| Autor: |
Diaz-Rodriguez RM; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada. alison.thompson@dal.ca., Burke L, Robertson KN, Thompson A |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2020 Mar 18; Vol. 18 (11), pp. 2139-2147. |
| DOI: |
10.1039/d0ob00272k |
| Abstrakt: |
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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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