Cyclosiloxane polymer bearing dynamic boronic acid: Synthesis and bottom-up nanocoating

Soyeon Kim; Huie Zhu; Ali Demirci; Shunsuke Yamamoto; Tokuji Miyashita; Masaya Mitsuishi

doi:10.1039/c9py00855a

Cyclosiloxane polymer bearing dynamic boronic acid: Synthesis and bottom-up nanocoating

Soyeon Kim, Huie Zhu, Ali Demirci, Shunsuke Yamamoto, Tokuji Miyashita, Masaya Mitsuishi

ENG - Applied Chemistry

Tohoku University

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

11 Citations (Scopus)

Abstract

The paper describes facile synthesis of boronic ester-containing polycyclosiloxane (pCS-ABPE) through a one-pot-two-step hydrosilylation reaction that allows control of the functionalization efficiency stoichiometrically from zero to 100%. The combination of cyclosiloxane and boronic acid groups is expected to benefit from excellent thermal properties, flexible polymer backbone, and chemical resistance of the polycyclosiloxane part and the dynamic chemical properties of the boronic acid part to generate novel and functional hybrid polymers. Results showed that the hydrolysis of pCS-ABPE gave rise to a boronic-acid-containing polycylcosiloxane (pCS-AB) with good self-assembly nanofilm formation (6 nm film thickness) on plastic substrates through dip-coating method, mainly because of its low surface free energy (∼20 mN m^-1). In addition, the dynaminc characteristics of boronic acid groups in the pCS-AB film were demonstrated through water soluble dye Alizarin Red S (ARS) coating. The film surface underwent reversible coating through the boronic acid equilibrium: Formation of the dynamic covalent bonding (pCS-AB-ARS) and bond deformation with Zn ions for ARS-Zn complex formation. The performance makes the self-assembly nanofilm promising for chemical sensor applications.

Original language	English
Pages (from-to)	5228-5235
Number of pages	8
Journal	Polymer Chemistry
Volume	10
Issue number	38
DOIs	https://doi.org/10.1039/c9py00855a
Publication status	Published - 2019 Oct 14

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10.1039/c9py00855a

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@article{1463d697ee8345e794a48b9dc95be7a9,

title = "Cyclosiloxane polymer bearing dynamic boronic acid: Synthesis and bottom-up nanocoating",

abstract = "The paper describes facile synthesis of boronic ester-containing polycyclosiloxane (pCS-ABPE) through a one-pot-two-step hydrosilylation reaction that allows control of the functionalization efficiency stoichiometrically from zero to 100%. The combination of cyclosiloxane and boronic acid groups is expected to benefit from excellent thermal properties, flexible polymer backbone, and chemical resistance of the polycyclosiloxane part and the dynamic chemical properties of the boronic acid part to generate novel and functional hybrid polymers. Results showed that the hydrolysis of pCS-ABPE gave rise to a boronic-acid-containing polycylcosiloxane (pCS-AB) with good self-assembly nanofilm formation (6 nm film thickness) on plastic substrates through dip-coating method, mainly because of its low surface free energy (∼20 mN m-1). In addition, the dynaminc characteristics of boronic acid groups in the pCS-AB film were demonstrated through water soluble dye Alizarin Red S (ARS) coating. The film surface underwent reversible coating through the boronic acid equilibrium: Formation of the dynamic covalent bonding (pCS-AB-ARS) and bond deformation with Zn ions for ARS-Zn complex formation. The performance makes the self-assembly nanofilm promising for chemical sensor applications.",

author = "Soyeon Kim and Huie Zhu and Ali Demirci and Shunsuke Yamamoto and Tokuji Miyashita and Masaya Mitsuishi",

note = "Funding Information: The work was supported by a grant-in-aid for Scientific Research (B) (16H04197) from the Japan Society for the Promotion of Science (JSPS). The work was also supported by the Research Program of “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” in “Network Joint Research Center for Materials and Devices”. H. Zhu appreciates financial support from Morinomiyako Project for Empowering Women in Research, Tohoku University Center for Gender Equality Promotion (TUMUG). M. Mitsuishi thanks The Ogasawara Foundation for the Promotion of Science & Engineering for financial support. Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

