The Search for Highly Colored Organic Compounds

Until now the study of organic compounds in which the π-electron system is excited by absorbed light has been mainly concentrated on the ultraviolet and visible regions of the electromagnetic spectrum. Various new applications, such as the use of conjugated organic compounds as dye lasers or as materitals for storing information with the help of diode lasers, led to the synthesis of new compounds which absorb light in the near in infrared (NIR). It is possible to use structure-color relationships to predict the properties of such new compounds when they belong to dyestuff classes which have already been studied in detail; in this case the approach involves decreasing the energy difference between the ground state and the first excited state. A less conventional starting point is provided by molecular structures in which from the outset there is only a very small energy difference between the lowest-energy electronic states; such diradicaloid molecules occupy a special position among the various types of organic compounds. It is possible by means of suitable structural modification to stabilize such molecules in a singlet from which absorbs light at very long wavelengths (i.e. at small wave numbers).     

Anthracene-Fused Oligo-BODIPYs: A New Class of π-Extended NIR-Absorbing Materials

Large π-conjugated systems are key in the area of molecular materials. Herein, we prepare via Au^I-catalyzed cyclization a series of fully π-conjugated anthracene-fused oligo-BODIPYs. Their structural and optoelectronic properties were studied by several techniques, ranging from X-ray, UV/Vis, and cyclic voltammetry to transient absorption spectroscopy. As a complement, their electronic structures were explored by means of Density Functional Theory (DFT) calculations. Depending on the size and shape of the π-conjugated skeleton, unique features—such as face-to-face supramolecular organization, NIR absorption and fluorescence as well as strong electron accepting character—were noted. All in all, the aforementioned features render them valuable for technological applications.     

Organic Dyes in Laser Technology

Laser technology has been developed to a very high level since 1960. Significant advances have been made possible only by the use of organic dyes as optical shutters for the production of giant pulses. Ultrashort pulses in the picosecond range were first produced in 1966; their measurement was greatly facilitated by the use of organic dyes. Probably the most important recent advance in the laser field is the dye laser, which was first described in 1966, and in which the active medium is a solution of an organic dye.     

Coupling Principles in Organic Dyes

Dye molecules containing two or more polymethine structural units, or at least one polymethine and one polyene structural unit, generally exhibit coupling effects that determine the spectroscopic behavior and other physicochemical properties of the substance. The coupling concept can be used inter alia to fit the quinone dyestuffs, the indigoids, and the indanthrenes into a general poymethine color system and to perdict new dye structures.     

Photoactivatable Carbo- and Silicon-Rhodamines and Their Application in MINFLUX Nanoscopy

New photoactivatable fluorescent dyes (rhodamine, carbo- and silicon-rhodamines [SiR]) with emission ranging from green to far red have been prepared, and their photophysical properties studied. The photocleavable 2-nitrobenzyloxycarbonyl unit with an alpha-carboxyl group as a branching point and additional functionality was attached to a polycyclic and lipophilic fluorescent dye. The photoactivatable probes having the HaloTagTM amine (O2) ligand bound with a dye core were obtained and applied for live-cell staining in stable cell lines incorporating Vimentin (VIM) or Nuclear Pore Complex Protein NUP96 fused with the HaloTag. The probes were applied in 2D (VIM, NUP96) and 3D (VIM) MINFLUX nanoscopy, as well as in superresolution fluorescence microscopy with single fluorophore activation (VIM, live-cell labeling). Images of VIM and NUPs labeled with different dyes were acquired and their apparent dimensions and shapes assessed on a lower single-digit nanometer scale. Applicability and performance of the photoactivatable dye derivatives were evaluated in terms of photoactivation rate, labeling and detection efficiency, number of detected photons per molecule and other parameters related to MINFLUX nanoscopy.