A C4N4 Diaminopyrimidine Fluorophore |
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Authors: | Dr Hidetoshi Noda Yasuko Asada Dr Tatsuro Maruyama Dr Naoki Takizawa Dr Nobuo N Noda Prof Dr Masakatsu Shibasaki Dr Naoya Kumagai |
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Institution: | Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021 Japan |
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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. |
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Keywords: | bioconjugation fluorescence live-cell imaging pyrimidine Stokes shift |
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