Molecular structures and charge-transfer complexes of cis-dibenzo[c,h]-1,6-disilabicyclo[4.4.0]deca-3,8-dienes and bi(benzo[c]silacyclopent-3-ene-1-yl)s

Soichiro Kyushin, Masanobu Ikarugi, Satoshi Tsunakawa, Yukiko Izumi, Michihiro Miyake, Mitsuo Sato, Hideyuki Matsumoto, Midori Goto

Research output: Contribution to journalArticle

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Abstract

The reaction of the di-Grignard reagent of α,α′-dichloro-o-xylene with Cl2RSiSiRCl2(R iPr and Me) produced cis-dibenzo[c,h-1,6-dialkyl-1,6-disilabicyclo[4.4.O]deca-3,8-diene (1) and bi(benzo[c]-1-alkylsilacyclopent-3-ene-1-yl) (2). The structures of 1a (R iPr) and 2a (R iPr) were determined by X-ray crystallography. Crystal data for 1a: orthorhombic, Pbca, a = 14.816(1), b = 16.263(1), c = 17.257(1) Å, V = 4158.1(3) Å3, Z = 8, R = 0.040, Rw = 0.050 for 2008 reflections. Crystal data for 2a: triclinic, P1, a = 8.179(2), b = 10.389(3), c = 6.605(2) Å, α = 100.39(2)°, β = 98.29(2), γ = 106.75(2)°, V = 517.0(3) Å3, Z = 1, R = 0.042, Rw = 0.051 for 1167 reflections. Compounds 1 and 2 have relatively low oxidation potentials (1.24-1.59 V vs. SCE, in acetonitrile) and form charge-transfer complexes with tetracyanoethylene (TCNE). In the case of 2a, the charge-transfer complex was isolated as red crystals and the structure was determined by X-ray crystallography. Crystal data for the 2a-TCNE complex: triclinic, P1, a = 6.8399(8), b = 8.2836(6), c = 12.868(1) Å, α = 84.142(6)°, β = 88.737(6)°, γ = 66.801(8)°, V = 666.5(1) Å3, Z = 1, R = 0.038, Rw = 0.042 for 1554 reflections.

Original languageEnglish
Pages (from-to)19-27
Number of pages9
JournalJournal of Organometallic Chemistry
Volume473
Issue number1-2
DOIs
Publication statusPublished - Jun 28 1994
Externally publishedYes

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X Ray Crystallography
dienes
Molecular Structure
Molecular structure
Charge transfer
molecular structure
charge transfer
Crystals
X ray crystallography
crystallography
crystals
xylene
Xylene
Acetonitrile
acetonitrile
reagents
x rays
Oxidation
oxidation
tetracyanoethylene

Keywords

  • Charge transfer
  • Silicon

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

Molecular structures and charge-transfer complexes of cis-dibenzo[c,h]-1,6-disilabicyclo[4.4.0]deca-3,8-dienes and bi(benzo[c]silacyclopent-3-ene-1-yl)s. / Kyushin, Soichiro; Ikarugi, Masanobu; Tsunakawa, Satoshi; Izumi, Yukiko; Miyake, Michihiro; Sato, Mitsuo; Matsumoto, Hideyuki; Goto, Midori.

In: Journal of Organometallic Chemistry, Vol. 473, No. 1-2, 28.06.1994, p. 19-27.

Research output: Contribution to journalArticle

Kyushin, Soichiro ; Ikarugi, Masanobu ; Tsunakawa, Satoshi ; Izumi, Yukiko ; Miyake, Michihiro ; Sato, Mitsuo ; Matsumoto, Hideyuki ; Goto, Midori. / Molecular structures and charge-transfer complexes of cis-dibenzo[c,h]-1,6-disilabicyclo[4.4.0]deca-3,8-dienes and bi(benzo[c]silacyclopent-3-ene-1-yl)s. In: Journal of Organometallic Chemistry. 1994 ; Vol. 473, No. 1-2. pp. 19-27.
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abstract = "The reaction of the di-Grignard reagent of α,α′-dichloro-o-xylene with Cl2RSiSiRCl2(R iPr and Me) produced cis-dibenzo[c,h-1,6-dialkyl-1,6-disilabicyclo[4.4.O]deca-3,8-diene (1) and bi(benzo[c]-1-alkylsilacyclopent-3-ene-1-yl) (2). The structures of 1a (R iPr) and 2a (R iPr) were determined by X-ray crystallography. Crystal data for 1a: orthorhombic, Pbca, a = 14.816(1), b = 16.263(1), c = 17.257(1) {\AA}, V = 4158.1(3) {\AA}3, Z = 8, R = 0.040, Rw = 0.050 for 2008 reflections. Crystal data for 2a: triclinic, P1, a = 8.179(2), b = 10.389(3), c = 6.605(2) {\AA}, α = 100.39(2)°, β = 98.29(2), γ = 106.75(2)°, V = 517.0(3) {\AA}3, Z = 1, R = 0.042, Rw = 0.051 for 1167 reflections. Compounds 1 and 2 have relatively low oxidation potentials (1.24-1.59 V vs. SCE, in acetonitrile) and form charge-transfer complexes with tetracyanoethylene (TCNE). In the case of 2a, the charge-transfer complex was isolated as red crystals and the structure was determined by X-ray crystallography. Crystal data for the 2a-TCNE complex: triclinic, P1, a = 6.8399(8), b = 8.2836(6), c = 12.868(1) {\AA}, α = 84.142(6)°, β = 88.737(6)°, γ = 66.801(8)°, V = 666.5(1) {\AA}3, Z = 1, R = 0.038, Rw = 0.042 for 1554 reflections.",
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author = "Soichiro Kyushin and Masanobu Ikarugi and Satoshi Tsunakawa and Yukiko Izumi and Michihiro Miyake and Mitsuo Sato and Hideyuki Matsumoto and Midori Goto",
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T1 - Molecular structures and charge-transfer complexes of cis-dibenzo[c,h]-1,6-disilabicyclo[4.4.0]deca-3,8-dienes and bi(benzo[c]silacyclopent-3-ene-1-yl)s

