Synthesis and properties of ferrocenylmethylene-bridged calix[4]azulene and a new example of bis(1-azulenyl)ferrocenylmethylium ion

Taku Shoji; Junya Higashi; Shunji Ito; Kozo Toyota; Takeaki Iwamoto; Noboru Morita

doi:10.1002/ejoc.200900741

Synthesis and properties of ferrocenylmethylene-bridged calix[4]azulene and a new example of bis(1-azulenyl)ferrocenylmethylium ion

Taku Shoji, Junya Higashi, Shunji Ito, Kozo Toyota, Takeaki Iwamoto, Noboru Morita

SCI - Chemistry

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

11 Citations (Scopus)

Abstract

Ferrocenylmethylene-bridged calix[4]azulene derivative 3 and bis(1-azulenyl)ferrocenylmet:hane derivative 4 were obtained by the reaction of 6-tert-butylazulene (6) with ferrocenecarbaldehyde (7) in acetic acid. The new bis(l-azulenyl)ferrocenylmethylium ion 5⁺ was also generated, by the hydride abstraction reaction of the corresponding hydro derivative 4 with DDQ. The novel ferrocene-substituted calix[4J-azulene derivative 3 exhibit a reversible one-step multi-electron oxidation upon cyclic voltammetry.

Original language	English
Pages (from-to)	5948-5952
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	34
DOIs	https://doi.org/10.1002/ejoc.200900741
Publication status	Published - 2009 Dec 3

Keywords

Azulene
Calixarenes
Carbocations
Electrochemistry
UV/Vis spectroscopy

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and properties of ferrocenylmethylene-bridged calix[4]azulene and a new example of bis(1-azulenyl)ferrocenylmethylium ion",

abstract = "Ferrocenylmethylene-bridged calix[4]azulene derivative 3 and bis(1-azulenyl)ferrocenylmet:hane derivative 4 were obtained by the reaction of 6-tert-butylazulene (6) with ferrocenecarbaldehyde (7) in acetic acid. The new bis(l-azulenyl)ferrocenylmethylium ion 5+ was also generated, by the hydride abstraction reaction of the corresponding hydro derivative 4 with DDQ. The novel ferrocene-substituted calix[4J-azulene derivative 3 exhibit a reversible one-step multi-electron oxidation upon cyclic voltammetry.",

keywords = "Azulene, Calixarenes, Carbocations, Electrochemistry, UV/Vis spectroscopy",

author = "Taku Shoji and Junya Higashi and Shunji Ito and Kozo Toyota and Takeaki Iwamoto and Noboru Morita",

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AU - Shoji, Taku

AU - Higashi, Junya

AU - Ito, Shunji

AU - Toyota, Kozo

AU - Iwamoto, Takeaki

AU - Morita, Noboru

PY - 2009/12/3

Y1 - 2009/12/3

N2 - Ferrocenylmethylene-bridged calix[4]azulene derivative 3 and bis(1-azulenyl)ferrocenylmet:hane derivative 4 were obtained by the reaction of 6-tert-butylazulene (6) with ferrocenecarbaldehyde (7) in acetic acid. The new bis(l-azulenyl)ferrocenylmethylium ion 5+ was also generated, by the hydride abstraction reaction of the corresponding hydro derivative 4 with DDQ. The novel ferrocene-substituted calix[4J-azulene derivative 3 exhibit a reversible one-step multi-electron oxidation upon cyclic voltammetry.

AB - Ferrocenylmethylene-bridged calix[4]azulene derivative 3 and bis(1-azulenyl)ferrocenylmet:hane derivative 4 were obtained by the reaction of 6-tert-butylazulene (6) with ferrocenecarbaldehyde (7) in acetic acid. The new bis(l-azulenyl)ferrocenylmethylium ion 5+ was also generated, by the hydride abstraction reaction of the corresponding hydro derivative 4 with DDQ. The novel ferrocene-substituted calix[4J-azulene derivative 3 exhibit a reversible one-step multi-electron oxidation upon cyclic voltammetry.

KW - Azulene

KW - Calixarenes

KW - Carbocations

KW - Electrochemistry

KW - UV/Vis spectroscopy

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Synthesis and properties of ferrocenylmethylene-bridged calix[4]azulene and a new example of bis(1-azulenyl)ferrocenylmethylium ion

Abstract

Keywords

ASJC Scopus subject areas

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