORS OF MOLECULAR RECOGNITION - MODIFIED CYCLODEXTRINS CAPABLE OF EXHIBITING GUEST-RESPONSIVE TWISTED INTRAMOLECULAR CHARGE-TRANSFER FLUORESCENCE [J].

HAMASAKI, K ;

IKEDA, H ;

NAKAMURA, A ;

UENO, A ;

TODA, F ;

SUZUKI, I ;

OSA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5035-5040

[10] Supramolecular polymers formed by cinnamoyl cyclodextrins [J].

Harada, A ;

Miyauchi, M ;

Hoshino, T .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2003, 41 (22) :3519-3523

← 1 2 3 4 5 →