Boron dipyrromethanes

Daub, Grimme, and coworkers have reported chiroptical switches based on binaphthyl boron dipyrromethane (BDP) conjugates. It is known that BDP dyes with appropriate functionalization can be reversibly oxidized and reduced.58 The CD-spectroelectrochemical studies of R-56 show a decrease in the intensity of the Cotton effect at 501 nm by applying a reduction potential to the solution. The initial CD spectrum is restored completely after reoxidation thus, the CD signal intensity at 501 nm for R-56 can be switched on and off electrochemically.59... 

Membrane-bound probes, which are incorporated directly during vesicle preparation, are commonly fluorescently labeled phospholipids. These probes are mainly used to address more complex changes in membrane structure, thereby providing insights into the structure and mechanism of the transporters. Depending on the specific desired application, various fluorescently labeled phospholipids are available. Popular examples include boron dipyrromethane (BODIPY) probes as FRET acceptors, DOXYL probes as quenchers for parallax analysis, 7-nitro-benzofurazan (NBD) probes such as NBD-POPE for flip-flop assay, and so on (Figure 8). 

Figure 6.6 Hexa-pen-hexabenzocoronene (HBC) 22, corannulene 23, tetrathiaftjivalene (TTF) 24, tetracyanoquinodimethane (TCNQ) 25, porphyrin 26 and boron dipyrromethanes (BOD-IPYs) 27.

The reaction comprises the following steps reduction of 2-trifluoroacetylpyrroles, condensation of the alcohols formed with pyrroles to dipyrromethanes (Scheme 2.187, Table 2.18), their oxidation to dipyrromethenes, and complex formation of the latter with boron trifluoride. The last two stages proceed in a one-pot manner. 

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