Solid-Emissive BODIPY Derivatives: Design, Synthesis and Applications

Structural modification strategies for the rational design of red/NIR region BODIPYs

“…Over the past decade there has been considerable interest in the synthesis of organic chromophores with strong absorption and fluorescence bands in the near-IR (NIR) region primarily because of advances in optical techniques for imaging, in microarrays, and in electrophoresis, and the need for 5 rapidly. 34,[37][38][39][40][41] This has been related to, (i) their facile synthesis and structural versatility, (ii) their excellent spectroscopic properties (narrow Gaussian-shaped absorption and emission bands, high molar extinction coefficients (usually ε > 80 000 M −1 .cm −1 ) and Φ F values (commonly Φ > 0.50), moderate redox potentials, negligible triplet-state formation and negligible sensitivity to solvent polarity, excellent photostability, and high solubility in commonly used organic solvents of differing polarities), and (iii) their wide range of potential applications in numerous research fields. 32,33,[37][38][39][40] A major drawback, however, is that the spectral properties of the classic BODIPY chromophore are typically limited to the 470 -530 nm region.…”

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

“…Up to now, there have been a few techniques to construct solid-emissive boron-diuoride complexes, such as introducing bulky groups around the BF 2 chelate to alleviate the intermolecular p-p stacking by steric effect and designing intermolecular noncovalent bonding to promote non-parallel packing. 5 During the recent years, we have adopted the second technique to develop a series of boron-diuoride dyes based on the ligand of 2-(2 0 -pyridyl) imidazole derivatives, and found that these boron-diuoride dyes (BOPIM) exhibit quite large stokes shi (over 100 nm) and high uorescence intensity in the solid state. [6][7][8][9][10][11] It seems that low-symmetrization of the structures is quite effective to cause more energetically distinguished ground and excited states to enlarge the Stokes shi.…”

Radical CH Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids

“…Fluorescence of boron dipyrrins in diluted solution is a well‐known phenomenon. Solid‐state emissive BODIPYs, on the other hand, are far less commonly reported 25. Nevertheless, such solid‐state emissive dyes are interesting compounds with several applications in the field of optoelectronics, including organic light‐emitting diodes26 and organic photovoltaic devices 5.…”

“…The above results clearly highlight the utility of the described radical alkylation method, as it readily gives access to solid‐state emissive dyes by introducing multiple bulky alkyl substituents onto the BODIPY core in one reaction step. In contrast, preparation of the few solid‐state emissive boron dipyrrins currently described in literature require a longer synthetic route 25…”