Small Panchromatic and NIR Absorbers from Quinoid Zwitterions

The transamination of oxoaminobenzoquinonemonoimine (BQI derivatives), an unconventional zwitterionic quinone, allows isolation of a series of compounds featuring electron-donating aryl auxochromes. The substitution has a very strong impact on the electrochemical and optical features, which is rationalized by theoretical calculations. Protonation and alkylation of the BQIs toward the corresponding cations lead to surprising red-shifts of the absorption, especially in the instance of the most electron-rich dyes that exhibit panchromatic absorption spanning up to the near-infrared (NIR) region, a remarkable achievement for such small molecules.