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Acid/base-controllable fluorescent molecular switches based on cryptands and basic N-heteroaromatics.

Ming Cheng1, Jing Zhang, Xintong Ren

  • 1Key Laboratory of Mesoscopic Chemistry of MOE, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. China. jjl@nju.edu.cn lywang@nju.edu.cn.

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New fluorescent cryptands (BMP32C10) were synthesized and formed self-assemblies with N-heteroaromatic guests. These host-guest complexes exhibit switchable fluorescence, controlled by acid-base addition.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Fluorescent molecular recognition is crucial for sensing applications.
  • Cryptands offer unique host-guest complexation capabilities.
  • Designing switchable fluorescent systems remains a challenge.

Purpose of the Study:

  • To develop novel fluorescent BMP32C10-based cryptands.
  • To investigate self-assembly formation with N-heteroaromatic guests.
  • To explore acid-base switchable host-guest complexation and fluorescence.

Main Methods:

  • Synthesis of two distinct BMP32C10-based cryptands with binaphthol and coumarin moieties.
  • Formation of self-assemblies with basic N-heteroaromatic guests.
  • Monitoring host-guest complexation and fluorescence changes via acid-base titration.

Main Results:

  • Successful synthesis of fluorescent cryptands 1 and 2.
  • Formation of novel self-assemblies between cryptands and guests.
  • Demonstration of reversible host-guest complexation and fluorescence switching using acid/base stimuli.

Conclusions:

  • BMP32C10-based cryptands can form functional self-assemblies.
  • The developed systems exhibit controllable fluorescence via external stimuli.
  • These findings pave the way for new fluorescent sensors and switches.