Formation of naphthodithiophene isomers by flash vacuum pyrolysis of 1,6-di(2-thienyl)- and 1,6-di(3-thienyl)-1,5-hexadien-3-ynes

Rui Umeda, Hiroshi Fukuda, Koji Miki, S. M.Abdur Rahman, Motohiro Sonoda, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

To develop a synthetic method of thiophene-based polycyclic aromatic compounds, we investigated the tandem cyclization of 1,6-dithienyl-1,5-hexadien-3-ynes under flash vacuum pyrolysis (FVP) conditions at high temperatures (850 or 1050 °C). As a result, several isomeric naphthodithiophene derivatives were obtained as mixtures, from which a few isomers were isolated. The structural assignments of the products were performed on the basis of combination of the experimental and calculated 1 H NMR chemical shifts of either purified products or mixtures of them. Plausible mechanisms for the formation of the products are proposed.

Original languageEnglish
Pages (from-to)378-384
Number of pages7
JournalComptes Rendus Chimie
Volume12
Issue number3-4
DOIs
StatePublished - 1 Mar 2009

Keywords

  • C-C bond formation
  • Cyclization
  • Flash vacuum pyrolysis
  • Naphthodithiophenes

Fingerprint Dive into the research topics of 'Formation of naphthodithiophene isomers by flash vacuum pyrolysis of 1,6-di(2-thienyl)- and 1,6-di(3-thienyl)-1,5-hexadien-3-ynes'. Together they form a unique fingerprint.

Cite this