Solid-State Emissive Pillar[6]arene Derivative Having Alternate Methylene and Nitrogen Bridges.

Chem Asian J

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.

Published: May 2024

AI Article Synopsis

  • Macrocyclic arenes can adapt their shape to form complexes with specific guest molecules, but tend to have poor light emission in solid form due to self-absorption issues.* -
  • New derivatives of pillar[6]arene were synthesized, featuring a structure that alternates between methylene and nitrogen bridges, enhancing their light-emission properties by improving charge transfer dynamics.* -
  • One of these new nitrogen-containing pillar[6]arenes exhibits a high photoluminescence quantum yield and can detect nitrobenzene vapor through a fluorescence quenching effect, forming non-emissive complexes upon exposure.*

Article Abstract

Macrocyclic arenes show conformational adaptability, which allows host-guest complexations with the size-matched guest molecules. However, their emission properties are often poor in the solid states due to the self-absorption. Herein, we newly synthesized pillar[6]arene derivatives having alternate methylene and nitrogen bridging structures. Solvatochromic study reveals that the nitrogen-embedding into the cyclic structures can strengthen the intramolecular charge transfer (CT) nature compared to that of the linear nitrogen-bridged precursor. Owing to the large Stokes shift in the solid state, one of the nitrogen-embedded pillar[6]arenes shows high absolute photoluminescence quantum yield (Φ=0.36). Furthermore, it displays a turn-off sensing ability toward nitrobenzene (NB) vapor; a fluorescence quenching is observed when exposed to the NB vapor. From the structural analysis before and after the exposure of NB vapor, the amorphous nitrogen-embedded pillar[6]arene efficiently co-crystallize with NB and formed non-emissive intermolecular CT complexes with NB.

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Source
http://dx.doi.org/10.1002/asia.202400106DOI Listing

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