A new water-soluble phosphorus-dipyrromethene and phosphorus-azadipyrromethene dye: PODIPY/aza-PODIPY.
PODIPY and aza-PODIPY have been successfully prepared by the treatment of dipyrromethene and azadipyrromethene with POCl3 in the presence of Et3 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.
College of Applied Chemistry, Shenyang University of chemical Technology, Shenyang, 110142 (P.R. China). xdjiang@syuct.edu.cn.
Xin-Dong
XD
Jiang
Jiuli
J
Zhao
Dongmei
D
Xi
Haifeng
H
Yu
Jian
J
Guan
Shuang
S
Li
Chang-Liang
CL
Sun
Lin-Jiu
LJ
Xiao
D001372:Aza Compounds / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D008958:Models, Molecular; D061848:Optical Imaging; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry
D001372:Aza Compounds; D005456:Fluorescent Dyes; D009943:Organophosphorus Compounds; C507544:dipyrromethene; D014867:Water; D011162:Porphobilinogen
PODIPY; fluorescent probes; phosphorus; photophysical properties; water soluble