Oxidative protonolysis of the expanded central CC bond in a di(spiroacridan)-type hexaphenylethane derivative accompanied by UVvis, FL, and CD spectral changes

Takanori Suzuki, Yusuke Kuroda, Kazuhisa Wada, Yuto Sakano, Ryo Katoono, Kenshu Fujiwara, Fumitoshi Kakiuchi, Takanori Fukushima

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12 Citations (Scopus)

Abstract

Upon electrochemical oxidation of configurationally stable (M)-4, 5-dimethyl-9, 10-dihydrophenanthrene attached with two spiroacridan units at the C9 and C10 positions [(M)-1c], a threeway-output response by UVvis, FL, and CD spectra was realized via clean conversion to the corresponding bond-dissociated dication (Rax)-2c2+. Similar gradual changes were induced upon standing of an aerated MeCN solution of (M)-1c after the addition of CF3CO2H because the elongated C9C10 bond was also cleaved by oxidative protonolysis to give (Rax)-2c2+.

Original languageEnglish
Pages (from-to)887-889
Number of pages3
JournalChemistry Letters
Volume43
Issue number6
DOIs
Publication statusPublished - 2014

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Electrochemical oxidation
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Oxidative protonolysis of the expanded central CC bond in a di(spiroacridan)-type hexaphenylethane derivative accompanied by UVvis, FL, and CD spectral changes. / Suzuki, Takanori; Kuroda, Yusuke; Wada, Kazuhisa; Sakano, Yuto; Katoono, Ryo; Fujiwara, Kenshu; Kakiuchi, Fumitoshi; Fukushima, Takanori.

In: Chemistry Letters, Vol. 43, No. 6, 2014, p. 887-889.

Research output: Contribution to journalArticle

Suzuki, Takanori ; Kuroda, Yusuke ; Wada, Kazuhisa ; Sakano, Yuto ; Katoono, Ryo ; Fujiwara, Kenshu ; Kakiuchi, Fumitoshi ; Fukushima, Takanori. / Oxidative protonolysis of the expanded central CC bond in a di(spiroacridan)-type hexaphenylethane derivative accompanied by UVvis, FL, and CD spectral changes. In: Chemistry Letters. 2014 ; Vol. 43, No. 6. pp. 887-889.
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abstract = "Upon electrochemical oxidation of configurationally stable (M)-4, 5-dimethyl-9, 10-dihydrophenanthrene attached with two spiroacridan units at the C9 and C10 positions [(M)-1c], a threeway-output response by UVvis, FL, and CD spectra was realized via clean conversion to the corresponding bond-dissociated dication (Rax)-2c2+. Similar gradual changes were induced upon standing of an aerated MeCN solution of (M)-1c after the addition of CF3CO2H because the elongated C9C10 bond was also cleaved by oxidative protonolysis to give (Rax)-2c2+.",
author = "Takanori Suzuki and Yusuke Kuroda and Kazuhisa Wada and Yuto Sakano and Ryo Katoono and Kenshu Fujiwara and Fumitoshi Kakiuchi and Takanori Fukushima",
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AU - Suzuki, Takanori

AU - Kuroda, Yusuke

AU - Wada, Kazuhisa

AU - Sakano, Yuto

AU - Katoono, Ryo

AU - Fujiwara, Kenshu

AU - Kakiuchi, Fumitoshi

AU - Fukushima, Takanori

PY - 2014

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AB - Upon electrochemical oxidation of configurationally stable (M)-4, 5-dimethyl-9, 10-dihydrophenanthrene attached with two spiroacridan units at the C9 and C10 positions [(M)-1c], a threeway-output response by UVvis, FL, and CD spectra was realized via clean conversion to the corresponding bond-dissociated dication (Rax)-2c2+. Similar gradual changes were induced upon standing of an aerated MeCN solution of (M)-1c after the addition of CF3CO2H because the elongated C9C10 bond was also cleaved by oxidative protonolysis to give (Rax)-2c2+.

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