Neutral rhodol-based dyes expressing localization in mitochondria.

Neutral rhodol-based red emitters are shown to efficiently localize in mitochondria, as demonstrated by confocal microscopy and co-localization studies. A simple model is proposed to explain the localization mechanism of neutral molecules. The model takes into account the strong coupling between the molecular dipole moment and the electric field of the inner mitochondrial membrane.

Polarized, V-Shaped, and Conjoined Biscoumarins: From Lack of Dipole Moment Alignment to High Brightness.

Eleven conjoined coumarins possessing a chromeno[3,4-]chromene-6,7-dione skeleton have been synthesized via the reaction of electron-rich phenols with esters of coumarin-3-carboxylic acids, catalyzed by either Lewis acids or 4-dimethylaminopyridine. Furthermore, Michael-type addition to angular benzo[]coumarins is possible, leading to conjugated helical systems. Arrangement of the electron-donating amino groups at diverse positions on this heterocyclic skeleton makes it possible to obtain π-expanded coumarins with emission either sensitive to, or entirely independent of, solvent polarity with large Stokes shifts.

Direct transformation of coumarins into orange-red emitting rhodols.

The lactone carbonyl group of coumarin derivatives has been shown to participate in intramolecular Knoevenagel condensations, enabling the unprecedented direct transformation of coumarins into rhodols. The resulting rhodols, possessing two ester groups, have very intense orange-red fluorescence.

Red emissive sulfone-rhodols as mitochondrial imaging agents.

The controlled hydrolysis of sulfone-rhodamines affords a series of core-modified red-emitting rhodols, the fluorescence of which is sensitive to solvent polarity with pronounced bathochromic shifts recorded in both DMSO and CH3CN combined with an up to 8-fold increase in the fluorescence quantum yield.

Rhodols - synthesis, photophysical properties and applications as fluorescent probes.

The formal replacement of one dialkylamino group in rhodamines with a hydroxyl group transforms them into rhodols. This apparently minor difference is not as small as one may think; rhodamines belong to the cyanine family whereas rhodols belong to merocyanines. Discovered in the late 19th century, rhodols have only very recently begun to gain momentum in the field of advanced fluorescence imaging.