Homoconjugated and Spiro Push-Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes

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Dengiz C., SWAGER T. M.

SYNLETT, vol.28, no.12, pp.1427-1431, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 12
  • Publication Date: 2017
  • Doi Number: 10.1055/s-0036-1588771
  • Journal Name: SYNLETT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1427-1431
  • Keywords: homoconjugation, cycloaddition, push-pull, quinones, spirocycles, CHROMOPHORES, TETRACYANOBUTADIENE, PI
  • Middle East Technical University Affiliated: No

Abstract

We report the synthesis and characterization of three new classes of push-pull chromophores using [2+2]-cycloaddition reactions of electron-rich alkynes and electron-poor alkenes. Previous investigations have focused on the reactions of cyano-substituted electron acceptors. This study demonstrates that cyano-free electron acceptors, naphtho- and anthradiquinones, can also be used to access extended push-pull systems. The effects of the structural changes on the spectroscopic and electronic properties were investigated by UV/vis spectroscopy. Structures were confirmed by X-ray and NMR analysis in solution.