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Area of Science:

  • Photophysical Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Room-temperature phosphorescence (RTP) is a long-lived emission phenomenon.
  • RTP is observed in proteins and polymers due to through-space electronic communication.
  • Small molecules with intrinsic RTP capabilities and through-space electronic communication are scarce.

Purpose of the Study:

  • To design and investigate a novel small molecule system exhibiting alkyl halide-responsive room-temperature phosphorescence (RTP).
  • To explore the mechanism of through-space charge transfer (TSCT) within a pillararene framework.
  • To understand the structural requirements for achieving RTP in small molecules.

Main Methods:

  • Synthesis of meta-formylphenyl-bearing pillar[5]arene derivatives.
  • Investigation of RTP properties upon treatment with bromoethane (an alkyl halide).
  • Structural analysis using single-crystal X-ray diffraction.
  • Quantum chemical calculations to elucidate electronic structure and photophysical pathways.

Main Results:

  • A meta-formylphenyl-bearing pillar[5]arene derivative demonstrated significant RTP enhancement upon addition of bromoethane.
  • An isomeric para-formylphenyl-bearing pillar[5]arene derivative did not exhibit RTP.
  • Structural and computational analyses revealed that TSCT within the pillararene cavity is crucial for RTP.
  • Key factors influencing TSCT, energy gaps, and intersystem crossing were identified.

Conclusions:

  • The developed pillararene derivative functions as an effective RTP system responsive to alkyl halides.
  • Through-space charge transfer within the pillararene cavity is essential for the observed RTP.
  • This study provides a foundation for designing new small molecules with tunable RTP characteristics.