Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enhanced Hypsochromic Shifts, Quantum Yield, and ?-? Interactions in a meso,?-Heteroaryl-Fused BODIPY.

ABSTRACT: We report the synthesis and investigation of an unprecedented 8-heteroaryl-fused BODIPY 4. This compound exhibits enhanced ?-? stacking in the solid state, unusually large blue-shifts in the absorbance and emission spectra, and higher fluorescence quantum yield than its unfused precursor; DFT calculations suggest a small energy gap for 4 and strong electronic communication between the 8-OPh and the BODIPY core.

SUBMITTER: Zhao N

PROVIDER: S-EPMC5507578 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Enhanced Hypsochromic Shifts, Quantum Yield, and π-π Interactions in a meso,β-Heteroaryl-Fused BODIPY.

Zhao Ning N Xuan Sunting S Fronczek Frank R FR Smith Kevin M KM Vicente M Graça H MG

The Journal of organic chemistry 20170310 7

We report the synthesis and investigation of an unprecedented 8-heteroaryl-fused BODIPY 4. This compound exhibits enhanced π-π stacking in the solid state, unusually large blue-shifts in the absorbance and emission spectra, and higher fluorescence quantum yield than its unfused precursor; DFT calculations suggest a small energy gap for 4 and strong electronic communication between the 8-OPh and the BODIPY core. ...[more]

PMID: 28231707

Similar Datasets

Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.

Project description:A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials.

| S-EPMC6693341 | biostudies-literature

Enhanced Room-Temperature Photoluminescence Quantum Yield in Morphology Controlled J-Aggregates.

Project description:Supramolecular assemblies from organic dyes forming J-aggregates are known to exhibit narrowband photoluminescence with full-width at half maximum of ≈9 nm (260 cm-1). Applications of these high color purity emitters, however, are hampered by the rather low photoluminescence quantum yields reported for cyanine J-aggregates, even when formed in solution. Here, it is demonstrated that cyanine J-aggregates can reach an order of magnitude higher photoluminescence quantum yield (increase from 5% to 60%) in blend solutions of water and alkylamines at room temperature. By means of time-resolved photoluminescence studies, an increase in the exciton lifetime as a result of the suppression of non-radiative processes is shown. Small-angle neutron scattering studies suggest a necessary condition for the formation of such highly emissive J-aggregates: the presence of a sharp water/amine interface for J-aggregate assembly and the coexistence of nanoscale-sized water and amine domains to restrict the J-aggregate size and solubilize monomers, respectively.

| S-EPMC7887577 | biostudies-literature

J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging.

Project description:J-aggregation is an efficient strategy for the development of fluorescent imaging agents in the second near-infrared window. However, the design of the second near-infrared fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso-[2.2]paracyclophanyl-3,5-bis-N,N-dimethylaminostyrl BODIPY (PCP-BDP2) as an example of BODIPY dye with J-aggregation induced the second near-infrared fluorescence. PCP-BDP2 shows an emission maximum at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY play key roles in the J-aggregation behavior and photophysical properties tuning. Notably, PCP-BDP2 J-aggregates can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study demonstrates BODIPY dye as an alternate J-aggregation platform for developing the second near-infrared imaging agents.

| S-EPMC8062432 | biostudies-literature

Chemiluminescence resonance energy transfer–based nanoparticles for quantum yield–enhanced cancer phototheranostics.

Project description:Chemiluminescence (CL) has recently gained attention for CL resonance energy transfer (CRET)–mediated photodynamic therapy of cancer. However, the short duration of the CL signal and low quantum yield of the photosensitizer have limited its translational applications. Here, we report CRET-based nanoparticles (CRET-NPs) to achieve quantum yield–enhanced cancer phototheranostics by reinterpreting the hidden nature of CRET. Owing to reactive oxygen species (ROS)–responsive CO2 generation, CRET-NPs were capable of generating a strong and long-lasting photoacoustic signal in the tumor tissue via thermal expansion–induced vaporization. In addition, the CRET phenomenon of the NPs enhanced ROS quantum yield of photosensitizer through both electron transfer for an oxygen-independent type I photochemical reaction and self-illumination for an oxygen-dependent type II photochemical reaction. Consequently, owing to their high ROS quantum yield, CRET-NPs effectively inhibited tumor growth with complete tumor growth inhibition in 60% of cases, even with a single treatment.

| S-EPMC7314564 | biostudies-literature

Purcell-enhanced quantum yield from carbon nanotube excitons coupled to plasmonic nanocavities.

Project description:Single-walled carbon nanotubes (SWCNTs) are promising absorbers and emitters to enable novel photonic applications and devices but are also known to suffer from low optical quantum yields. Here we demonstrate SWCNT excitons coupled to plasmonic nanocavity arrays reaching deeply into the Purcell regime with Purcell factors (F P) up to F P = 180 (average F P = 57), Purcell-enhanced quantum yields of 62% (average 42%), and a photon emission rate of 15 MHz into the first lens. The cavity coupling is quasi-deterministic since the photophysical properties of every SWCNT are enhanced by at least one order of magnitude. Furthermore, the measured ultra-narrow exciton linewidth (18 μeV) reaches the radiative lifetime limit, which is promising towards generation of transform-limited single photons. To demonstrate utility beyond quantum light sources we show that nanocavity-coupled SWCNTs perform as single-molecule thermometers detecting plasmonically induced heat at cryogenic temperatures in a unique interplay of excitons, phonons, and plasmons at the nanoscale.

| S-EPMC5680202 | biostudies-literature

Dual-resonance enhanced quantum light-matter interactions in deterministically coupled quantum-dot-micropillars.

