Synthesis and guest-binding study of polytopic multi(cyclophane) hosts

Osamu Hayashida; Yousuke Takaoka; Itaru Hamachi

doi:10.1016/j.tetlet.2005.07.010

Synthesis and guest-binding study of polytopic multi(cyclophane) hosts

Osamu Hayashida, Yousuke Takaoka, Itaru Hamachi

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Novel bis(cyclophanes) bearing glucosides and pentakis(cyclophanes) bearing glucosides were prepared as water-soluble hosts by connecting two or five macrocyclic skeletons, respectively. The guest-binding affinities of the present bis(cyclophanes) and pentakis(cyclophanes) toward a hydrophobic dye, 6-p-toluidinonaphthalene-2-sulfonate, were enhanced 13- and 1200-fold, respectively, relative to that by a corresponding monocyclic cyclophane, reflecting multivalency effects in macrocycles.

Original language	English
Pages (from-to)	6589-6592
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2005.07.010
Publication status	Published - 2005 Sept 19

Keywords

Cluster effect
Complexation
Multivalency
Water-soluble cyclophane

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10.1016/j.tetlet.2005.07.010

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title = "Synthesis and guest-binding study of polytopic multi(cyclophane) hosts",

abstract = "Novel bis(cyclophanes) bearing glucosides and pentakis(cyclophanes) bearing glucosides were prepared as water-soluble hosts by connecting two or five macrocyclic skeletons, respectively. The guest-binding affinities of the present bis(cyclophanes) and pentakis(cyclophanes) toward a hydrophobic dye, 6-p-toluidinonaphthalene-2-sulfonate, were enhanced 13- and 1200-fold, respectively, relative to that by a corresponding monocyclic cyclophane, reflecting multivalency effects in macrocycles.",

keywords = "Cluster effect, Complexation, Multivalency, Water-soluble cyclophane",

author = "Osamu Hayashida and Yousuke Takaoka and Itaru Hamachi",

note = "Funding Information: This is partially supported by Izumi Science and Technology Foundation. ",

year = "2005",

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doi = "10.1016/j.tetlet.2005.07.010",

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T1 - Synthesis and guest-binding study of polytopic multi(cyclophane) hosts

AU - Hayashida, Osamu

AU - Takaoka, Yousuke

AU - Hamachi, Itaru

N1 - Funding Information: This is partially supported by Izumi Science and Technology Foundation.

PY - 2005/9/19

Y1 - 2005/9/19

N2 - Novel bis(cyclophanes) bearing glucosides and pentakis(cyclophanes) bearing glucosides were prepared as water-soluble hosts by connecting two or five macrocyclic skeletons, respectively. The guest-binding affinities of the present bis(cyclophanes) and pentakis(cyclophanes) toward a hydrophobic dye, 6-p-toluidinonaphthalene-2-sulfonate, were enhanced 13- and 1200-fold, respectively, relative to that by a corresponding monocyclic cyclophane, reflecting multivalency effects in macrocycles.

AB - Novel bis(cyclophanes) bearing glucosides and pentakis(cyclophanes) bearing glucosides were prepared as water-soluble hosts by connecting two or five macrocyclic skeletons, respectively. The guest-binding affinities of the present bis(cyclophanes) and pentakis(cyclophanes) toward a hydrophobic dye, 6-p-toluidinonaphthalene-2-sulfonate, were enhanced 13- and 1200-fold, respectively, relative to that by a corresponding monocyclic cyclophane, reflecting multivalency effects in macrocycles.

KW - Cluster effect

KW - Complexation

KW - Multivalency

KW - Water-soluble cyclophane

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U2 - 10.1016/j.tetlet.2005.07.010

DO - 10.1016/j.tetlet.2005.07.010

M3 - Article

AN - SCOPUS:23844533718

SN - 0040-4039

VL - 46

SP - 6589

EP - 6592

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Synthesis and guest-binding study of polytopic multi(cyclophane) hosts

Abstract

Keywords

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