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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
09:44

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Published on: October 15, 2019

"Clickable" pillar[5]arenes.

Tomoki Ogoshi1, Ryohei Shiga, Masayoshi Hashizume

  • 1Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. ogoshi@t.kanazawa-u.ac.jp

Chemical Communications (Cambridge, England)
|May 24, 2011
PubMed
Summary
This summary is machine-generated.

Bulky benzyl and pyrenyl groups attached to pillar[5]arene via click reactions restricted molecular rotation. The perpyrenylated pillar[5]arene exhibited thermally-responsive excimer emission, unlike its unit model.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Pillar[5]arenes are macrocyclic hosts with tunable properties.
  • Controlling molecular rotation is key for developing responsive materials.
  • Click reactions offer efficient methods for functionalizing macrocycles.

Purpose of the Study:

  • To investigate the impact of bulky substituents on pillar[5]arene rotation.
  • To explore the photophysical properties of functionalized pillar[5]arenes.
  • To determine the origin of thermally-responsive emission in perpyrenylated pillar[5]arene.

Main Methods:

  • Synthesis of pillar[5]arene derivatives using click chemistry.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Analysis of photophysical properties, including fluorescence spectroscopy.

Main Results:

  • Bulky benzyl and pyrenyl groups significantly inhibited or slowed molecular rotation on the NMR chemical shift timescale.
  • The perpyrenylated pillar[5]arene displayed a thermally-responsive excimer emission.
  • A unit model lacking the complete macrocyclic structure did not show this thermal response.

Conclusions:

  • Steric hindrance from bulky substituents effectively controls molecular dynamics in pillar[5]arenes.
  • The observed thermally-responsive excimer emission is an emergent property of the intact perpyrenylated pillar[5]arene macrocycle.
  • This study provides insights into designing functional supramolecular materials with tunable photophysical properties.