Related Experiment Video
Updated: Jun 17, 2026
14:11
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Highly fluorescent BODIPY dyes modulated with spirofluorene moieties.
Toshiyuki Kowada1, Shuhei Yamaguchi, Kouichi Ohe
1Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Organic Letters
|December 17, 2009
Summary
Researchers synthesized novel, rigid BODIPY dyes with spirofluorene. These dyes show strong, red-shifted fluorescence and controllable ON/OFF switching, useful for advanced optical applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Boron-dipyrromethene (BODIPY) dyes are widely used due to their photophysical properties.
- Structural rigidity can enhance fluorescence quantum yields and photostability.
- Spirocyclic structures offer unique conformational constraints.
Purpose of the Study:
- To synthesize novel structurally rigid BODIPY dyes incorporating spirofluorene moieties.
- To investigate the photophysical properties, particularly fluorescence, of these new compounds.
- To explore the solvent-dependent fluorescence switching behavior of a related amino-BODIPY dye.
Main Methods:
- Synthesis of BODIPY derivatives featuring spirofluorene units.
- Spectroscopic characterization (absorption, emission) of the synthesized dyes.
- Fluorescence ON/OFF switching studies in various solvents.
Main Results:
- Successful synthesis of structurally rigid BODIPY dyes with spirofluorene.
- Observation of intense bathochromic (red-shifted) fluorescence.
- Demonstration of solvent-dependent fluorescence ON/OFF switching in an amino-BODIPY derivative.
Conclusions:
- Structurally constrained BODIPY dyes with spirofluorene exhibit enhanced fluorescence properties.
- The incorporation of spirofluorene moieties leads to significant changes in photophysical behavior.
- BODIPY dyes with specific functional groups can display environmentally sensitive fluorescence switching.
Related Concept Videos
01:19Protein Dynamics in Living Cells
Different fluorescence-based techniques are used to study the protein dynamics in living cells. These techniques include FRAP, FRET, and PET.
Fluorescent recovery after photobleaching (FRAP) is a fluorescent-protein-based detection technique used to quantify protein movement rates within the cell. This method exposes a small portion of the cell to an intense laser beam. The laser beam causes permanent photobleaching of the fluorophore-tagged proteins in the exposed region. As the bleached...
Fluorescent recovery after photobleaching (FRAP) is a fluorescent-protein-based detection technique used to quantify protein movement rates within the cell. This method exposes a small portion of the cell to an intense laser beam. The laser beam causes permanent photobleaching of the fluorophore-tagged proteins in the exposed region. As the bleached...
03:31Labeling DNA Probes
DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
Radioisotopes, fluorophores, or small molecule binding partners like biotin or digoxigenin, are the most widely used reporter tags for labeling DNA probes. These labels can be attached to the probe DNA molecule via...
Radioisotopes, fluorophores, or small molecule binding partners like biotin or digoxigenin, are the most widely used reporter tags for labeling DNA probes. These labels can be attached to the probe DNA molecule via...
01:26Variables Affecting Phosphorescence and Fluorescence
Fluorescence and phosphorescence are essential phenomena in fields like analytical chemistry, biological imaging, and materials science, where they detect molecular properties and visualize cellular structures. Understanding the variables that influence these luminescent behaviors is crucial for maximizing accuracy and efficiency in their applications. These variables can broadly be grouped into chemical structure, solvent properties, and external conditions, each playing a distinct role in...
01:37Super-resolution Fluorescence Microscopy
Super-resolution fluorescence microscopy (SRFM) provides a better resolution than conventional fluorescence microscopy by reducing the point spread function (PSF). PSF is the light intensity distribution from a point that causes it to appear blurred. Due to PSF, each fluorescing point appears bigger than its actual size, and it is the PSF interference of nearby fluorophores that causes the blurred image. Various approaches to achieving higher resolution through SRFM have recently been developed.