Abstract
Proacetylenic: An aniline-based donor–acceptor-substituted butatriene exhibits not only cumulene-like dimerization to give a [4]radialene (λmax=756 nm), but also acetylene-like (proacetylenic) reactivity towards tetracyanoethene, affording via [2+2] cycloaddition–cycloreversion a NIR-absorbing zwitterionic chromophore (λmax=825 nm). The cationic charge on the imminium-type nitrogen in the zwitterion is evidenced by host–guest complexation with a tetraphosphonate cavitand.
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