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

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 languageEnglish
Pages (from-to)5053-5064
Number of pages12
JournalTetrahedron
Volume52
Issue number14
DOIs
Publication statusPublished - Apr 1 1996

Fingerprint

Oxidation-Reduction
Electronic structure
Orbital calculations
Molecular orbitals
Isomers
Theoretical Models
Oxidation
fullerene C60

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Nagashima, H., Saito, M., Kato, Y., Goto, H., Osawa, E., Haga, M., & Itoh, K. (1996). Electronic structures and redox properties of silylmethylated C60. Tetrahedron, 52(14), 5053-5064. https://doi.org/10.1016/0040-4020(96)00113-5

Electronic structures and redox properties of silylmethylated C60. / Nagashima, Hideo; Saito, Masayuki; Kato, Yoshiyuki; Goto, Hitoshi; Osawa, Eiji; Haga, Masaaki; Itoh, Kenji.

In: Tetrahedron, Vol. 52, No. 14, 01.04.1996, p. 5053-5064.

Research output: Contribution to journal › Article

Nagashima, H, Saito, M, Kato, Y, Goto, H, Osawa, E, Haga, M & Itoh, K 1996, 'Electronic structures and redox properties of silylmethylated C60', Tetrahedron, vol. 52, no. 14, pp. 5053-5064. https://doi.org/10.1016/0040-4020(96)00113-5
Nagashima H, Saito M, Kato Y, Goto H, Osawa E, Haga M et al. Electronic structures and redox properties of silylmethylated C60. Tetrahedron. 1996 Apr 1;52(14):5053-5064. https://doi.org/10.1016/0040-4020(96)00113-5
Nagashima, Hideo ; Saito, Masayuki ; Kato, Yoshiyuki ; Goto, Hitoshi ; Osawa, Eiji ; Haga, Masaaki ; Itoh, Kenji. / Electronic structures and redox properties of silylmethylated C60. In: Tetrahedron. 1996 ; Vol. 52, No. 14. pp. 5053-5064.
@article{4917e2b3dc99432483fb604d80fe0726,
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.",
author = "Hideo Nagashima and Masayuki Saito and Yoshiyuki Kato and Hitoshi Goto and Eiji Osawa and Masaaki Haga and Kenji Itoh",
year = "1996",
month = "4",
day = "1",
doi = "10.1016/0040-4020(96)00113-5",
language = "English",
volume = "52",
pages = "5053--5064",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "14",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0029920313&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029920313&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(96)00113-5

DO - 10.1016/0040-4020(96)00113-5

M3 - Article

VL - 52

SP - 5053

EP - 5064

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 14

ER -

Access to Document