Synlett 2017; 28(12): 1427-1431
DOI: 10.1055/s-0036-1588771
© Georg Thieme Verlag Stuttgart · New York

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

Cagatay Dengiz, Timothy M. Swager*
  • Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA   Email:
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Publication History

Received: 31 January 2017

Accepted after revision: 08 March 2017

Publication Date:
11 April 2017 (eFirst)


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.

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