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

Dengiz, Çağatay
SWAGER, Timothy M.
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.