We report a boron dipyrromethene that is chiral at boron and carbon (B*C*-BODIPY) and accessible through a two-pot, one-step synthesis-an interrupted Knoevenagel condensation. The electronic circular dichroism spectra of chiral high performance liquid chromatography-resolved enantiomers show clear Cotton effects (∣∣ ∼ 2.0 × 10) in the visible region, suggesting efficient chirality induction to the otherwise achiral BODIPY. The dye's unusually weak fluorescence ( < 0.01) is attributed partly to vibrational relaxations, as revealed by viscosity experiments, and partly to probable intersystem crossing that may be facilitated by the reduced symmetry of the bent-shaped molecular geometry.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d2cc02179j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Degradable Theranostic Polyurethane for Macrophage-Targeted Antileishmanial Drug Delivery.
Biomacromolecules
January 2025
Polymer Research Centre and Centre for Advanced Functional Materials, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Nadia, Mohanpur 741246, West Bengal, India.
The present investigation aims to develop a reactive oxygen species (ROS) and esterase-responsive biodegradable mannosylated polyurethane to effectively deliver the encapsulated antileishmanial drug amphotericin B (AmB) selectively to infected macrophage cells. Owing to suitable amphiphilic balance, the as-synthesized glycosylated polyurethane () with aryl boronic ester-based diol () moiety as ROS-trigger, water-soluble mannose pendants, and fluorescent 4,4-difluoro-4-bora-3a,4a-diaza--indacene (BODIPY) chain ends for bioimaging formed nanoaggregates in an aqueous medium as confirmed by H NMR spectroscopy, dynamic light scattering (DLS), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), and critical aggregation concentration (CAC) measurements. Aided by two endogenous stimuli present in phagolysosome, ROS and esterase, AmB-encapsulated polymeric nanoaggregates as drug delivery vehicles achieved an efficient reduction of both and intracellular amastigote burden compared to the free AmB.
View Article and Find Full Text PDFRecent advances in the development of enantiopure BODIPYs and some related enantiomeric compounds.
Chem Commun (Camb)
January 2025
Department of Chemistry, Khalifa University, SAN Campus, Abu Dhabi, United Arab Emirates.
During the process of developing smart chiroptical luminophores, small chiral organic dyes have emerged as candidates of utmost importance. In this regard, the chiral variants of boron dipyrromethene (BODIPY) serve as suitable molecules owing to their excellent photophysical properties such as high fluorescence quantum yields, narrow emission bandwidths with high peak intensities, high photo and chemical stability, and higher molar extinction coefficients. Thus, the last decade observed an influx of research from various research groups for the induction of chirality in originally achiral BODIPY.
View Article and Find Full Text PDFPlasmon-Enhanced Fluorescence Based on Gold Nanobipyramids with PEG-Controlled Distance for Near-Infrared and Visual Analysis of Amyloid-β Aggregation.
ACS Appl Mater Interfaces
January 2025
College of Food and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023, PR China.
The number of cases of Alzheimer's disease (AD) characterized by progressive amnestic syndrome is dramatically increased with population aging. It is urgent to detect and diagnose this disease early. The state of amyloid-beta protein 1-42 (Aβ) was commonly regarded as a hallmark for early diagnosis of AD.
View Article and Find Full Text PDFDirect Synthesis of Topology-Controlled BODIPY and CO2-Based Zirconium Metal-Organic Frameworks for Efficient Photocatalytic CO2 Reduction.
Angew Chem Int Ed Engl
January 2025
National University of Singapore, Department of Chemical and Biomolecular Engineering, 4 Engineering Drive 4, National University of Singapore, 117585, Singapore, SINGAPORE.
Boron dipyrromethene (BODIPY)-based zirconium metal-organic frameworks (Zr-MOFs) possess strong light-harvesting capabilities and great potential for artificial photosynthesis without the use of sacrificial reagents. However, their direct preparation has not yet been achieved due to challenges in synthesizing suitable ligands. Herein, we reported the first successful direct synthesis of BODIPY-based Zr-MOFs, utilizing CO₂ as a feedstock.
View Article and Find Full Text PDFInteraction of Vitamin D-BODIPY With Fat Cells and the Link to Obesity-associated Vitamin D Deficiency.
Anticancer Res
January 2025
Section of Endocrinology, Diabetes, Nutrition and Weight Management, Department of Medicine, Boston University Chobanian & Avedisian School of Medicine, Boston, MA, U.S.A.;
Background/aim: Obese individuals often exhibit vitamin D deficiency, potentially due to sequestration in fat cells. Little is known about how vitamin D enters adipocytes and associates with the intracellular lipid droplet.
Materials And Methods: Newly differentiated human and mouse (3T3-L1) adipocytes and primary mouse adipocytes were treated with vitamin D covalently linked to green fluorescent BODIPY (VitD-B) or Green BODIPY (GB) as control.
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!