Peripherally substituted tetradecaazaheptacene (N 14 Hp) compounds, exhibiting amphiprotism-coupled emission, have been synthesized. X-ray crystallography reveals a planar acene-like chromophore, and electronic absorption and emission occur in the near infrared biological transparency window (650 -900 nm). The compounds exhibit long wave emission with photoluminescence quantum yields Φ PL up to ~0.61 at 686 nm with monodeprotonated state Φ PL ~0.58 at 712 nm. This unprecedented highly

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... s chromophore illustrates the stability and utility of the pyrazinacenes for different applications based on their photophysical properties and chemical structures.