Synthesis of 8-(3,5-dimethoxyphenyl) bodipy and its formylation reaction

BODIPY,4,,4a-diaza-s-indacene, is a highly versatile dye family.Its unique features include stability against light and chemicals, high absorption and emission intensities, adjustable fluorescence quantum yield by functional group modifications, and a large molar absorption coefficient.As a result of these impressive properties of BODIPY dyes, the dyes have been studied and utilized in various areas such as chemistry, biology, and materials science, for example, photodynamic therapy reagents, photosensitizers in solar cells, chemosensors, fluorescent tags in biomolecule labelling and cell imaging, laser dyes, and molecular logic gate.Smart synthetic strategies can be utilized to obtain BODIPY dyes, such as halogen insertion, formylation, introduction of heteroatom, fusion of aromatic, heteroaromatic, and non-aromatic rings, and connecting other fluorescent dyes and modification by organometallic crosscoupling reactions, Knoevenagel condensation.By these synthetic methods, the photophysical parameters of BODIPY dyes can be tailored to meet application requirements.The compounds with aldehyde functional groups are very versatile tools to attain a wide variety of compounds.In this study, the BODIPY dye was synthesized by condensation with pyrrole and 3,5dimethoxybenzaldehyde by using trifluoroacetic acid followed by oxidation by DDQ and complexation with boron difluoride (BF 3 .OEt 2 ).Finally, the dye was formylated by Vilsmeier Haack reaction using POCl 3 -DMF.Both of the compounds were identified by 1 H, 13 C, and 19 F NMR spectra.The structure of formylated BODIPY was confirmed by the peaks that appeared at 9.86 and 185.07 ppm at 1 H and 13 C NMR spectra, respectively