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Boron–Phenylpyrrin Dyes: Facile Synthesis, Structure, and pH‐Sensitive Properties
Author(s) -
Chen Yuting,
Qi Dongdong,
Zhao Luyang,
Cao Wei,
Huang Chunhua,
Jiang Jianzhuang
Publication year - 2013
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.201203345
Subject(s) - boron , protonation , chemistry , stokes shift , salicylaldehyde , fluorescence , photochemistry , red shift , bodipy , absorption spectroscopy , absorption (acoustics) , ring (chemistry) , inorganic chemistry , polymer chemistry , organic chemistry , materials science , ion , physics , schiff base , quantum mechanics , galaxy , composite material
Boron–phenylpyrrin dyes : In the presence of BF 3 ⋅OEt 2 , 4‐(diethylamino)salicylaldehyde reacts with substituted pyrroles to give boron–phenylpyrrin dyes, which contain a central boron‐containing seven‐membered ring. Upon protonation in acidic solution, the complexes, with a large Stokes shift, exhibit a color change and a unique red shift in both the electronic absorption and fluorescence emission spectra (see picture), thus rendering them new analogues of boron–dipyrrin dyes that can be used as pH sensors.