Abstract
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).
Highlights
Many examples of molecular logic are already known, we demonstrate the diversity of our systems which can act as different gates or mimic more complex operations
The dual enzyme probe 1 constitutes an efficient tool for monitoring orthogonal enzymatic activities producing four distinct emission colors which are distinguishable even by the naked human eye
It can act as an individual probe for two different enzymes, allowing for their identification on the basis of different fluorescence colors, and can indicate the presence of both enzymes as well
Summary
Information processing with optical probes enables rapid and sensitive detection of different analytes in biochemical and supramolecular systems.[1,2,3] Fluorogenic substrates, which represent a logic YES-gate, are widely used for the detection and activity determination of enzymes due to the high sensitivity of fluorescence based methods.[1,4,5,6,7,8,9] Yet, measurements with on– off probes impose complications in quantification,[10,11] which are largely overcome by the use of dual-emissive probes, i.e. a YES and a NOT gate in a single molecule.[2,3,11,12,13,14,15,16] Enzymes with their fundamental importance for the function of biological systems are one of the key objectives of these probes. After incubation with 1, the output of the green channel (λdet = 500–530 nm, Fig. 2(e and f )) in combination with a suitable threshold value and the esterase/phosphatase activity as inputs represents an AND gate within the cell cluster as previously shown.[22] In contrast to fluorogenic systems[22,51] our multi-wavelength probe enables the read-out of more gates like INHIB (λdet = 565–615 nm, Fig. 2(g and h)) without further effort, providing additional information.
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