BODIPYDIPYrromethene BOron Difluoride
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We applied iridium-catalyzed direct borylation to BODIPY dye 48 and dipyrromethane 51 (Scheme 23).
beta]-Borylated BODIPY 50 was also prepared through palladium-catalyzed borylation of bromo BODIPY 56, which was obtained by regioselective bromination of BODIPY 48 with N-bromosuccinimide (Scheme 25).
These aromatic molecules absorb photons at a shorter wavelength than F-BODIPY and transfer their energy to the BODIPY core, which can then release the energy through fluorescent decay (Ulrich et al.
1] because substituted chromophores are not in conjugation with the BODIPY core (Goze et al.
Herein, we report the synthesis of substituted BODIPY compounds under mild reaction conditions in reasonable yield.
In addition, Brominated BODIPY could be the valuable precursor for functionalisation of the BODIPY core by coupling reactions.
5 shows the observed fluorescence emission when an ethanol solution of green BODIPY [R] dye was placed in a fluorimeter and excited with 555 nm light.
The dipyrromethane is aromatized (chloranil or DDQ are commonly used) resulting in a dipyrromethene (or dipyrrin) that is ultimately converted to the BODIPY by complexation with a difluoroboryl unit in a base-catalyzed reaction with trifluoroboryl etherate (B[F.
BODIPY compounds have superior photochemical and photophysical characteristics such as high chemical and photostability, high absorption coefficients, high fluorescence quantum yields, and narrow absorption and emission bands (Loudet & Burgess 2007; Ulrich et al.
5] Nonstandard abbreviations: MSP, methylation-specific PCR; MS-FLAG, methylation-specific fluorescent amplicon generation; LAMP, loop-mediated isothermal amplification; dNTP, deoxynucleoside triphosphate; MS-LAMP, methylation-specific LAMP; BODIPY, dipyrromethene boron difluoride; TAMRA, 6-carboxytetramethylrhodamine.
15 mmol/L BODIPY FL phallacidin (Molecular Probes) in PBS containing 10 g/L bovine serum albumin (BSA) for 20 min at room temperature, washed 3 times with PBS, and mounted in SlowFade (Molecular Probes).