TY - JOUR
T1 - A C4N4 Diaminopyrimidine Fluorophore
AU - Noda, Hidetoshi
AU - Asada, Yasuko
AU - Maruyama, Tatsuro
AU - Takizawa, Naoki
AU - Noda, Nobuo N.
AU - Shibasaki, Masakatsu
AU - Kumagai, Naoya
N1 - Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/3/21
Y1 - 2019/3/21
N2 - 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.
AB - 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.
KW - Stokes shift
KW - bioconjugation
KW - fluorescence
KW - live-cell imaging
KW - pyrimidine
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U2 - 10.1002/chem.201900467
DO - 10.1002/chem.201900467
M3 - Article
C2 - 30714234
AN - SCOPUS:85061937702
SN - 0947-6539
VL - 25
SP - 4299
EP - 4304
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 17
ER -