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day = "14",

doi = "10.1039/c9py00855a",

language = "English",

volume = "10",

pages = "5228--5235",

journal = "Polymer Chemistry",

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TY - JOUR

T1 - Cyclosiloxane polymer bearing dynamic boronic acid

T2 - Synthesis and bottom-up nanocoating

AU - Kim, Soyeon

AU - Zhu, Huie

AU - Demirci, Ali

AU - Yamamoto, Shunsuke

AU - Miyashita, Tokuji

AU - Mitsuishi, Masaya

N1 - Funding Information: The work was supported by a grant-in-aid for Scientific Research (B) (16H04197) from the Japan Society for the Promotion of Science (JSPS). The work was also supported by the Research Program of “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” in “Network Joint Research Center for Materials and Devices”. H. Zhu appreciates financial support from Morinomiyako Project for Empowering Women in Research, Tohoku University Center for Gender Equality Promotion (TUMUG). M. Mitsuishi thanks The Ogasawara Foundation for the Promotion of Science & Engineering for financial support. Publisher Copyright: © 2019 The Royal Society of Chemistry.

PY - 2019/10/14

Y1 - 2019/10/14

N2 - The paper describes facile synthesis of boronic ester-containing polycyclosiloxane (pCS-ABPE) through a one-pot-two-step hydrosilylation reaction that allows control of the functionalization efficiency stoichiometrically from zero to 100%. The combination of cyclosiloxane and boronic acid groups is expected to benefit from excellent thermal properties, flexible polymer backbone, and chemical resistance of the polycyclosiloxane part and the dynamic chemical properties of the boronic acid part to generate novel and functional hybrid polymers. Results showed that the hydrolysis of pCS-ABPE gave rise to a boronic-acid-containing polycylcosiloxane (pCS-AB) with good self-assembly nanofilm formation (6 nm film thickness) on plastic substrates through dip-coating method, mainly because of its low surface free energy (∼20 mN m-1). In addition, the dynaminc characteristics of boronic acid groups in the pCS-AB film were demonstrated through water soluble dye Alizarin Red S (ARS) coating. The film surface underwent reversible coating through the boronic acid equilibrium: Formation of the dynamic covalent bonding (pCS-AB-ARS) and bond deformation with Zn ions for ARS-Zn complex formation. The performance makes the self-assembly nanofilm promising for chemical sensor applications.

AB - The paper describes facile synthesis of boronic ester-containing polycyclosiloxane (pCS-ABPE) through a one-pot-two-step hydrosilylation reaction that allows control of the functionalization efficiency stoichiometrically from zero to 100%. The combination of cyclosiloxane and boronic acid groups is expected to benefit from excellent thermal properties, flexible polymer backbone, and chemical resistance of the polycyclosiloxane part and the dynamic chemical properties of the boronic acid part to generate novel and functional hybrid polymers. Results showed that the hydrolysis of pCS-ABPE gave rise to a boronic-acid-containing polycylcosiloxane (pCS-AB) with good self-assembly nanofilm formation (6 nm film thickness) on plastic substrates through dip-coating method, mainly because of its low surface free energy (∼20 mN m-1). In addition, the dynaminc characteristics of boronic acid groups in the pCS-AB film were demonstrated through water soluble dye Alizarin Red S (ARS) coating. The film surface underwent reversible coating through the boronic acid equilibrium: Formation of the dynamic covalent bonding (pCS-AB-ARS) and bond deformation with Zn ions for ARS-Zn complex formation. The performance makes the self-assembly nanofilm promising for chemical sensor applications.

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U2 - 10.1039/c9py00855a

DO - 10.1039/c9py00855a

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SN - 1759-9954

VL - 10

SP - 5228

EP - 5235

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 38

ER -

Cyclosiloxane polymer bearing dynamic boronic acid: Synthesis and bottom-up nanocoating

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