Electronic structures and redox properties of silylmethylated C60

Hideo Nagashima; Masayuki Saito; Yoshiyuki Kato; Hitoshi Goto; Eiji Osawa; Masaaki Haga; Kenji Itoh

doi:10.1016/0040-4020(96)00113-5

Electronic structures and redox properties of silylmethylated C₆₀

Hideo Nagashima, Masayuki Saito, Yoshiyuki Kato, Hitoshi Goto, Eiji Osawa, Masaaki Haga, Kenji Itoh

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

14 Citations (Scopus)

Abstract

Theoretical and electrochemical studies were performed to understand the electronic structure and the redox property of two types of silylmethylated C₆₀, C₆₀(H)(CH₂SiMe₂Y) (1) and C₆₀(CH₂SiMe₂Y)₂ (2) [Y = alkyl, aryl, OR, F]. Semi-empirical molecular orbital (MO) calculations for 1a (Y = Me of 1) and 2a (Y = Me of 2), and their model compounds, C₆₀(H)(Me) (3) and C₆₀(Me)₂ (4) revealed the thermodynamically most stable isomer of each compound. Cyclic voltammograms showed three to five reversible reduction waves and a quasi-reversible oxidation wave; the redox potentials are consistent with those expected from frontier orbital energies calculated by AM1.

Original language	English
Pages (from-to)	5053-5064
Number of pages	12
Journal	Tetrahedron
Volume	52
Issue number	14
DOIs	https://doi.org/10.1016/0040-4020(96)00113-5
Publication status	Published - Apr 1 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Electronic structures and redox properties of silylmethylated C60",

abstract = "Theoretical and electrochemical studies were performed to understand the electronic structure and the redox property of two types of silylmethylated C60, C60(H)(CH2SiMe2Y) (1) and C60(CH2SiMe2Y)2 (2) [Y = alkyl, aryl, OR, F]. Semi-empirical molecular orbital (MO) calculations for 1a (Y = Me of 1) and 2a (Y = Me of 2), and their model compounds, C60(H)(Me) (3) and C60(Me)2 (4) revealed the thermodynamically most stable isomer of each compound. Cyclic voltammograms showed three to five reversible reduction waves and a quasi-reversible oxidation wave; the redox potentials are consistent with those expected from frontier orbital energies calculated by AM1.",

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T1 - Electronic structures and redox properties of silylmethylated C60

AU - Nagashima, Hideo

AU - Saito, Masayuki

AU - Kato, Yoshiyuki

AU - Goto, Hitoshi

AU - Osawa, Eiji

AU - Haga, Masaaki

AU - Itoh, Kenji

PY - 1996/4/1

Y1 - 1996/4/1

N2 - Theoretical and electrochemical studies were performed to understand the electronic structure and the redox property of two types of silylmethylated C60, C60(H)(CH2SiMe2Y) (1) and C60(CH2SiMe2Y)2 (2) [Y = alkyl, aryl, OR, F]. Semi-empirical molecular orbital (MO) calculations for 1a (Y = Me of 1) and 2a (Y = Me of 2), and their model compounds, C60(H)(Me) (3) and C60(Me)2 (4) revealed the thermodynamically most stable isomer of each compound. Cyclic voltammograms showed three to five reversible reduction waves and a quasi-reversible oxidation wave; the redox potentials are consistent with those expected from frontier orbital energies calculated by AM1.

AB - Theoretical and electrochemical studies were performed to understand the electronic structure and the redox property of two types of silylmethylated C60, C60(H)(CH2SiMe2Y) (1) and C60(CH2SiMe2Y)2 (2) [Y = alkyl, aryl, OR, F]. Semi-empirical molecular orbital (MO) calculations for 1a (Y = Me of 1) and 2a (Y = Me of 2), and their model compounds, C60(H)(Me) (3) and C60(Me)2 (4) revealed the thermodynamically most stable isomer of each compound. Cyclic voltammograms showed three to five reversible reduction waves and a quasi-reversible oxidation wave; the redox potentials are consistent with those expected from frontier orbital energies calculated by AM1.

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