Project description:Optical microcavities have widely been employed to enhance either the optical excitation or the photon emission processes for boosting light-matter interactions at the nanoscale. When both the excitation and emission processes are simultaneously facilitated by the optical resonances provided by the microcavities, as referred to the dual-resonance condition in this article, the performances of many nanophotonic devices approach to the optima. In this work, we present versatile accessing of dual-resonance conditions in deterministically coupled quantum-dot (QD)-micropillars, which enables emission from neutral exciton (X)-charged exciton (CX) transition with improved single-photon purity. In addition, the rarely observed up-converted single-photon emission process is achieved under dual-resonance conditions. We further exploit the vectorial nature of the high-order cavity modes to significantly improve the excitation efficiency under the dual-resonance condition. The dual-resonance enhanced light-matter interactions in the quantum regime provide a viable path for developing integrated quantum photonic devices based on cavity quantum electrodynamics (QED) effect, e.g., highly efficient quantum light sources and quantum logical gates.

| S-EPMC8322385 | biostudies-literature

Enhanced nonlinear interactions in quantum optomechanics via mechanical amplification.

Project description:The quantum nonlinear regime of optomechanics is reached when nonlinear effects of the radiation pressure interaction are observed at the single-photon level. This requires couplings larger than the mechanical frequency and cavity-damping rate, and is difficult to achieve experimentally. Here we show how to exponentially enhance the single-photon optomechanical coupling strength using only additional linear resources. Our method is based on using a large-amplitude, strongly detuned mechanical parametric drive to amplify mechanical zero-point fluctuations and hence enhance the radiation pressure interaction. It has the further benefit of allowing time-dependent control, enabling pulsed schemes. For a two-cavity optomechanical set-up, we show that our scheme generates photon blockade for experimentally accessible parameters, and even makes the production of photonic states with negative Wigner functions possible. We discuss how our method is an example of a more general strategy for enhancing boson-mediated two-particle interactions and nonlinearities.

| S-EPMC4848487 | biostudies-literature

Rapid syntheses of N-fused heterocycles via acyl-transfer in heteroaryl ketones.

Project description:The wide-ranging potencies of bioactive N-fused heterocycles inspire the development of synthetic transformations that simplify preparation of their complex, diverse structural motifs. Heteroaryl ketones are ubiquitous, readily available, and inexpensive molecular scaffolds, and are thus synthetically appealing as precursors in preparing N-fused heterocycles via intramolecular acyl-transfer. To best of our knowledge, acyl-transfer of unstrained heteroaryl ketones remains to be demonstrated. Here, we show an acyl transfer-annulation to convert heteroaryl ketones to N-fused heterocycles. Driven via aromatisation, the acyl of a heteroaryl ketone can be transferred from the carbon to the nitrogen of the corresponding heterocycle. The reaction commences with the spiroannulation of a heteroaryl ketone and an alkyl bromide, with the resulting spirocyclic intermediate undergoing aromatisation-driven intramolecular acyl transfer. The reaction conditions are optimised, with the reaction exhibiting a broad substrate scope in terms of the ketone and alkyl bromide. The utility of this protocol is further demonstrated via application to complex natural products and drug derivatives to yield heavily functionalised N-fused heterocycles.

| S-EPMC9184603 | biostudies-literature

Aza-BODIPY dyes with enhanced hydrophilicity.

Project description:Attempts to make a diamino disulfonic acid derivative of an aza-BODIPY showed it was difficult to add BF2 to a disulfonated azadipyrromethene, and sulfonation of an aza-BODIPY resulted in loss of the BF2 fragment. We conclude the electron-deficient character of aza-BODIPY dyes destabilizes them relative to BODIPY dyes. Consequently, sulfonation of the aza-BODIPY core is not a viable strategy to increase water solubility. This assertion was indirectly supported via stability studies of a BODIPY and an aza-BODIPY in aqueous media. To afford the desired compound type, an aza-BODIPY with two amino and two sulfonic acid groups was prepared via modification of the aryl substituents with cysteic acid.

| S-EPMC4476635 | biostudies-literature

meso-Antracenyl-BODIPY Dyad as a New Photocatalyst in Atom-Transfer Radical Addition Reactions.

Project description:We demonstrate that because of the efficient generation of triplet excited state under UV or visible-light irradiation, meso-antracenyl-BODIPY donor-acceptor dyad can catalyze atom-transfer radical addition (ATRA) reactions between bromomalonate and alkenes. This finding paves the way for the design and application of the new type of heavy atom-free organic chromophores for photocatalysis.

| S-EPMC8655941 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data