Conformationally restricted aza-dipyrromethene boron difluorides (aza-BODIPYs) with high fluorescent quantum yields.

Chem Asian J

The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241000 (China).

Published: March 2014

AI Article Synopsis

  • A new method is introduced for creating highly fluorescent near-infrared aza-BODIPY dyes, achieving fluorescence quantum yields as high as 0.81 in toluene.
  • This method relies on limiting the rotation of 1,7-phenyl groups by adding bulky substituents, reducing nonradiative relaxation and enhancing fluorescence.
  • X-ray diffraction studies verify the large torsion angles between the 1,7-phenyl groups and the aza-BODIPY core, confirming the structural changes in these dyes.

Article Abstract

A simple approach to the highly fluorescent near-infrared aza-BODIPY dyes with higher fluorescence quantum yields (up to 0.81 in toluene) in comparison with their known analogues is presented. Our approach is based on the restricted rotations of the 1,7-phenyl groups to the mean plane of the aza-BODIPYs, which is achieved through the installation of bulky substituents on the 1,7-phenyl groups of aza-BODIPYs and results in a reduced nonradiative relaxation process in solution. The large torsion angles between the 1,7-phenyl groups and the aza-BODIPY core (ϕ1 and ϕ2 in these novel conformationally restricted aza-BODIPYs) were confirmed by X-ray diffraction studies.

Download full-text PDF

Source
http://dx.doi.org/10.1002/asia.201301362DOI Listing

Publication Analysis

Top Keywords

17-phenyl groups
12
conformationally restricted
8
quantum yields
8
restricted aza-dipyrromethene
4
aza-dipyrromethene boron
4
boron difluorides
4
aza-bodipys
4
difluorides aza-bodipys
4
aza-bodipys high
4
high fluorescent
4

Similar Publications

Identification of Effector Metabolites Using Exometabolite Profiling of Diverse Microalgae.

mSystems

December 2021

Environmental Genomics and Systems Biology Division, Lawrence Berkeley National Laboratorygrid.184769.5, Berkeley, California, USA.

Dissolved exometabolites mediate algal interactions in aquatic ecosystems, but microalgal exometabolomes remain understudied. We conducted an untargeted metabolomic analysis of nonpolar exometabolites exuded from four phylogenetically and ecologically diverse eukaryotic microalgal strains grown in the laboratory, freshwater Chlamydomonas reinhardtii, brackish sp., marine Phaeodactylum tricornutum, and marine Microchloropsis salina, to identify released metabolites based on relative enrichment in the exometabolomes compared to cell pellet metabolomes.

View Article and Find Full Text PDF

Subclinical mastitis (SCM) is one of the highly infectious diseases in dairy cows with the characteristics of high incidence and nonvisible clinical symptoms. The gastrointestinal microbiota is closely related to mastitis. Inulin is a prebiotic fiber with functions in improving intestinal microbial communities and enhancing the host's immunity.

View Article and Find Full Text PDF

Prostaglandin E2 (PGE2) is involved in numerous physiological and pathological processes of the kidney via its four receptors. A previous study has suggested that a defect in the PGE2 receptor 1 (EP1) gene markedly suppressed the transforming growth factor‑β1 (TGF‑β1)‑induced mesangial cell (MC) proliferation and extracellular matrix aggregation. Therefore, the present study aimed to adopt a pharmacological method of specifically suppressing or activating the EP1 receptor to further verify and demonstrate these results.

View Article and Find Full Text PDF

Synthesis of Oridonin Derivatives via Mizoroki-Heck Reaction and Click Chemistry for Cytotoxic Activity.

Anticancer Agents Med Chem

February 2020

Shanghai Institute for Advanced Immunochemical Studies (SIAIS), Shanghai Tech University, Shanghai, 201210, China.

Background: Natural products (NPs) are evolutionarily chosen "privileged structures" that have a profound impact upon the anticancer drug discovery and development progress. However, the search for new drugs based on structure modification of NPs has often been hindered due to the tedious and complicated synthetic pathways. Fortunately, Mizoroki-Heck reaction and copper-catalyzed alkyne-azide cycloaddition (CuAAC) could provide perfect strategies for selective modification on NPs even in the presence of liable functionalities.

View Article and Find Full Text PDF

Effect of PGE-EP pathway on primary cultured rat neuron injury caused by aluminum.

Oncotarget

November 2017

Department of Pharmacology, Chongqing Medical University, The Key Laboratory of Biochemistry and Molecular Pharmacology, Chongqing 400016, China.

To observe the characteristic changes of PGE-EP pathway and divergent functions of PGE receptor subtypes on neuronal injury. The primary cultured rat hippocampus neuron injury model was established via aluminum maltolate (100 μM). The aluminum-overload neurons were treated with the agonists of EP1 (17-phenyl trinor Prostaglandin E2 ethyl amide), EP2 (Butaprost), EP3 (Sulprostone) and EP4 (CAY10598) and antagonists of EP1 (SC-19220), EP2 (AH6809) and EP4 (L-161982) at different concentrations, respectively.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!