Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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 ?-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.

SUBMITTER: Savoldelli A

PROVIDER: S-EPMC6693341 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Savoldelli Andrea A Meng Qianli Q Paolesse Roberto R Fronczek Frank R FR Smith Kevin M KM Vicente M Graça H MGH

The Journal of organic chemistry 20180529 12

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 fluor ...[more]

PMID: 29774744

Similar Datasets

Thieno-pyrrole-fused BODIPY intermediate as a platform to multifunctional NIR agents.

Project description:We report the synthesis, photophysical and electrochemical properties, and in vivo fluorescence imaging of a series of new thieno-pyrrole-fused near-infrared (NIR) BODIPY agents by using a versatile intermediate as a building block. The versatile thieno-pyrrole-fused BODIPY intermediate was rationally designed to bear bromo-substituents and absorb in the mid-red region (635 nm) to act as an organic electrophile for the development of NIR multifunctional agents. The use of subsequent palladium-catalyzed and nucleophilic substitution reactions afforded highly conjugated NIR BODIPYs. The novel BODIPYs exhibit long-wavelength absorptions in the NIR region (650-840 nm). The agents produce sharp fluorescence bands, and most of them display respectable quantum yields of fluorescence (0.05-0.87) useful for biomedical imaging, as demonstrated by in vivo imaging with SBDPiR740. Interestingly, a number of agents in the series that are non-halogenated were reactive to O2 at the triplet photo-excited state coupled with a favorable redox potential and decent fluorescence, and hence could be potential candidates for use as photosensitizers in fluorescence-guided photodynamic therapy. Furthermore, the synthetic approach allows further functionalization of the highly conjugated NIR BODIPYs to tune the excited states (PET, ICT) and to conjugate targeting moieties for enhanced biological applications.

| S-EPMC7323977 | biostudies-literature

Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.

Project description:An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2-5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.

| S-EPMC4881425 | biostudies-literature

Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives.

Project description:The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel-Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformational studies including Density Functional Theory (DFT) modelling were performed. The relative stability of ortho-quinone methides (o-QMs) was calculated, the geometries obtained were compared with the experimentally determined NMR structures, and thereby, the regioselectivity of the reactions has been assigned.

| S-EPMC7321197 | biostudies-literature

Regioselective synthesis, characterization, and antimicrobial activities of some new monosaccharide derivatives.

Project description:A regioselective acylation series of methyl ?-D-glucopyranoside (1), methyl 3-O-benzoyl-4,6-O-benzylidene-?-D-mannopyranoside (1A), and methyl 4,6-O-benzylidene-2-O-(3,5-dinitrobenzoyl)-?-D-mannopyranoside (1B) has been carried out by the direct acylation method and afforded the 2,6-di-O-glucopyranoside and 2 or 3-O-mannopyranoside derivatives in an excellent yield. In order to obtain newer products, the 2,6-di-O-glucopyranoside derivative was further transformed to a series of 3,4-di-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated on the basis of IR, (1)H-NMR, (13)C-NMR, (13)C-DEPT spectral data, and elemental analysis. These synthesized derivatives were screened for in vitro antimicrobial activities against ten human pathogenic and five phytopathogenic microorganisms. A number of test compounds showed remarkable antimicrobial activity comparable to, and in some cases even higher than, the standard antibiotics employed. It was observed that methyl 3,4-di-O-(3-chlorobenzoyl)-2,6-di-O-hexanoyl-?-D-glucopyranoside (8) exhibited a varied range of MIC from 12.5 ?g/disc to 25 ?g/disc by the disk diffusion method and 1000 ?g/mL to 1250 ?g/mL by the broth macrodilution method.

| S-EPMC3951222 | biostudies-literature

Regioselective synthesis of water-soluble monophosphate derivatives of combretastatin A-1.

Project description:The natural products combretastatin A-4 (CA4) and combretastatin A-1 (CA1) are potent cancer vascular disrupting agents and inhibitors of tubulin assembly (IC?? = 1-2 ?M). The phosphorylated prodrugs CA4P and CA1P are undergoing human clinical trials against cancer. CA1 is unique due to its incorporation of a vicinal phenol, which has afforded the opportunity to prepare both diphosphate and regioisomeric monophosphate derivatives. Here, we describe the first synthetic routes suitable for the regiospecific preparation of the CA1-monophosphates CA1MPA (8a/b) and CA1MPB (4a/b). The essential regiochemistry necessary to distinguish between the two vicinal phenolic groups was accomplished with a tosyl protecting group strategy. Each of the four monophosphate analogues (including Z and E isomers) demonstrated in vitro cytotoxicity against selected human cancer cell lines comparable to their corresponding diphosphate congeners. Furthermore, Z-CA1MPA (8a) and Z-CA1MPB (4a) were inactive as inhibitors of tubulin assembly (IC?? > 40 ?M), as anticipated in this pure protein assay.

| S-EPMC3275140 | biostudies-literature

Synthesis, Structure and Antioxidant Activity of Cyclohexene-Fused Selenuranes and Related Derivatives.

