A C4N4 Diaminopyrimidine Fluorophore

Hidetoshi Noda, Yasuko Asada, Tatsuro Maruyama, Naoki Takizawa, Nobuo N. Noda, Masakatsu Shibasaki, Naoya Kumagai

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A new scaffold for producing efficient organic fluorescent materials was identified: 2,5-diamino-4,6-diarylpyrimidine featuring a C4N4 elemental composition. Single-step installation of two aryl groups at the 4,6-positions of the pyrimidine core delivered fluorescent organic materials in a modular fashion. A range of fluorescent compounds with distinct absorption/emission properties was readily accessed by changing the aromatic attachments. A generally high absorption coefficient and quantum yield were observed, including C4N4 derivatives that could fluoresce even in the solid state. The two amino groups at the 2,5-positions of the pyrimidine were essential for intense fluorescence with a large Stokes shift, which was corroborated by structural relaxation to a p-iminoquinone-like structure in the excited state. Besides live-cell imaging capabilities, fluorescent labeling of a protein involved in autophagy elucidated a new protein–protein interaction, supporting potential utility in bioimaging applications.

Original languageEnglish
Pages (from-to)4299-4304
Number of pages6
JournalChemistry - A European Journal
Volume25
Issue number17
DOIs
Publication statusPublished - 2019 Mar 21
Externally publishedYes

Keywords

  • bioconjugation
  • fluorescence
  • live-cell imaging
  • pyrimidine
  • Stokes shift

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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