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New Near‐Infrared‐Fluorescent Aza‐BODIPY Dyes with 1‐Methyl‐1 H ‐Pyrrolyl Substituents at the 3,5‐Positions
Author(s) -
Jiang XinDong,
Guan Jian,
Li Qian,
Sun Changliang
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600201
Subject(s) - bodipy , chemistry , fluorescence , photochemistry , infrared , absorption (acoustics) , materials science , physics , quantum mechanics , optics , composite material
New near‐infrared‐fluorescent aza‐BODIPY dyes with 1‐methyl‐1 H ‐pyrrolyl substituents at the 3,5‐positions were successfully prepared and the 1‐methyl‐1 H ‐pyrrolyl groups had a noticeable effect on their photophysical properties. The absorption and emission maxima of aza‐BODIPY dye 4 ( λ abs =754 nm, λ em =803 nm) that contained 1‐methyl‐1 H ‐pyrrolyl groups were bathochromically shifted compared to those of typical aza‐BODIPY dye 1 ( λ abs =649 nm, λ em =673 nm), which contained phenyl groups. The photophysical data were well‐supported and explained by MO calculations. Aza‐BODIPY dye 3 was stable and suited for labeling living cells for imaging assays in the near‐infrared region.