Project description:Synthesis, structure and antioxidant activity of new cyclohexene-fused spiroselenuranes and a spirotellurane is reported. Oxidation reactions of bis(o-formylcyclohex- 1-ene)selenide/bis(2-hydroxymethylcyclohex-1-ene)selenide provide the corresponding spiroselenuranes. The glutathione peroxidase-like activity of the newly synthesized compounds has been evaluated.

| S-EPMC6332442 | biostudies-literature

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells.

Project description:We report two novel functional dyes based on a boron-dipyrromethene (BODIPY) core displaying a panchromatic absorption with an extension to the near-infrared (NIR) range. An innovative synthetic approach for preparing the 2,3,5,6-tetramethyl-BODIPY unit is disclosed, and a versatile way to further functionalize this unit has been developed. The optoelectronic properties of the two dyes were computed by density functional theory modelling (DFT) and characterized through UV-vis spectroscopy and cyclic voltammetry (CV) measurements. Finally, we report preliminary results obtained using these functional dyes as photosensitizers in dye-sensitized solar cells (DSSCs).

| S-EPMC6664387 | biostudies-literature

Synthesis, Photophysics, Electrochemistry and Electrogenerated Chemiluminescence of a Homologous Set of BODIPY-Appended Bipyridine Derivatives.

Project description:Two new 2,2'-bipyridine (bpy) based ligands with ancillary BODIPY chromophores attached at the 4 and 4'-positions were prepared and characterized, which vary in the substitution pattern about the BODIPY periphery by either excluding (BB1) or including (BB2) a ?-alkyl substituent. Both absorb strongly throughout the visible region and are strongly emissive. The basic photophysics and electrochemical properties of BB1 and BB2 are comparable to those of the BODIPY monomers on which they are based. The solid-state structures and electronic structure calculations both indicate that there is negligible electronic communication between the BODIPY moieties and the intervening bpy spacers. Electrogenerated chemiluminescence spectra of the two Bpy-BODIPY derivatives are similar to their recorded fluorescence profiles and are strongly influenced by substituents on the BODIPY chromophores. These 2,2'-bipyridine derivatives represent a new set of ligands that should find utility in applications including light-harvesting, photocatalysis, and molecular electronics.

| S-EPMC3505096 | biostudies-literature

A general and highly regioselective synthesis approach to multi-functionalized organoimido derivatives of Polyoxometalates.

Project description:Organoimidoylization of Polyoxometalates (POMs) can dramatically modify the electronic structures of POMs and gives rise to novel "value-adding" properties of the POMs for promising material applications including photo-electronic transformation and catalysis. To date, the preparation of multi-functionalized organoimido derivatives of POMs is generally conducted under strict condition and is time-consuming with limited yields. Herein, a series of regioselective polyorganoimido derivatives of POMs, ocatant- [Mo6O13(NAr)3(μ2-NAr)3](2-) (Ar = phenyl (1), p-methoxyphenyl (2) and p-ethylphenyl (3)), were synthesized with high selectivity and in good yields via a general and highly regioselective synthesis method, called as the one-octant synthesis protocol. The reaction was monitored by ESI-MS and the as-prepared products were studied by ESI-MS, IR, UV-Vis, EA, (1)HNMR, single crystal XRD analysis and DFT calculations. The one-octant synthesis protocol here may serve as an idea method to design novel nanoscale POM-based organic-inorganic multi-functional hybrids.

| S-EPMC4842987 | biostudies-literature

Photolysis of the BODIPY dye activated by pillar[5]arene.

Project description:Here, a pseudo[3]rotaxane comprising a fluorescent BODIPY derivative and pillar[5]arene was conveniently fabricated via host-guest complexation. Importantly, in this system, the efficient photodecomposition of the BODIPY derivative in the presence of pillar[5]arene was witnessed upon irradiation at 311 nm light, which was demonstrated via UV-Vis absorption, fluorescence emission, NMR and HR-MS spectroscopy techniques, but the only BODIPY dye in the absence of pillar[5]arene couldn't undergo photodegradation. We demonstrated that pillar[5]arene could act as an activator to trigger the photodegradation reaction of BODIPY derivatives via free radical reactions even without supramolecular interactions. The present results provide a new strategy for the efficient photolysis of organic dyes.

| S-EPMC8694983 | 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