ジスピロ[4,5-ジブロモ-9,10-ジヒドロフェナントレン-9,9':10,9'-ビキサンテン]類のエレクトロキロオプティカル応答

Translated title of the contribution: Electrochiroptical Response of Dispiro[4,5-dibromo-9,10-dihydrophenanthrene-9,9':10,9'-bixanthene] Derivatives

鈴木 孝紀, 山本 理絵, 樋口 博紀, 廣田 恵理果, 大北 雅一, 辻 孝

Research output: Contribution to journalArticle

Abstract

Upon two-electron oxidation of the title electron donor 1a, the elongated central C9-C10 bond was cleaved to give the biphenyl-2,2'-diyl bis(9-xanthenylium) dye 2a2+, which regenerated the colorless dispiro compound 1a by two-electron reduction. Presence of isosbestic points in the UV-Vis spectra during the electrochemical oxidation of 1a to 2a2+ indicates the negligible steady-state concentration of the intermediary cation radical. Interconversion between optically resolved 1a and 2a2+ is accompanied by drastic changes in CD spectra again with several isosbestic points, and racemization of (<I>P</I>),(<I>M</I>)-1a and (<I>S</I>),( <I>R</I>)-2a2+ does not occur at ambient conditions. This redox pair represents a new motif for the multi-output response system, where the electrochemical input is transduced into two independent spectral outputs.
Original languageUndefined/Unknown
Pages (from-to)1022-1022
Number of pages1
Journal基礎有機化学討論会要旨集(基礎有機化学連合討論会予稿集)
Volume16
Issue number0
DOIs
Publication statusPublished - 2002

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Derivatives
Electrons
Electrochemical oxidation
Cations
Coloring Agents
Oxidation
Oxidation-Reduction
diphenyl

Cite this

ジスピロ[4,5-ジブロモ-9,10-ジヒドロフェナントレン-9,9':10,9'-ビキサンテン]類のエレクトロキロオプティカル応答. / 鈴木孝紀; 山本理絵; 樋口博紀; 廣田恵理果; 大北雅一; 辻孝.

In: 基礎有機化学討論会要旨集(基礎有機化学連合討論会予稿集), Vol. 16, No. 0, 2002, p. 1022-1022.

Research output: Contribution to journalArticle

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title = "ジスピロ[4,5-ジブロモ-9,10-ジヒドロフェナントレン-9,9':10,9'-ビキサンテン]類のエレクトロキロオプティカル応答",
abstract = "Upon two-electron oxidation of the title electron donor 1a, the elongated central C9-C10 bond was cleaved to give the biphenyl-2,2'-diyl bis(9-xanthenylium) dye 2a2+, which regenerated the colorless dispiro compound 1a by two-electron reduction. Presence of isosbestic points in the UV-Vis spectra during the electrochemical oxidation of 1a to 2a2+ indicates the negligible steady-state concentration of the intermediary cation radical. Interconversion between optically resolved 1a and 2a2+ is accompanied by drastic changes in CD spectra again with several isosbestic points, and racemization of (<I>P),(<I>M)-1a and (<I>S),( <I>R)-2a2+ does not occur at ambient conditions. This redox pair represents a new motif for the multi-output response system, where the electrochemical input is transduced into two independent spectral outputs.",
author = "孝紀 鈴木 and 理絵 山本 and 博紀 樋口 and 恵理果 廣田 and 雅一 大北 and 孝 辻",
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T1 - ジスピロ[4,5-ジブロモ-9,10-ジヒドロフェナントレン-9,9':10,9'-ビキサンテン]類のエレクトロキロオプティカル応答

AU - 鈴木, 孝紀

AU - 山本, 理絵

AU - 樋口, 博紀

AU - 廣田, 恵理果

AU - 大北, 雅一

AU - 辻, 孝

PY - 2002

Y1 - 2002

N2 - Upon two-electron oxidation of the title electron donor 1a, the elongated central C9-C10 bond was cleaved to give the biphenyl-2,2'-diyl bis(9-xanthenylium) dye 2a2+, which regenerated the colorless dispiro compound 1a by two-electron reduction. Presence of isosbestic points in the UV-Vis spectra during the electrochemical oxidation of 1a to 2a2+ indicates the negligible steady-state concentration of the intermediary cation radical. Interconversion between optically resolved 1a and 2a2+ is accompanied by drastic changes in CD spectra again with several isosbestic points, and racemization of (<I>P),(<I>M)-1a and (<I>S),( <I>R)-2a2+ does not occur at ambient conditions. This redox pair represents a new motif for the multi-output response system, where the electrochemical input is transduced into two independent spectral outputs.

AB - Upon two-electron oxidation of the title electron donor 1a, the elongated central C9-C10 bond was cleaved to give the biphenyl-2,2'-diyl bis(9-xanthenylium) dye 2a2+, which regenerated the colorless dispiro compound 1a by two-electron reduction. Presence of isosbestic points in the UV-Vis spectra during the electrochemical oxidation of 1a to 2a2+ indicates the negligible steady-state concentration of the intermediary cation radical. Interconversion between optically resolved 1a and 2a2+ is accompanied by drastic changes in CD spectra again with several isosbestic points, and racemization of (<I>P),(<I>M)-1a and (<I>S),( <I>R)-2a2+ does not occur at ambient conditions. This redox pair represents a new motif for the multi-output response system, where the electrochemical input is transduced into two independent spectral outputs.

U2 - 10.11494/kisoyuki.16.0.1022.0

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