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Multi-purpose barbituric acid derivatives with aggregation induced emission.

Hanjun Zhang1, Yuezhi Cui1, Furong Tao1

  • 1School of Chemical and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China.

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
|July 10, 2019
PubMed
Summary

New D-π-A barbituric acid derivatives show promising aggregate induced emission (AIE) and mechanochromic properties. CB-1 and CB-3 demonstrate excellent fluorescence stability for detecting nitroaromatic explosives in water.

Keywords:
Aggregation induced emission (AIE)Fluorescent sensorIntramolecular charge transfer (ICT)Mechanochromic fluorescence (MCF)

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Intramolecular charge transfer (ICT) plays a crucial role in designing functional organic materials.
  • Aggregate induced emission (AIE) and mechanochromism are desirable properties for advanced optical applications.
  • Barbituric acid derivatives offer a versatile scaffold for developing novel optoelectronic materials.

Purpose of the Study:

  • To synthesize and characterize novel D-π-A barbituric acid derivatives.
  • To investigate their aggregate induced emission (AIE) and mechanochromic fluorescent properties.
  • To evaluate their potential for detecting nitroaromatic explosives.

Main Methods:

  • Synthesis of three D-π-A barbituric acid derivatives.
  • Molecular dynamics simulations to understand structure-property relationships.
  • Spectroscopic analysis to assess fluorescence properties and stability.
  • Evaluation of sensing capabilities for nitroaromatic explosives.

Main Results:

  • Successfully synthesized three D-π-A barbituric acid derivatives with ICT mechanisms.
  • CB-1 exhibited superior AIE activity due to favorable molecular conformation and electrostatic interactions.
  • The derivatives displayed mechanochromic fluorescent properties.
  • CB-1 and CB-3 showed enhanced fluorescence stability in aggregated states.
  • High Stern-Volmer quenching constants (Ksv) for CB-1 (6.6 × 10⁴ M⁻¹) and CB-3 (1 × 10⁵ M⁻¹) indicate efficient sensing of nitroaromatic explosives.

Conclusions:

  • The synthesized barbituric acid derivatives possess significant AIE and mechanochromic characteristics.
  • Molecular dynamics simulations provided insights into the AIE mechanism of CB-1.
  • CB-1 and CB-3 are promising candidates for developing sensitive and stable fluorescent sensors for nitroaromatic explosives in aqueous environments.