Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

Yoshinori Yamanoi; Tsukasa Usuki; Kenichiro Omoto; Masaki Shimada; Hikaru Koike; Munetaka Iwamura; Koichi Nozaki; Daisuke Saito; Masako Kato; Hiroshi Nishihara

doi:10.1016/j.tetlet.2019.03.033

Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

Yoshinori Yamanoi^*, Tsukasa Usuki, Kenichiro Omoto, Masaki Shimada, Hikaru Koike, Munetaka Iwamura, Koichi Nozaki, Daisuke Saito, Masako Kato, Hiroshi Nishihara

^*Corresponding author for this work

Program of Chemistry

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

1 Scopus citations

Abstract

Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (g _lum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.

Original language	English
Pages (from-to)	1108-1112
Number of pages	5
Journal	Tetrahedron Letters
Volume	60
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2019.03.033
State	Published - 2019/04/18

Keywords

Circularly polarized luminescence (CPL)
Dioxacyclophane
Luminescence
Organosilane compounds

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2019.03.033

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title = "Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials",

abstract = " Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (g lum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.",

keywords = "Circularly polarized luminescence (CPL), Dioxacyclophane, Luminescence, Organosilane compounds",

author = "Yoshinori Yamanoi and Tsukasa Usuki and Kenichiro Omoto and Masaki Shimada and Hikaru Koike and Munetaka Iwamura and Koichi Nozaki and Daisuke Saito and Masako Kato and Hiroshi Nishihara",

note = "Publisher Copyright: {\textcopyright} 2019",

year = "2019",

month = apr,

day = "18",

doi = "10.1016/j.tetlet.2019.03.033",

language = "英語",

volume = "60",

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T1 - Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

AU - Yamanoi, Yoshinori

AU - Usuki, Tsukasa

AU - Omoto, Kenichiro

AU - Shimada, Masaki

AU - Koike, Hikaru

AU - Iwamura, Munetaka

AU - Nozaki, Koichi

AU - Saito, Daisuke

AU - Kato, Masako

AU - Nishihara, Hiroshi

PY - 2019/4/18

Y1 - 2019/4/18

N2 - Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (g lum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.

AB - Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (g lum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.

KW - Circularly polarized luminescence (CPL)

KW - Dioxacyclophane

KW - Luminescence

KW - Organosilane compounds

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U2 - 10.1016/j.tetlet.2019.03.033

DO - 10.1016/j.tetlet.2019.03.033

M3 - 学術論文

AN - SCOPUS:85063087289

SN - 0040-4039

VL - 60

SP - 1108

EP - 1112

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

Abstract

Keywords

ASJC Scopus subject areas

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