Functionalization of SBA-15 mesoporous materials using "thiol-ene click" Michael addition reaction

Sushma Kumari; Bharmana Malvi; Anal Kr Ganai; Vijayamohanan K. Pillai; Sayam Sen Gupta

doi:10.1021/jp2056442

Functionalization of SBA-15 mesoporous materials using "thiol-ene click" Michael addition reaction

Sushma Kumari, Bharmana Malvi, Anal Kr Ganai, Vijayamohanan K. Pillai, Sayam Sen Gupta

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

36 Scopus citations

Abstract

Methacrylate-labeled SBA-15 has been successfully synthesized from calcined SBA-15 and commercially available 3-trichlorosilyl propylmethacrylate. This material undergoes efficient thiol-ene "click reaction" with a variety of both thiol and disulfide-containing substrates in aqueous and organic media. The products were thoroughly characterized by a variety of analytical techniques including multinuclear (¹³C, ²⁹Si) solid-state NMR, TG-DTA, and nitrogen adsorption desorption studies. Disulfide-containing substrates in which the TCEP-mediated reduction of the disulfide bond and its subsequent addition to the methacrylate group anchored in SBA-15 in one-pot were used to synthesize a silica-protein hybrid material composed of biotin-labeled SBA-15 and streptavidin. Electrochemically active material was synthesized from the reaction of ferrocene-containing thiol and the methacrylate-labeled SBA-15. The ease of synthesis for the methacrylate-labeled SBA-15 material together with its ability to undergo efficient chemoselective thiol-ene reaction would make it a very attractive platform for the development of covalently anchored enzymes and sensors.

Original language	English
Pages (from-to)	17774-17781
Number of pages	8
Journal	Journal of Physical Chemistry C
Volume	115
Issue number	36
DOIs	https://doi.org/10.1021/jp2056442
State	Published - 15 Sep 2011
Externally published	Yes

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
General Energy
Physical and Theoretical Chemistry
Surfaces, Coatings and Films

Access to Document

10.1021/jp2056442

Cite this

@article{c558976966fb47d297ab3110e1578dfa,

title = "Functionalization of SBA-15 mesoporous materials using {"}thiol-ene click{"} Michael addition reaction",

abstract = "Methacrylate-labeled SBA-15 has been successfully synthesized from calcined SBA-15 and commercially available 3-trichlorosilyl propylmethacrylate. This material undergoes efficient thiol-ene {"}click reaction{"} with a variety of both thiol and disulfide-containing substrates in aqueous and organic media. The products were thoroughly characterized by a variety of analytical techniques including multinuclear (13C, 29Si) solid-state NMR, TG-DTA, and nitrogen adsorption desorption studies. Disulfide-containing substrates in which the TCEP-mediated reduction of the disulfide bond and its subsequent addition to the methacrylate group anchored in SBA-15 in one-pot were used to synthesize a silica-protein hybrid material composed of biotin-labeled SBA-15 and streptavidin. Electrochemically active material was synthesized from the reaction of ferrocene-containing thiol and the methacrylate-labeled SBA-15. The ease of synthesis for the methacrylate-labeled SBA-15 material together with its ability to undergo efficient chemoselective thiol-ene reaction would make it a very attractive platform for the development of covalently anchored enzymes and sensors.",

author = "Sushma Kumari and Bharmana Malvi and Ganai, {Anal Kr} and Pillai, {Vijayamohanan K.} and {Sen Gupta}, Sayam",

year = "2011",

month = sep,

day = "15",

doi = "10.1021/jp2056442",

language = "English",

volume = "115",

pages = "17774--17781",

journal = "Journal of Physical Chemistry C",

issn = "1932-7447",

publisher = "American Chemical Society",

number = "36",

}

TY - JOUR

T1 - Functionalization of SBA-15 mesoporous materials using "thiol-ene click" Michael addition reaction

AU - Kumari, Sushma

AU - Malvi, Bharmana

AU - Ganai, Anal Kr

AU - Pillai, Vijayamohanan K.

AU - Sen Gupta, Sayam

PY - 2011/9/15

Y1 - 2011/9/15

N2 - Methacrylate-labeled SBA-15 has been successfully synthesized from calcined SBA-15 and commercially available 3-trichlorosilyl propylmethacrylate. This material undergoes efficient thiol-ene "click reaction" with a variety of both thiol and disulfide-containing substrates in aqueous and organic media. The products were thoroughly characterized by a variety of analytical techniques including multinuclear (13C, 29Si) solid-state NMR, TG-DTA, and nitrogen adsorption desorption studies. Disulfide-containing substrates in which the TCEP-mediated reduction of the disulfide bond and its subsequent addition to the methacrylate group anchored in SBA-15 in one-pot were used to synthesize a silica-protein hybrid material composed of biotin-labeled SBA-15 and streptavidin. Electrochemically active material was synthesized from the reaction of ferrocene-containing thiol and the methacrylate-labeled SBA-15. The ease of synthesis for the methacrylate-labeled SBA-15 material together with its ability to undergo efficient chemoselective thiol-ene reaction would make it a very attractive platform for the development of covalently anchored enzymes and sensors.

AB - Methacrylate-labeled SBA-15 has been successfully synthesized from calcined SBA-15 and commercially available 3-trichlorosilyl propylmethacrylate. This material undergoes efficient thiol-ene "click reaction" with a variety of both thiol and disulfide-containing substrates in aqueous and organic media. The products were thoroughly characterized by a variety of analytical techniques including multinuclear (13C, 29Si) solid-state NMR, TG-DTA, and nitrogen adsorption desorption studies. Disulfide-containing substrates in which the TCEP-mediated reduction of the disulfide bond and its subsequent addition to the methacrylate group anchored in SBA-15 in one-pot were used to synthesize a silica-protein hybrid material composed of biotin-labeled SBA-15 and streptavidin. Electrochemically active material was synthesized from the reaction of ferrocene-containing thiol and the methacrylate-labeled SBA-15. The ease of synthesis for the methacrylate-labeled SBA-15 material together with its ability to undergo efficient chemoselective thiol-ene reaction would make it a very attractive platform for the development of covalently anchored enzymes and sensors.

UR - http://www.scopus.com/inward/record.url?scp=80052570010&partnerID=8YFLogxK

U2 - 10.1021/jp2056442

DO - 10.1021/jp2056442

M3 - Article

AN - SCOPUS:80052570010

SN - 1932-7447

VL - 115

SP - 17774

EP - 17781

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

IS - 36

ER -

Functionalization of SBA-15 mesoporous materials using "thiol-ene click" Michael addition reaction

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this