Synthesis and properties of chiral fluorescent helicene-BODIPY conjugates

A series of chiral fluorescent helicene-BODIPY conjugates was prepared by the regioselective formylation of aza[4]helicene precursors and then an efficient one-pot two-step BODIPY synthesis (13 examples, 28-82%). Fused conjugates exhibit absorption and fluorescence properties (ΦF30-45%) in the red visible domain, and a CPL signature could be measured at 605 nm (glum±5 × 10−4). Photophysical and electronic properties were investigated and rationalized through first principles

Functionalized cationic [4]helicenes with unique tuning of absorption, fluorescence and chiroptical properties up to the far-red range

Unprecedented regioselective post-functionalization of racemic and enantiopure cationic diaza [4]helicenes is afforded. The peripheral auxochrome substituents allow a general tuning of the electrochemical, photophysical and chiroptical properties of the helical dyes (26 examples). For instance, electronic absorption and circular dichroism are modulated from the orange to near-infrared spectral range (575–750 nm), fluorescence quantum efficiency is enhanced up to 0.55 (631 nm) and circularly polarized luminescence is recorded in the red (|glum| ∼ 10−3)