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A New Water‐Soluble Phosphorus‐Dipyrromethene and Phosphorus‐Azadipyrromethene Dye: PODIPY/aza‐PODIPY
Author(s) -
Jiang XinDong,
Zhao Jiuli,
Xi Dongmei,
Yu Haifeng,
Guan Jian,
Li Shuang,
Sun ChangLiang,
Xiao LinJiu
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406535
Subject(s) - homo/lumo , phosphorus , chemistry , absorption (acoustics) , bodipy , photochemistry , molecule , materials science , organic chemistry , fluorescence , optics , physics , composite material
PODIPY and aza‐PODIPY have been successfully prepared by the treatment of dipyrromethene and azadipyrromethene with POCl 3 in the presence of Et 3 N. The new PODIPY and aza‐PODIPY dyes are found to have photophysical properties. PODIPY and aza‐PODIPY are water‐soluble, and aza‐PODIPY is suited for labeling living Hep‐2 cells for imaging assays in the near‐infrared region. Molecular orbital calculations show that the increase in the HOMO–LUMO band gap for the lowest energy absorption bands is observed in the new phosphorus‐containing aza‐PODIPY, and the HOMO and LUMO energies of aza‐PODIPY are found to be higher than those of aza‐BODIPY.