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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Emissive Click Cages.

Suman Maji1,2, Jayanta Samanta1,2, Krishanu Samanta1,2

  • 1Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata, 700032, India.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 27, 2023
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Summary
This summary is machine-generated.

Researchers synthesized novel organic cage molecules with aggregation-induced emissive (AIE) properties using click chemistry. These cages show potential for detecting nitroaromatic explosives, including picric acid, with high sensitivity.

Keywords:
aggregation-induced emissionclick reactionexplosive sensingorganic cagespicric acid

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Aggregation-induced emission (AIE) luminogens (AIEgens) are crucial for developing advanced optical materials.
  • Organic cages offer unique structural frameworks for hosting and functionalizing guest molecules.
  • Click chemistry provides efficient and reliable methods for constructing complex molecular architectures.

Purpose of the Study:

  • To synthesize cofacial organic cage molecules incorporating AIEgens.
  • To investigate the influence of AIEgen structure on cage formation and properties.
  • To evaluate the sensing capabilities of the synthesized cages for nitroaromatic explosives.

Main Methods:

  • Four-fold copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) 'click' reactions were employed for cage synthesis.
  • Tetraphenylethylene (TPE) and tetrabiphenylethylene (TBPE) were used as AIEgens.
  • X-ray crystallography was used to determine the structures and chirality of the resulting cages.
  • Spectroscopic methods were used to study the photophysical properties and sensing performance.

Main Results:

  • Two orientational isomers (TPE-CC-1A and TPE-CC-1B) and one isomer (TBPE-CC-2) were successfully synthesized.
  • High yields (>40%) of four-fold click products were achieved.
  • The cages exhibited propeller-shaped chirality influenced by the orientation of phenyl rings.
  • The synthesized cages displayed solution-state emission and enhanced AIE in aqueous media.
  • Turn-off emission sensing of nitroaromatic explosives, with high selectivity for picric acid (25-38 nM detection range), was demonstrated.

Conclusions:

  • Cofacial organic cages incorporating AIEgens can be efficiently synthesized using CuAAC click chemistry.
  • The structural features of the AIEgen influence the isomerism and chirality of the resulting cages.
  • These novel organic cages show promise as sensitive and selective fluorescent sensors for explosive detection.