Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza-s-indacene dyes: Synthesis and spectroscopic evaluation.
A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon lambda max approximately 80,000 M(-1) cm(-1)), and for most of them high fluorescence quantum yields (Phi exp from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2 h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.
Tahtaoui
Chouaib
C
Département de Pharmacochimie de la Communication Cellulaire, Institut Gilbert Laustriat, UMR 7175-LC1 ULP/CNRS, Faculté de Pharmacie de Strasbourg, 74 Route du Rhin, 67401 Illkirch, France.
Thomas
Cécile
C
Rohmer
François
F
Klotz
Philippe
P
Duportail
Guy
G
Mély
Yves
Y
Bonnet
Dominique
D
Hibert
Marcel
M
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*
D001372:Aza Compounds; D005456:Fluorescent Dyes; D010100:Oxygen