Amphiprotism-coupled near-infrared emission in extended pyrazinacenes containing seven linearly fused pyrazine units

Gary J. Richards, Ael Cador, Shinji Yamada, Anna Middleton, Whitney A. Webre, Jan Labuta, Paul A. Karr, Katsuhiko Ariga, Francis D’Souza, Samia Kahlal, Jean Francois Halet, Jonathan P. Hill

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Peripherally substituted tetradecaazaheptacene (N14Hp) compounds, exhibiting amphiprotism-coupled emission, have been synthesized. X-ray crystallography reveals a planar acene-like chromophore, and electronic absorption and emission occur in the near-infrared biological transparency window (650–900 nm). The compounds exhibit long-wavelength emission with photoluminescence quantum yields ΦPL up to ∼0.61 at 686 nm, with the monodeprotonated state ΦPL ≈ 0.58 at 712 nm. This unprecedented highly nitrogenous chromophore illustrates the stability and utility of the pyrazinacenes for different applications based on their photophysical properties and chemical structures.

Original languageEnglish
Pages (from-to)19570-19574
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number50
DOIs
Publication statusPublished - 2019 Dec 18
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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