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Azulene-Based BN-Heteroaromatics.

Hanshen Xin1, Jing Li1, Xiaodi Yang2

  • 1Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

The Journal of Organic Chemistry
|September 25, 2019
PubMed
Summary

Researchers developed novel azulene-based boron-nitrogen (BN)-heteroaromatics, Az-BN-1 and Az-BN-2. These compounds exhibit unique optical properties and undergo unexpected deboronization, offering new possibilities in materials science.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Azulene is a nonalternant bicyclic aromatic hydrocarbon with unique properties.
  • Azulene is a promising building block for novel polycyclic aromatic hydrocarbons (PAHs) and heteroaromatics.
  • Boron-nitrogen (BN)-embedded heteroaromatics are of significant interest.

Purpose of the Study:

  • To synthesize and characterize the first two azulene-based BN-heteroaromatics, Az-BN-1 and Az-BN-2.
  • To investigate the chemical structures, optical, and electrochemical properties of Az-BN-1 and Az-BN-2.
  • To evaluate the sensing behavior of these compounds towards fluoride ion.

Main Methods:

  • Synthesis of novel azulene-based BN-heteroaromatics.
  • Spectroscopic analysis (UV-Vis, fluorescence) for photophysical properties.
  • Electrochemical measurements (cyclic voltammetry).
  • Sensing studies with fluoride ion and trifluoroacetic acid.

Main Results:

  • Az-BN-1 and Az-BN-2 were successfully synthesized.
  • These compounds display distinct photophysical properties, including lower band gaps and unusual fluorescence compared to other BN-embedded PAHs.
  • Unexpected deboronization of Az-BN-1 and Az-BN-2 was observed upon addition of trifluoroacetic acid.

Conclusions:

  • Azulene-based BN-heteroaromatics possess unique photophysical properties.
  • The observed deboronization is a novel characteristic attributed to the azulene unit.
  • These findings open new avenues for designing advanced BN-heteroaromatic materials.