An ESR and MO study of stable triplet diphenylmethylene with perpendicular conformations

Katsuhiko Furukawa, Yoshio Teki, Takeji Takui, Koichi Itoh, Tetsuya Watanabe, Katsuyuki Hirai, Hideo Tomioka

Research output: Contribution to journalArticle

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Abstract

A ground-state triplet diphenylmethylene derivative, 2,2',3,3',5,5',6,6'-octamethyldiphenylmethylene (OMDPM) is a model for chemically stable organic high spin molecules. The electronic structure and the stability of OMDPM have been investigated by electron spin resonance, and the molecular conformation responsible for this stability has been shown by AM1 UHF MO calculations and LCAO MO calculations for zero-field splitting parameters. OMDPM was generated by photolysis of the corresponding diazo precursor in organic solvents or single crystals of the precursor at cryogenic temperatures. Based on the simulation of the fine-structure spectra from random orientation, the zero-field splitting parameters have been determined. The single-crystal experiment showed that OMDPM survived up to 250K. The AMI UHF MO calculations and the LCAO MO calculations made clear the reason of this stability. Both calculations indicated that the phenyl rings of OMDPM were perpendicular to each other and that the reactive center was protected by the eight methyl groups.

Original languageEnglish
Pages (from-to)183-190
Number of pages8
JournalMolecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals
Volume271
Issue number1
DOIs
Publication statusPublished - Sep 1 1995
Externally publishedYes

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Paramagnetic resonance
Conformations
Single crystals
single crystals
Photolysis
cryogenic temperature
Cryogenics
Organic solvents
Ground state
Electronic structure
photolysis
electron paramagnetic resonance
fine structure
electronic structure
Derivatives
Molecules
ground state
rings
crystals
molecules

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics

Cite this

An ESR and MO study of stable triplet diphenylmethylene with perpendicular conformations. / Furukawa, Katsuhiko; Teki, Yoshio; Takui, Takeji; Itoh, Koichi; Watanabe, Tetsuya; Hirai, Katsuyuki; Tomioka, Hideo.

In: Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, Vol. 271, No. 1, 01.09.1995, p. 183-190.

Research output: Contribution to journalArticle

Furukawa, Katsuhiko ; Teki, Yoshio ; Takui, Takeji ; Itoh, Koichi ; Watanabe, Tetsuya ; Hirai, Katsuyuki ; Tomioka, Hideo. / An ESR and MO study of stable triplet diphenylmethylene with perpendicular conformations. In: Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals. 1995 ; Vol. 271, No. 1. pp. 183-190.
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AU - Watanabe, Tetsuya

AU - Hirai, Katsuyuki

AU - Tomioka, Hideo

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AB - A ground-state triplet diphenylmethylene derivative, 2,2',3,3',5,5',6,6'-octamethyldiphenylmethylene (OMDPM) is a model for chemically stable organic high spin molecules. The electronic structure and the stability of OMDPM have been investigated by electron spin resonance, and the molecular conformation responsible for this stability has been shown by AM1 UHF MO calculations and LCAO MO calculations for zero-field splitting parameters. OMDPM was generated by photolysis of the corresponding diazo precursor in organic solvents or single crystals of the precursor at cryogenic temperatures. Based on the simulation of the fine-structure spectra from random orientation, the zero-field splitting parameters have been determined. The single-crystal experiment showed that OMDPM survived up to 250K. The AMI UHF MO calculations and the LCAO MO calculations made clear the reason of this stability. Both calculations indicated that the phenyl rings of OMDPM were perpendicular to each other and that the reactive center was protected by the eight methyl groups.

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