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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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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Synthesis, Cellular Delivery and In vivo Application of Dendrimer-based pH Sensors
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NIR Absorbing AzaBODIPY Dyes for pH Sensing.

Gugu Kubheka1, John Mack1, Tebello Nyokong1

  • 1Institute for Nanotechnology Innovation, Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa.

Molecules (Basel, Switzerland)
|August 23, 2020
PubMed
Summary
This summary is machine-generated.

Synthesized azaBODIPY dyes 2a and 2b exhibit tunable near-infrared absorption. Their pH sensing capabilities were investigated, revealing potential as colorimetric indicators in acidic conditions.

Keywords:
aza-BODIPY dyeintramolecular charge transferpH sensingpKa valuesphotophysical properties

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Area of Science:

  • Organic Chemistry
  • Photophysics
  • Materials Science

Background:

  • Near-infrared (NIR) absorbing dyes are crucial for various applications.
  • AzaBODIPY dyes offer unique photophysical properties.
  • Understanding substituent effects is key to tuning dye performance.

Purpose of the Study:

  • Synthesize and characterize two novel NIR-absorbing di(thien-2-yl)-di(dimethylanilino)azaBODIPY dyes (2a and 2b).
  • Investigate the impact of dimethylaniline substituent positions on spectral and photophysical properties.
  • Evaluate the pH sensing capabilities of these azaBODIPY dyes.

Main Methods:

  • Organic synthesis of azaBODIPY dyes 2a and 2b.
  • Spectroscopic characterization (UV-Vis absorption, fluorescence).
  • Time-dependent density functional theory (TD-DFT) calculations.
  • pH-dependent studies to determine pKa values.

Main Results:

  • Dyes 2a and 2b exhibit main spectral bands at 824 nm and 790 nm, respectively.
  • Protonation causes a blue-shift in absorption bands (to 696 nm and 730 nm) and a NIR fluorescence 'turn-on' effect.
  • pKa values were determined: ~6.9 and ~7.3 for non-protonated forms, and ~1.4 for monoprotonated forms.

Conclusions:

  • Substituent position significantly influences the photophysical properties of azaBODIPY dyes.
  • The synthesized dyes demonstrate potential as colorimetric pH indicators, particularly under highly acidic conditions.
  • The observed fluorescence 'turn-on' upon protonation is a key feature for sensing applications.