Synthesis and properties of 1,8-Di(2-thienyl)-, 1,8-bis(5,2′-bithiophene-2-yl)-, 1,8-bis(5,2′:5′,2″-terthiophene-2-yl)-, and 1,8-bis(5,2′:5′,2″:5″,2″′-quaterthiophene-2-yl)naphthalenes and related compounds

Masami Kuroda, Juzo Nakayama, Masamatsu Hoshino, Noboru Furusho, Takashi Kawata, Shigeru Ohba

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

1,8-Di(2-thienyl)-, 1,8-bis(5,2′-bithiophene-2-yl)-, 1,8-bis(5,2′:5′,2″-terthiophene-2-yl)-, and 1,8-bis-(5,2′:5′,2″:5″,2″′-quaterthiophene-2-yl)naphthalenes (1a, 1b, 1c and 1d, respectively) were synthesized starting from 1,8-dibromonaphthalene by appliction of NiCl2(dppp)-catalyzed coupling of aryl bromides with thienylmagnesium bromides. For comparison with these compounds, 1-(2-thienyl)-, 1-(5,2′-bithiophene-2-yl)-, 1-(5,2′:5′,2″-terthiophene-2-yl)-, and 1-(5,2′:5′,2″:5″,2″′-quaterthiophene-2-yl)naphthalenes (2a-d) were also prepared. Inspection of 1H and 13C NMR and UV/Vis data of 1a-d and 2a-d including X-ray single crystal structure data of 1b suggests that the planes of two oligothiophene units of 1a-d are approximately parallel to each other and are at large angles to the naphthalene ring. In accordance with these findings, CV oxidation potential data show that the radical cations formed from 1a-d are stabilized by intramolecular electron transfer interaction of the two oligothiophene units.

Original languageEnglish
Pages (from-to)3735-3748
Number of pages14
JournalTetrahedron
Volume49
Issue number18
DOIs
Publication statusPublished - 1993 Apr 30

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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