BODIPY Dye, the Most Versatile Fluorophore Ever?

Abstract

BODIPY laser dyes constitute a fascinating topic of research in modern photochemistry due to the large variety of options its chromophore offers, which is ready available for a multitude of synthetic routes. Indeed, in the literature one can find a huge battery of compounds based on the indacene core. The possibility of modulating the spectroscopic properties or inducing new photophysical processes by the substitution pattern of the BODIPY dyes has boosted the number of scientific and technological applications for these fluorophores. Along the following lines, I will overview the main results achieved in our laboratory with BODIPYs oriented to optoelectronic as well to biophotonic applications, stressing the more relevant photophysical issues to be considered in the design of a tailor-made BODIPY for a certain application and pointing out some of the remaining challenges.

N‐BODIPYs Come into Play: Smart Dyes for Photonic Materials

“…BODIPYs (boron dipyrromethenes; 4‐bora‐3a,4a‐diaza‐ s ‐indacenes) constitute one of the most valuable families of technological dyes . Nowadays, there is a plethora of available synthetic procedures for their direct functionalization, focused on appropriate modulation of key physical (mainly photophysical) properties .…”

Self-Assembly of Bodipy-Derived Extended π-Systems

“…Although Bodipy resembles the mono-methine dyes, a closer inspection reveals that the chromophore consists of 12 π-electrons distributed over 11 atoms, making it isoelectronic with heptamethine cyanines. 30,31,37 The name boradiazaindacene is analogous to that of the all-carbon tricyclic ring and the 8-position of the tricyclic ring is referred as 'meso' similar to that of the porphyrinic systems. Condensation reaction between highly electrophilic carbonyl compounds such as acyl chloride, acid anhydride and aldehyde with two pyrrole units in presence of a base is the general way for the preparation of Bodipy dyes.…”

Photoactive Nanomaterials Inspired by Nature: LTL Zeolite Doped with Laser Dyes as Artificial Light Harvesting Systems

“…The label is an organosilane moiety linked to the above head through a spacer bearing a long enough polymethylene chain at the para position of a sterically-hindered phenyl grafted at the chromophoric meso position (Figure 6). Such a constrained structure around the key meso position is essential to avoid any non-radiative pathway associated with the conformational freedom of the aryl and to keep the excellent fluorescence response of BODIPYs [42]. The triethoxysilane label penetrates into the channels and reacts with the zeolitic silanols after hydrolysis and polycondensation reactions, plugging the channel entrances.…”