Monomolecular pyrenol-derivatives as multi-emissive probes for orthogonal reactivitiesThis work is dedicated to Andreas Zumbusch on the occasion of his 50th birthday.Electronic supplementary information (ESI) available: Further compound characterization, determination of enzyme kinetics, further preliminary live-cell experiments and details for molecular logic. CCDC 1443123. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6pp00290k

Photoacids on the basis of pyrenol have been extensively studied in the past 60 years. As their photophysical properties strongly depend on the substituents at the aromatic scaffold, we introduced two reactive moieties with different electronic coefficients thus creating multi-wavelength fluorescent probes. One probe is capable of monitoring two orthogonal transformations by four fluorescence colors, distinguishable even by the naked human eye. Another derivative can act as a three-color sensor for a wide range of different pH values. Both the presented compounds allow for mimicking of fundamental and advanced two-input logic operations due to the multi-wavelength emission. Furthermore, these compounds can process information in a logically reversible way (Feynman gate). Chameleons in a test tube: up to four easily distinguishable emission colors result from conversion by two hydrolytic enzymes at opposite reaction sites.