Accumulation of phenyl boronic acid-carrying telomers on a gold surface

Hiromi Kitano; Shinta Morokoshi; Kazuhiko Ohhori; Makoto Gemmei-Ide; Yoshiyuki Yokoyama; Kohji Ohno

doi:10.1016/j.jcis.2004.01.027

Accumulation of phenyl boronic acid-carrying telomers on a gold surface

Hiromi Kitano^*, Shinta Morokoshi, Kazuhiko Ohhori, Makoto Gemmei-Ide, Yoshiyuki Yokoyama, Kohji Ohno

^*Corresponding author for this work

Applied Chemistry

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

14 Scopus citations

Abstract

By coupling two equivalents of N,N-diethyldithiocarbamoylmethylbenzoic acid succinimidyl ester with cystamine dihydrochloride, a disulfide-carrying compound (Cys-BDC) was prepared and used as iniferter (a compound which pursues initiation, chain transfer, and termination) in the telomerization of N,N-dimethylacrylamide and 3-acrylamidophenylboronic acid. The telomerization was carried out in the presence of N,N,N′,N′-tetraethylthiuram disulfide under photoirradiation at 365 nm. An aqueous solution of the telomer obtained showed responsiveness to both temperature and sugars as confirmed by the turbidity measurements. The telomer formed a self-assembled monolayer (SAM) on a gold surface as confirmed by both cyclic voltammetry (CV) and ellipsometry. The recognition of sugar residues by the telomer SAM constructed on the gold electrode was detected by the CV measurements. The usefulness of the iniferter to prepare various telomer-carrying SAMs with bio-related functions was strongly suggested.

Original language	English
Pages (from-to)	106-114
Number of pages	9
Journal	Journal of Colloid and Interface Science
Volume	273
Issue number	1
DOIs	https://doi.org/10.1016/j.jcis.2004.01.027
State	Published - 2004/05/01

Keywords

Iniferter
Phenylboronic acid
Self-assembled monolayer
Sugar protein
Telomerization
Temperature responsiveness

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Biomaterials
Surfaces, Coatings and Films
Colloid and Surface Chemistry

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10.1016/j.jcis.2004.01.027

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@article{1bea9e3c13ef453fb5ac6c6a1f6e085f,

title = "Accumulation of phenyl boronic acid-carrying telomers on a gold surface",

abstract = "By coupling two equivalents of N,N-diethyldithiocarbamoylmethylbenzoic acid succinimidyl ester with cystamine dihydrochloride, a disulfide-carrying compound (Cys-BDC) was prepared and used as iniferter (a compound which pursues initiation, chain transfer, and termination) in the telomerization of N,N-dimethylacrylamide and 3-acrylamidophenylboronic acid. The telomerization was carried out in the presence of N,N,N′,N′-tetraethylthiuram disulfide under photoirradiation at 365 nm. An aqueous solution of the telomer obtained showed responsiveness to both temperature and sugars as confirmed by the turbidity measurements. The telomer formed a self-assembled monolayer (SAM) on a gold surface as confirmed by both cyclic voltammetry (CV) and ellipsometry. The recognition of sugar residues by the telomer SAM constructed on the gold electrode was detected by the CV measurements. The usefulness of the iniferter to prepare various telomer-carrying SAMs with bio-related functions was strongly suggested.",

keywords = "Iniferter, Phenylboronic acid, Self-assembled monolayer, Sugar protein, Telomerization, Temperature responsiveness",

author = "Hiromi Kitano and Shinta Morokoshi and Kazuhiko Ohhori and Makoto Gemmei-Ide and Yoshiyuki Yokoyama and Kohji Ohno",

note = "Funding Information: This work was supported by Grants-in-Aid for Scientific Research (12450381, 13022225, and 13555260) from the Ministry of Education, Science, and Culture. The authors sincerely thank Professor T. Fukuda, Institute for Chemical Research, Kyoto University, for allowing us to use the ellipsometric apparatus. The authors are also graceful to Dr. J.C. Norrild, University of Copenhagen, for the kind suggestion concerning the sugar recognition by boronic acid.",

year = "2004",

month = may,

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doi = "10.1016/j.jcis.2004.01.027",

language = "英語",

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pages = "106--114",

journal = "Journal of Colloid and Interface Science",

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TY - JOUR

T1 - Accumulation of phenyl boronic acid-carrying telomers on a gold surface

AU - Kitano, Hiromi

AU - Morokoshi, Shinta

AU - Ohhori, Kazuhiko

AU - Gemmei-Ide, Makoto

AU - Yokoyama, Yoshiyuki

AU - Ohno, Kohji

N1 - Funding Information: This work was supported by Grants-in-Aid for Scientific Research (12450381, 13022225, and 13555260) from the Ministry of Education, Science, and Culture. The authors sincerely thank Professor T. Fukuda, Institute for Chemical Research, Kyoto University, for allowing us to use the ellipsometric apparatus. The authors are also graceful to Dr. J.C. Norrild, University of Copenhagen, for the kind suggestion concerning the sugar recognition by boronic acid.

PY - 2004/5/1

Y1 - 2004/5/1

N2 - By coupling two equivalents of N,N-diethyldithiocarbamoylmethylbenzoic acid succinimidyl ester with cystamine dihydrochloride, a disulfide-carrying compound (Cys-BDC) was prepared and used as iniferter (a compound which pursues initiation, chain transfer, and termination) in the telomerization of N,N-dimethylacrylamide and 3-acrylamidophenylboronic acid. The telomerization was carried out in the presence of N,N,N′,N′-tetraethylthiuram disulfide under photoirradiation at 365 nm. An aqueous solution of the telomer obtained showed responsiveness to both temperature and sugars as confirmed by the turbidity measurements. The telomer formed a self-assembled monolayer (SAM) on a gold surface as confirmed by both cyclic voltammetry (CV) and ellipsometry. The recognition of sugar residues by the telomer SAM constructed on the gold electrode was detected by the CV measurements. The usefulness of the iniferter to prepare various telomer-carrying SAMs with bio-related functions was strongly suggested.

AB - By coupling two equivalents of N,N-diethyldithiocarbamoylmethylbenzoic acid succinimidyl ester with cystamine dihydrochloride, a disulfide-carrying compound (Cys-BDC) was prepared and used as iniferter (a compound which pursues initiation, chain transfer, and termination) in the telomerization of N,N-dimethylacrylamide and 3-acrylamidophenylboronic acid. The telomerization was carried out in the presence of N,N,N′,N′-tetraethylthiuram disulfide under photoirradiation at 365 nm. An aqueous solution of the telomer obtained showed responsiveness to both temperature and sugars as confirmed by the turbidity measurements. The telomer formed a self-assembled monolayer (SAM) on a gold surface as confirmed by both cyclic voltammetry (CV) and ellipsometry. The recognition of sugar residues by the telomer SAM constructed on the gold electrode was detected by the CV measurements. The usefulness of the iniferter to prepare various telomer-carrying SAMs with bio-related functions was strongly suggested.

KW - Iniferter

KW - Phenylboronic acid

KW - Self-assembled monolayer

KW - Sugar protein

KW - Telomerization

KW - Temperature responsiveness

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U2 - 10.1016/j.jcis.2004.01.027

DO - 10.1016/j.jcis.2004.01.027

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SN - 0021-9797

VL - 273

SP - 106

EP - 114

JO - Journal of Colloid and Interface Science

JF - Journal of Colloid and Interface Science

IS - 1

ER -

Accumulation of phenyl boronic acid-carrying telomers on a gold surface

Abstract

Keywords

ASJC Scopus subject areas

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