High Stokes Shift Anilido‐Pyridine Boron Difluoride Dyes

Abstract

Neue Farben: Über drei verwandte Fluoreszenzfarbstoffklassen, die durch eine Bordifluorid‐Gruppe starr sind und aus zweizähnigen Anilidopyridylliganden bestehen (siehe Bild), wird berichtet. Die Farbstoffe zeigen Quantenausbeuten bis 0.75 und eine mehr als 100 nm stärkere Stokes‐Verschiebung als die BODIPY‐Farbstoffe. Zudem sind sie außergewöhnlich photostabil und membranspezifisch.

Asymmetric anthracene-fused BODIPY dye with large Stokes shift: Synthesis, photophysical properties and bioimaging

“…Compared with that of BODIPY 1, the emission spectrum of BODIPY 2 exhibits a notable red shift (more than 110 nm) with l em,max more than 637 nm, indicating that BODIPY 2 may be a good candidate for saturated-red fluorescent bioimaging. Moreover, it is notable that the Stokes shift has increased from 294 cm À1 (8 nm) for BODIPY 1 to 1425 cm À1 (53 nm) for BODIPY 2, perhaps due to the formation of dimer [10c] and the desymmetrization of BODIPY 2 [18]. The fluorescence quantum yield (40% in chloroform) of BODIPY 2 is much higher than that (0.4% in chloroform) of BODIPY 1 and also higher than that of other "zig-zag" ring fused BODIPY [14].…”

Naphthalene-fused BODIPY with large Stokes shift as saturated-red fluorescent dye for living cell imaging

“…Moreover, it is notable that the Stokes shift has increased from 8 nm for 1 to 56 nm for 2, perhaps due to the formation of dimer [21] and the desymmetrization of the molecule 2. [22] The fluorescence quantum yield (44 % in chloroform) of 2 is a little higher than that (39 % in chloroform) of 1 and much higher than that of other zig-ag ring fused BODIPY.…”

Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes

“…Intermediate (1) was synthesized as previously reported [40]. The monobromo intermediate (4) was prepared by first bromination of (1) with NBS to get (2) [41] followed by N-alkylation with bromoethane in the presence of NaOH in acetone [42]. It is important to mention here that this pathway for the preparation of (4) was found to be much easier as compared to the previously reported method [31] of doing Nalkylation first and then bromination which resulted into the formation of both mono-and dibromocarbazoles, (4) and (5) respectively, which were not easily separable by column chromatography (due to very close R f values) or by recrystallization (due to quite similar solubilities).…”