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Transforming Dyes into Fluorophores: Exciton-Induced Emission with Chain-like Oligo-BODIPY Superstructures.

ABSTRACT: Herein we present a systematic study demonstrating to which extent exciton formation can amplify fluorescence based on a series of ethylene-bridged oligo-BODIPYs. A set of non- and weakly fluorescent BODIPY motifs was selected and transformed into discrete, chain-like oligomers by linkage via a flexible ethylene tether. The prepared superstructures constitute excitonically active entities with non-conjugated, Coulomb-coupled oscillators. The non-radiative deactivation channels of Internal Conversion (IC), also combined with an upstream reductive Photoelectron Transfer (rPET) and Intersystem Crossing (ISC) were addressed at the monomeric state and the evolution of fluorescence and (non-)radiative decay rates studied along the oligomeric series. We demonstrate that a "masked" fluorescence can be fully reactivated irrespective of the imposed conformational rigidity. This work challenges the paradigm that a collective fluorescence enhancement is limited to sterically induced motional restrictions.

SUBMITTER: Patalag LJ

PROVIDER: S-EPMC9310714 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes.

Project description:Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700-1000 nm) and shortwave infrared (SWIR, 1000-1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible energy region. To tune these chromophores to the NIR region, fused nitrogen-based heterocyclic indolizine donors were added to a BODIPY scaffold. The indolizine BODIPY dyes were synthesized via microwave-assisted Knoevenagel condensation with indolizine aldehydes. The non-protonated dyes showed NIR absorption and emission at longer wavelengths than an aniline benchmark. Protonation of the dyes produced a dramatic 0.35 eV bathochromic shift (230 nm shift from 797 nm to 1027 nm) to give a SWIR absorption and emission (λmaxemis = 1061 nm). Deprotonation demonstrates that material emission is reversibly switchable between the NIR and SWIR.

| S-EPMC9919721 | biostudies-literature

BODIPY Fluorophores for Membrane Potential Imaging.

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| S-EPMC7285656 | biostudies-literature

Expeditious, mechanochemical synthesis of BODIPY dyes.

Project description:BODIPY dyes have been synthesized under solvent-free or essentially solvent-free conditions, within about 5 minutes in an open-to-air setup by using a pestle and mortar, with yields that are comparable to those obtained via traditional routes that typically require reaction times of several hours to days.

| S-EPMC3678757 | biostudies-other

High Affinity Neutral Bodipy Fluorophores for Mitochondrial Tracking.

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| S-EPMC6047038 | biostudies-literature

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| S-EPMC5906127 | biostudies-literature

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| S-EPMC4476635 | biostudies-literature

Functionalization of 3,5,8-trichlorinated BODIPY dyes.

Project description:Catalytic hydrogenation of dibenzyl 5-dipyrroketone-2,9-dicarboxylates followed by decarboxylative iodination affords a 2,9-diiododipyrroketone which gives a 2,5,9-trichlorodipyrromethene hydrochloride after nucleophilic addition/elimination, with adventitious chloride to replace the two iodide groups. Treatment with BF3·Et2O gives a 3,5,8-trichloro-BODIPY that readily undergoes regioselective Stille coupling at the 8-position, or homo/mixed couplings at the 3,8- or 3,5- and 8-positions. Stepwise and controlled replacement of the 3,5- and 8-chlorine atoms using Stille reagents results in formation of a completely unsymmetrical trisubstituted BODIPY. Several examples of unsymmetrical BODIPYs were synthesized and characterized using this methodology. Structure features of new BODIPYs are discussed within the context of 14 new X-ray structures, and photophysical parameters of all new BODIPY compounds are reported and discussed.

| S-EPMC4227577 | biostudies-literature

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| S-EPMC8267640 | biostudies-literature

Quantum Chemical Study Aimed at Modeling Efficient Aza-BODIPY NIR Dyes: Molecular and Electronic Structure, Absorption, and Emission Spectra.

Project description:A comprehensive study of the molecular structure of aza-BODIPY and its derivatives, obtained by introduction of one or more substituents, was carried out. We considered the changes in the characteristics of the electronic and geometric structure of the unsubstituted aza-BODIPY introducing the following substituents into the dipyrrin core; phenyl, 2-thiophenyl, 2-furanyl, 3-pyridinyl, 4-pyridinyl, 2-pyridinyl, and ethyl groups. The ground-state geometries of the unsubstituted Aza-BODIPY and 27 derivatives were computed at the PBE/6-31G(d) and CAM-B3LYP/6-31+G(d,p) levels of theory. The time-dependent density-functional theory (TDDFT) together with FC vibronic couplings was used to investigate their absorption and emission spectra.

| S-EPMC7698449 | biostudies-literature

Exciton Emission and Light induced Charge Separation in colloidal ZnO Nanocrystals.

Project description:Adsorption of organic molecules at ZnO nanoparticle surfaces enables the transfer of energy or charge across resulting organic-inorganic interfaces and, consequently, determines the optoelectronic performance of ZnO based hybrids. We investigated on aqueous colloidal ZnO dispersions adsorption-induced changes with photoluminescence (PL) and electron paramagnetic resonance (EPR) spectroscopy. Citrate and acetate ion adsorption increases or decreases radiative exciton annihilation at hν = 3.3 eV and at room temperature, respectively. Searching for a correspondence between PL emission and the yield of trapped charge carriers originating from exciton separation - using photon energies of hν = 4.6 eV and fluxes of = 1014 cm-2 s-1 for excitation - we found that there is a negligible fraction of paramagnetic products that originate from exciton separation. Upon polychromatic excitation with significantly higher photon fluxes (Ṅ ph = 1016 cm-2·s-1), ZnO specific shallow defects trap unpaired electrons in citrate and acetate functionalized samples. The adsorption dependent PL intensity changes and the excitation parameter dependent yield of separated charges (EPR) in colloidal ZnO nanoparticles underline that the distribution over the different exciton annihilation channels sensitively depends on interface composition and the intensity of the photoexcitation light.

| S-EPMC7116049 | biostudies-literature

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