Related Experiment Video
Updated: Jan 18, 2026
14:11
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
6.7K
Synthesis and Optical Properties of Unsymmetric Aromatically π-Extended BODIPY
Metodej Dvoracek1, Craig Newman1, Mikhail Drobizhev2
1School of Chemical and Biopharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, Dublin D07 EWV4, Ireland.
The Journal of Organic Chemistry
|September 9, 2025
Summary
New BODIPY dyes with fused rings were synthesized. These dyes exhibit strong red fluorescence and enhanced two-photon absorption, showing potential for near-infrared applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Boron-dipyrromethene (BODIPY) dyes are known for their photophysical properties.
- Expanding the π-conjugated system of BODIPY dyes can tune their optical characteristics.
- Fused aromatic systems offer unique structural and electronic properties.
Purpose of the Study:
- To synthesize novel unsymmetrically substituted BODIPY dyes with fused benzo- or naphtho-fragments.
- To optimize the synthetic route for improved yields and reduced byproducts.
- To investigate the photophysical and two-photon absorption (2PA) properties of these extended BODIPY scaffolds.
Main Methods:
- Modular synthesis involving condensation of formylpyrroles with alkylpyrroles.
- Spectroscopic characterization (fluorescence emission, quantum yield determination).
- Experimental and computational studies of two-photon absorption (2PA) properties.
Main Results:
- Successful synthesis of benzo- and naphtho-fused BODIPY dyes.
- Intense red fluorescence observed with emission maxima between 590-680 nm.
- Fluorescence quantum yields ranged from 0.27 to 0.84.
- Two-photon absorption cross-section increased with π-conjugation size, reaching 80 GM for naphthoBODIPY.
Conclusions:
- Developed a modular synthetic strategy for π-extended BODIPY dyes.
- Demonstrated that fused benzo- and naphtho-fragments enhance fluorescence and 2PA properties.
- These novel BODIPY derivatives show promise as near-infrared (NIR) fluorophores with significant nonlinear optical capabilities.
More Related Videos
Related Concept Videos
01:29UV–Vis Spectroscopy: Woodward–Fieser Rules
28.2K
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
28.2K
01:14π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
1.8K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.8K
01:24π Molecular Orbitals of 1,3-Butadiene
11.4K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
11.4K
01:18Aromatic Hydrocarbon Cations: Structural Overview
3.6K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
Removing one hydrogen from the intervening CH2 group...
3.6K
01:18Frost Circles for Different Conjugated Systems
3.6K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.6K
01:18Aromatic Hydrocarbon Anions: Structural Overview
3.5K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
3.5K