1,7-Disubstituted Boron Dipyrromethene (BODIPY) Dyes: Synthesis and Spectroscopic Properties

Abstract

1,7-Dihalogenated boron dipyrromethene dyes were successfully synthesized and substituted, thus providing an entry to the final, elusive reactivity pattern. The spectroscopic properties of 1,7-disubstituted BODIPY dyes were studied and are discussed as a function of their structure.

Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY

“…18 This material exhibits a bathochromic shift of ~30 nm compared to the unsubstituted BODIPY dye, 19 with absorption and emission maxima ranging from 550 nm to 570 nm, with emission quantum yields ranging from 0.30 in non-polar environments to 0.07 in polar media. Figure 2.…”

Synthesis and regioselective functionalization of perhalogenated BODIPYs

“…10 Such halogenated derivatives can be the precursors of a wide range of functionalized BODIPY dyes for various applications, via Pd(0) catalyzed cross-coupling reactions (e.g., the Suzuki, Stille, Heck or Sonogashira reactions) and/or substitution reactions with C-, N-, O-, or S-nucleophiles. 11 On the other hand, halogen groups can be selectively introduced into the 3,5-positions, 10a the 2,6-, 7,12 1,7-, 13 and 8-position 14 , allowing the subsequent introduction of various functional groups to specific positions by subsequent Pd(0) cross-coupling reactions or/and substitution reactions. The platforms with 3,5-halogens 10a or/and 8-halogens 14 have attracted considerable interest due to the large distribution of the HOMO and LUMO at the 3,5-positions and 8-position, respectively.…”

New Trends in Near-Infrared Fluorophores for Bioimaging

“…The degree of the bathochromic shift depends on the introduction positions: a modification at the 3-/5-position has a more drastic effect than at the 1-/7-or 2-/6-position. 40,45,49 Some of the 3-/5-substituted BODIPYs are commercially available. 21 These aryl moieties can be easily introduced via palladium-catalyzed coupling reactions (for all) 46 or Knoevenagel condensation (for vinylaryl BODIPY), 42,44 allowing easy tuning of the fluorescence wavelength.…”