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Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold

Date

2020-02-25

Authors

Diaz-Rodriguez, Roberto M.
Burke, Luke
Robertson, Katherine N.
Thompson, Alison

Journal Title

Journal ISSN

Volume Title

Publisher

Royal Society of Chemistry

Abstract

The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub- types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl–B–F intermediate, is implicated in the conversion of F-aza-BODIPYs to Cl-aza-BODIPYs upon treatment with BCl3. The utility of the Cl-aza-BODIPY scaffold to facilitate substitutions at boron is demonstrated under mild conditions through treatment with aryl Grignard reagents. Additionally, the lability of the B–Cl bond enables facile removal of the BCl2 group, i.e. deprotection of F-aza-BODIPYs, under aqueous conditions. Three aza- dipyrrin HX salts were also synthesised and characterised. The pKa of the protonated aza-dipyrrin was determined to be 4, thereby providing insight regarding the storage and stability of such species.

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Citation

Diaz-Rodriguez, R. M., Burke, L., Robertson, K. N., & Thompson, A. (2020). Synthesis, properties and reactivity of BCl 2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold. Organic & Biomolecular Chemistry, 18(11), 2139-2147.

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