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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Atomic fluorescence spectroscopy (AFS) is an analytical technique that involves the electronic transitions of atoms in a flame, furnace, or plasma being excited by electromagnetic (EM) radiation. When these atoms absorb energy, they become excited and subsequently release energy as they return to their original state. This emitted light, or "fluorescence," is observed at a right angle to the incident beam. Both absorption and emission processes transpire at distinct wavelengths, which...
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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...
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
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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.
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Related Experiment Video

Updated: Nov 17, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Hydroxyaromatic Fluorophores.

Joseph J M Hurley1, Quinton J Meisner1, Chen Huang2

  • 1Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, Florida 32306-4390, United States.

ACS Omega
|February 15, 2021
PubMed
Summary
This summary is machine-generated.

Hydroxyaromatic fluorophores with excited state proton transfer (ESPT) exhibit dual emission. This study clarifies their optical properties and provides tools for predicting their behavior in applications like organic light-emitting diodes (LEDs) and sensors.

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Area of Science:

  • Photochemistry and photophysics
  • Materials chemistry
  • Analytical biochemistry

Background:

  • Hydroxyaromatic compounds are crucial fluorophores in biochemistry and microscopy.
  • Hydroxyaromatic dyes capable of excited state proton transfer (ESPT) show dual emission, attracting interest in materials science and physical chemistry.
  • ESPT compounds are valuable for molecular photophysics and potential applications in organic light-emitting diodes (LEDs) and fluorescent sensors.

Purpose of the Study:

  • To summarize the spectroscopic properties of common hydroxyaromatic dyes.
  • To clarify the optical properties of these compounds, considering proton transfer equilibria.
  • To provide tools for understanding and predicting the photophysical behavior of hydroxyaromatic fluorophores.

Main Methods:

  • Review of literature on hydroxyaromatic dyes and ESPT.
  • Quantum chemical calculations of absorption and emission energies.
  • Analysis of spectroscopic properties in neutral and anionic forms.

Main Results:

  • Proton transfer equilibria significantly influence the absorption and emission properties of hydroxyaromatic dyes.
  • Computational methods aid in understanding the photophysics of these dyes.
  • Spectroscopic data for common hydroxyaromatic fluorophores are presented.

Conclusions:

  • A clearer understanding of hydroxyaromatic fluorophore optical properties is achieved.
  • Quantum chemical calculations are valuable for predicting dye behavior.
  • This work facilitates the rational design of fluorophores for specific applications.