Electronic properties, polymerization, and cycloaddition of 3,4,7,8-tetragermacycloocta-1,5-diyne and related compounds

Haruhiko Komoriya, Masahiro Kako, Yasuhiro Nakadaira, Kunio Mochida, Mari Kubota, Tsunetoshi Kobayashi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Permethylated 3,4,7,8-tetragermacycloocta-1,5-diyne (1) and 3,4-disila-7,8-digermacycloocta-1,5-diyne (2) were prepared. The photoelectron spectra of 1 and 2 were compared with that of their tetrasila analogue 3. The first ionization energy decreases in the order 3 > 2 > 1. Charge-transfer spectra of 1-tetracyanoethylene (TCNE), 2-TCNE and 3-TCNE complexes were observed. In CH2Cl2 containing TCNE 1 underwent oligomerization to give its higher homologues, and in CH3CN containing a catalytic amount of TCNE both 1 and 2 were polymerized to give the corresponding polymers almost quantitatively, whereas the sila analogue 3 was stable under these conditions. All compounds 1, 2 and 3 cycloadded to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give the corresponding 1 : 1 adducts in a [2 + 6] manner.

Original languageEnglish
Pages (from-to)123-129
Number of pages7
JournalJournal of Organometallic Chemistry
Volume499
Issue number1-2
Publication statusPublished - 1995 Sep 6

Fingerprint

Oligomerization
Cycloaddition
Ionization potential
Cycloaddition Reaction
cycloaddition
Photoelectrons
Polymerization
Electronic properties
Charge transfer
polymerization
analogs
quinones
Polymers
electronics
adducts
photoelectrons
charge transfer
ionization
polymers
tetracyanoethylene

Keywords

  • Charge transfer
  • Germanium
  • Group 14
  • Main Group metals
  • Photoelectron spectroscopy
  • Silicon

ASJC Scopus subject areas

  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

Electronic properties, polymerization, and cycloaddition of 3,4,7,8-tetragermacycloocta-1,5-diyne and related compounds. / Komoriya, Haruhiko; Kako, Masahiro; Nakadaira, Yasuhiro; Mochida, Kunio; Kubota, Mari; Kobayashi, Tsunetoshi.

In: Journal of Organometallic Chemistry, Vol. 499, No. 1-2, 06.09.1995, p. 123-129.

Research output: Contribution to journalArticle

Komoriya, Haruhiko ; Kako, Masahiro ; Nakadaira, Yasuhiro ; Mochida, Kunio ; Kubota, Mari ; Kobayashi, Tsunetoshi. / Electronic properties, polymerization, and cycloaddition of 3,4,7,8-tetragermacycloocta-1,5-diyne and related compounds. In: Journal of Organometallic Chemistry. 1995 ; Vol. 499, No. 1-2. pp. 123-129.
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