Boron-dipyrromethene (BODIPY) is a class of fluorescent dyes with a variety of uses including medical imaging, diagnostics, and photodynamic therapy. Due to the instability of the compound in the body, it is desirable to substitute the two fluorine atoms using methanol to make the compound safer and more stable in vivo.In the following study, we examined the nucleophilic substitution mechanism of the reaction of BODIPY to create the dimethoxy-substituted BODIPY by calculating the potential energy surface including intermediates and transition states involved. We compared possible SN1 and SN2 reaction pathways for the formation of dimethoxy-substituted BODIPY to determine which of the proposed mechanisms was more probable. All calculations were done using Density Functional Theory to locate potential energy stationary points for each mechanism, taking into account the effect of the solvent. Charges for each of the atoms involved were calculated using Natural Population Analysis to help better explain the differences between the two reaction pathways. 

Computational insights into the reaction mechanism of the synthesis of dimethoxy-substituted BODIPY

247th National Meeting (2014)

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