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Turning Non-Emissive Schiff Bases Into Aggregate Emitters

  • Xinmeng Chen
  • , Siwei Zhang
  • , Yefei Jiang
  • , Guiying He
  • , Minjie Zhang
  • , Jin Wang
  • , Zihao Deng
  • , Haoran Wang
  • , Jacky W.Y. Lam*
  • , Lianrui Hu*
  • , Ben Zhong Tang*
  • *Corresponding author for this work
  • Department of Chemistry
  • Hong Kong University of Science and Technology
  • Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development
  • East China Normal University
  • Photonics Initiative
  • City University of New York
  • School of Science and Engineering
  • Chinese University of Hong Kong

Research output: Contribution to journal › Article › peer-review

Abstract

Schiff bases are a crucial component in various functional materials but often exhibit non-emissive behavior which significantly limits their potential applications as luminescent materials. However, traditional approaches to convert them into aggregate emitters often require intricate molecular design, tedious synthesis, and significant time and resource consumption. Herein, we present a cocrystallization-induced emission strategy that can transform non-emissive (hetero)aryl-substituted Schiff bases into green-yellow to yellow aggregate emitters via even simple grinding of a mixture of Schiff bases and 1,2,4,5-tetracyanobenzene (TCB) mixtures. The combined experimental and theoretical analysis revealed that the cocrystallization inhibits the C=N isomerization and promotes face-to-face π–π interaction, which restricts access to both the dark state and canonical intersection to ultimately induce emission. Furthermore, the induced emission enables the observation of solid-state molecular diffusion through fluorescence signals, advancing white light emission diodes, and notably, solution-processed organic light-emitting diodes based on cocrystal for the first time. This study not only highlights the potential of developing new C=N structural motifs for AIEgens but also could boost advancements in related structure motifs like C=C and N=N.

Original languageEnglish
Article numbere202402175
JournalAngewandte Chemie - International Edition
Volume63
Issue number19
DOIs
StatePublished - 6 May 2024

Keywords

  • Aggregation-Induced Emission
  • Cocrystals
  • Luminescence
  • Schiff bases

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