AU - Kyushin, Soichiro

AU - Ikarugi, Masanobu

AU - Tsunakawa, Satoshi

AU - Izumi, Yukiko

AU - Miyake, Michihiro

AU - Sato, Mitsuo

AU - Matsumoto, Hideyuki

AU - Goto, Midori

PY - 1994/6/28

Y1 - 1994/6/28

N2 - The reaction of the di-Grignard reagent of α,α′-dichloro-o-xylene with Cl2RSiSiRCl2(R iPr and Me) produced cis-dibenzo[c,h-1,6-dialkyl-1,6-disilabicyclo[4.4.O]deca-3,8-diene (1) and bi(benzo[c]-1-alkylsilacyclopent-3-ene-1-yl) (2). The structures of 1a (R iPr) and 2a (R iPr) were determined by X-ray crystallography. Crystal data for 1a: orthorhombic, Pbca, a = 14.816(1), b = 16.263(1), c = 17.257(1) Å, V = 4158.1(3) Å3, Z = 8, R = 0.040, Rw = 0.050 for 2008 reflections. Crystal data for 2a: triclinic, P1, a = 8.179(2), b = 10.389(3), c = 6.605(2) Å, α = 100.39(2)°, β = 98.29(2), γ = 106.75(2)°, V = 517.0(3) Å3, Z = 1, R = 0.042, Rw = 0.051 for 1167 reflections. Compounds 1 and 2 have relatively low oxidation potentials (1.24-1.59 V vs. SCE, in acetonitrile) and form charge-transfer complexes with tetracyanoethylene (TCNE). In the case of 2a, the charge-transfer complex was isolated as red crystals and the structure was determined by X-ray crystallography. Crystal data for the 2a-TCNE complex: triclinic, P1, a = 6.8399(8), b = 8.2836(6), c = 12.868(1) Å, α = 84.142(6)°, β = 88.737(6)°, γ = 66.801(8)°, V = 666.5(1) Å3, Z = 1, R = 0.038, Rw = 0.042 for 1554 reflections.

AB - The reaction of the di-Grignard reagent of α,α′-dichloro-o-xylene with Cl2RSiSiRCl2(R iPr and Me) produced cis-dibenzo[c,h-1,6-dialkyl-1,6-disilabicyclo[4.4.O]deca-3,8-diene (1) and bi(benzo[c]-1-alkylsilacyclopent-3-ene-1-yl) (2). The structures of 1a (R iPr) and 2a (R iPr) were determined by X-ray crystallography. Crystal data for 1a: orthorhombic, Pbca, a = 14.816(1), b = 16.263(1), c = 17.257(1) Å, V = 4158.1(3) Å3, Z = 8, R = 0.040, Rw = 0.050 for 2008 reflections. Crystal data for 2a: triclinic, P1, a = 8.179(2), b = 10.389(3), c = 6.605(2) Å, α = 100.39(2)°, β = 98.29(2), γ = 106.75(2)°, V = 517.0(3) Å3, Z = 1, R = 0.042, Rw = 0.051 for 1167 reflections. Compounds 1 and 2 have relatively low oxidation potentials (1.24-1.59 V vs. SCE, in acetonitrile) and form charge-transfer complexes with tetracyanoethylene (TCNE). In the case of 2a, the charge-transfer complex was isolated as red crystals and the structure was determined by X-ray crystallography. Crystal data for the 2a-TCNE complex: triclinic, P1, a = 6.8399(8), b = 8.2836(6), c = 12.868(1) Å, α = 84.142(6)°, β = 88.737(6)°, γ = 66.801(8)°, V = 666.5(1) Å3, Z = 1, R = 0.038, Rw = 0.042 for 1554 reflections.

KW - Charge transfer

KW - Silicon

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