Facile synthesis of 2,5-bis(silyl)selenophene-1,1-dioxide and its photophysical properties

Toshiyuki Masuda; Yusuke Inagaki; Hiroyuki Momma; Eunsang Kwon; Wataru Setaka

doi:10.1039/c6nj01886f

Facile synthesis of 2,5-bis(silyl)selenophene-1,1-dioxide and its photophysical properties

Toshiyuki Masuda, Yusuke Inagaki, Hiroyuki Momma, Eunsang Kwon, Wataru Setaka

SCI - Research and Analytical Center for Giant Molecules

Tokyo Metropolitan University

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

8 Citations (Scopus)

Abstract

2,5-Bis(trimethylsilyl)selenophene-1,1-dioxide was easily synthesized in 80% yield by reaction of selenophene with the common oxidant m-chloroperbenzoic acid (mCPBA). The oxidation proceeded as a typical consecutive reaction. The kinetic study revealed that the rate of the first oxidation is faster than that of the second oxidation. The structure of the dioxide was identified by NMR spectroscopy and X-ray crystallography. The structural parameters of the dioxide show lower aromaticity as compared with that of selenophene. The HOMO-LUMO transition of the dioxide is remarkably red-shifted as compared with that of selenophene, because of the interactions between the π-orbitals of the ring and the p-orbitals of the oxygen atoms. A dichloromethane solution of the dioxide showed weak fluorescence due to the heavy-atom effect.

Original language	English
Pages (from-to)	8593-8599
Number of pages	7
Journal	New Journal of Chemistry
Volume	40
Issue number	10
DOIs	https://doi.org/10.1039/c6nj01886f
Publication status	Published - 2016

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title = "Facile synthesis of 2,5-bis(silyl)selenophene-1,1-dioxide and its photophysical properties",

abstract = "2,5-Bis(trimethylsilyl)selenophene-1,1-dioxide was easily synthesized in 80% yield by reaction of selenophene with the common oxidant m-chloroperbenzoic acid (mCPBA). The oxidation proceeded as a typical consecutive reaction. The kinetic study revealed that the rate of the first oxidation is faster than that of the second oxidation. The structure of the dioxide was identified by NMR spectroscopy and X-ray crystallography. The structural parameters of the dioxide show lower aromaticity as compared with that of selenophene. The HOMO-LUMO transition of the dioxide is remarkably red-shifted as compared with that of selenophene, because of the interactions between the π-orbitals of the ring and the p-orbitals of the oxygen atoms. A dichloromethane solution of the dioxide showed weak fluorescence due to the heavy-atom effect.",

author = "Toshiyuki Masuda and Yusuke Inagaki and Hiroyuki Momma and Eunsang Kwon and Wataru Setaka",

note = "Funding Information: This work was supported by a JSPS Grant-in-Aid for Scientific Research on Innovation Areas {"}stimuli-responsive chemical species{"} (WS, no. 15H00955) and Scientific Research (B) (WS, no. 25288042). Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

year = "2016",

doi = "10.1039/c6nj01886f",

language = "English",

volume = "40",

pages = "8593--8599",

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T1 - Facile synthesis of 2,5-bis(silyl)selenophene-1,1-dioxide and its photophysical properties

AU - Masuda, Toshiyuki

AU - Inagaki, Yusuke

AU - Momma, Hiroyuki

AU - Kwon, Eunsang

AU - Setaka, Wataru

N1 - Funding Information: This work was supported by a JSPS Grant-in-Aid for Scientific Research on Innovation Areas "stimuli-responsive chemical species" (WS, no. 15H00955) and Scientific Research (B) (WS, no. 25288042). Publisher Copyright: © 2016 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

PY - 2016

Y1 - 2016

N2 - 2,5-Bis(trimethylsilyl)selenophene-1,1-dioxide was easily synthesized in 80% yield by reaction of selenophene with the common oxidant m-chloroperbenzoic acid (mCPBA). The oxidation proceeded as a typical consecutive reaction. The kinetic study revealed that the rate of the first oxidation is faster than that of the second oxidation. The structure of the dioxide was identified by NMR spectroscopy and X-ray crystallography. The structural parameters of the dioxide show lower aromaticity as compared with that of selenophene. The HOMO-LUMO transition of the dioxide is remarkably red-shifted as compared with that of selenophene, because of the interactions between the π-orbitals of the ring and the p-orbitals of the oxygen atoms. A dichloromethane solution of the dioxide showed weak fluorescence due to the heavy-atom effect.

AB - 2,5-Bis(trimethylsilyl)selenophene-1,1-dioxide was easily synthesized in 80% yield by reaction of selenophene with the common oxidant m-chloroperbenzoic acid (mCPBA). The oxidation proceeded as a typical consecutive reaction. The kinetic study revealed that the rate of the first oxidation is faster than that of the second oxidation. The structure of the dioxide was identified by NMR spectroscopy and X-ray crystallography. The structural parameters of the dioxide show lower aromaticity as compared with that of selenophene. The HOMO-LUMO transition of the dioxide is remarkably red-shifted as compared with that of selenophene, because of the interactions between the π-orbitals of the ring and the p-orbitals of the oxygen atoms. A dichloromethane solution of the dioxide showed weak fluorescence due to the heavy-atom effect.

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JO - New Journal of Chemistry

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IS - 10

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Facile synthesis of 2,5-bis(silyl)selenophene-1,1-dioxide and its photophysical properties

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