Photo-tunable morphologies of β-cyclodextrin-threaded inclusion complexes containing a terminal cholesteryl group

Wen Tzu Liu; Norimitsu Tohnai; Ichiro Hisaki; Mikiji Miyata; Dolok Steven; Yi Hong Chiu; Jui Hsiang Liu

doi:10.1166/sam.2012.1389

Photo-tunable morphologies of β-cyclodextrin-threaded inclusion complexes containing a terminal cholesteryl group

Wen Tzu Liu
, Norimitsu Tohnai
, Ichiro Hisaki
, Mikiji Miyata
, Dolok Steven
, Yi Hong Chiu
, Jui Hsiang Liu

Department of Chemical Engineering

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

1 Citation (Scopus)

Abstract

The threading of cyclodextrin (CD) to convert from intramolecular to intermolecular hydrogen bonding leads to the self-assembly of an inclusion complex (IC). A chiral cholesteryl-E-4-(11-acryloxy-undecaloxy)-cinnamate (CAUC) monomer containing a photoisomerizable C C bond and a cholesteryl terminal group was synthesized andthreaded with β-CD to form an inclusion complex. The synthesized IC forms a rod-like construction because of the enhanced intermolecular hydrogen bonding. After UV irradiation, the self-assembled rod structure changed to a spherical structure because of the change in the molecular polarity and intermolecular forces. The bent structure of Z-CAUC may release some of the threaded CDs and lead to a decrease in intermolecular forces. Due to a high energy barrier, the E-Z configurational photoisomerization of CAUC is irreversible.

Original language	English
Pages (from-to)	1031-1038
Number of pages	8
Journal	Science of Advanced Materials
Volume	4
Issue number	10
DOIs	https://doi.org/10.1166/sam.2012.1389
Publication status	Published - 2012 Oct

All Science Journal Classification (ASJC) codes

General Materials Science

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10.1166/sam.2012.1389

Cite this

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title = "Photo-tunable morphologies of β-cyclodextrin-threaded inclusion complexes containing a terminal cholesteryl group",

abstract = "The threading of cyclodextrin (CD) to convert from intramolecular to intermolecular hydrogen bonding leads to the self-assembly of an inclusion complex (IC). A chiral cholesteryl-E-4-(11-acryloxy-undecaloxy)-cinnamate (CAUC) monomer containing a photoisomerizable C C bond and a cholesteryl terminal group was synthesized andthreaded with β-CD to form an inclusion complex. The synthesized IC forms a rod-like construction because of the enhanced intermolecular hydrogen bonding. After UV irradiation, the self-assembled rod structure changed to a spherical structure because of the change in the molecular polarity and intermolecular forces. The bent structure of Z-CAUC may release some of the threaded CDs and lead to a decrease in intermolecular forces. Due to a high energy barrier, the E-Z configurational photoisomerization of CAUC is irreversible.",

author = "Liu, \{Wen Tzu\} and Norimitsu Tohnai and Ichiro Hisaki and Mikiji Miyata and Dolok Steven and Chiu, \{Yi Hong\} and Liu, \{Jui Hsiang\}",

year = "2012",

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AU - Liu, Wen Tzu

AU - Tohnai, Norimitsu

AU - Hisaki, Ichiro

AU - Miyata, Mikiji

AU - Steven, Dolok

AU - Chiu, Yi Hong

AU - Liu, Jui Hsiang

PY - 2012/10

Y1 - 2012/10

N2 - The threading of cyclodextrin (CD) to convert from intramolecular to intermolecular hydrogen bonding leads to the self-assembly of an inclusion complex (IC). A chiral cholesteryl-E-4-(11-acryloxy-undecaloxy)-cinnamate (CAUC) monomer containing a photoisomerizable C C bond and a cholesteryl terminal group was synthesized andthreaded with β-CD to form an inclusion complex. The synthesized IC forms a rod-like construction because of the enhanced intermolecular hydrogen bonding. After UV irradiation, the self-assembled rod structure changed to a spherical structure because of the change in the molecular polarity and intermolecular forces. The bent structure of Z-CAUC may release some of the threaded CDs and lead to a decrease in intermolecular forces. Due to a high energy barrier, the E-Z configurational photoisomerization of CAUC is irreversible.

AB - The threading of cyclodextrin (CD) to convert from intramolecular to intermolecular hydrogen bonding leads to the self-assembly of an inclusion complex (IC). A chiral cholesteryl-E-4-(11-acryloxy-undecaloxy)-cinnamate (CAUC) monomer containing a photoisomerizable C C bond and a cholesteryl terminal group was synthesized andthreaded with β-CD to form an inclusion complex. The synthesized IC forms a rod-like construction because of the enhanced intermolecular hydrogen bonding. After UV irradiation, the self-assembled rod structure changed to a spherical structure because of the change in the molecular polarity and intermolecular forces. The bent structure of Z-CAUC may release some of the threaded CDs and lead to a decrease in intermolecular forces. Due to a high energy barrier, the E-Z configurational photoisomerization of CAUC is irreversible.

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DO - 10.1166/sam.2012.1389

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JF - Science of Advanced Materials

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Photo-tunable morphologies of β-cyclodextrin-threaded inclusion complexes containing a terminal cholesteryl group

Abstract

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