Monomolecular pyrenol-derivatives as multi-emissive probes for orthogonal reactivities

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).

User Authorization at the Molecular Scale

“…The ability to create an entirely different family of molecular keypad locks, which utilize biological components, was first demonstrated by the group of Katz . Since then, a variety of molecular and biomolecular password systems that respond to biological inputs, such as to enzymes, proteins, and antibodies, have been developed, demonstrating novel mechanisms for differentiating among input sequences at the molecular level. An elegant bio‐security system, 3 , which combines an enzymatic cascade with a biofuel electrochemical cell, is described in Figure .…”

“…The latter are macroscopic analytical devices that, similar to the way the olfactory system operates, can interact non‐specifically with a wide range of analytes and discriminate among them by creating a wide range of unique identification patterns . Hence, the main difference between 8 and the molecular keypad locks discussed before is that instead of generating a single digital output (0 or 1) for each code entry, it associates each password with a unique emission “signature” that enables it to authorize multiple users.…”

Kinetic and spectroscopic responses of pH-sensitive nanoparticles: influence of the silica matrix

“…52 The full photochemical cycle following the photon absorption is known as the Förster cycle and is described in detail for pyranine-derived photoacids elsewhere. [50][51][52][53]61 ESPT in protic solvents is drastically slowed down when replacing water with methanol. 52 Similarly, the ESPT efficiency in deuterium oxide is lower by a factor of 2 to 5 than in that in water due to the kinetic isotope effect.…”

“…The correlation data were analyzed according to a previously described 2D diffusion model, including one or several dark states [eqn (4)]. 50,65 Here, g(s) denotes the obtained correlation function of the uorescence uctuations and N denotes the apparent particle number.…”

“…The synthesis of 5a, starting from 6-/8-bromopyrenol (1), is shown in Scheme 1. 50 The mixture of both regioisomers (1) was transformed into the corresponding sulfonesters. At this stage, the two isomers could be separated by chromatography, and the assignment of the substitution pattern of 2 was evident from the X-ray crystallographic analysis (ESI, Fig.…”