σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals

Catherine Demangeat, Yixuan Dou, Bin Hu, Yann Bretonnière, Chantal Andraud, Anthony D'Aléo, Jeong Weon Wu, Eunkyoung Kim, Tangui Le Bahers, André Jean Attias

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.

Original languageEnglish
Pages (from-to)2446-2454
Number of pages9
JournalAngewandte Chemie - International Edition
Volume60
Issue number5
DOIs
StatePublished - 1 Feb 2021

Keywords

  • hydrogen bonds
  • molecular crystals
  • organic room-temperature phosphorescence
  • supramolecular self-assembly
  • σ-conjugation

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