Synthesis of SF5-Substituted Tetrapyrroles, Metalloporphyrins, BODIPYs, and Their Dipyrrane Precursors
| Autor: | Hans-Ulrich Reissig, Hartwig R. A. Golf, Arno Wiehe |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Boron Compounds
Cycloaddition Reaction Molecular Structure Sulfur Compounds Metalloporphyrins Aryl Organic Chemistry Stereoisomerism Combinatorial chemistry Cycloaddition chemistry.chemical_compound chemistry Tetrapyrroles Nucleophilic aromatic substitution Coordination Complexes Moiety Sodium azide Organic chemistry Surface modification Corrole BODIPY Palladium Pyrans |
| Zdroj: | The Journal of organic chemistry. 80(10) |
| ISSN: | 1520-6904 |
| Popis: | The synthesis of novel pentafluorosulfanyl (SF5)-substituted A4-type porphyrins, their corresponding Zn(II)- and Pd(II)-metal complexes, A3-, A2B- and AB2-type corroles, BODIPYs, and their dipyrrane precursors was studied utilizing commercially available SF5-substituted aryl aldehydes. In addition, the functionalization of SF5-substituted tetrapyrroles was investigated by applying the concept of the nucleophilic aromatic substitution (S(N)Ar) with alcohols and sodium azide onto the pentafluorophenyl moiety of a trans-A2B2-porphyrin and two corrole derivatives with a mixed substitution pattern involving the SF5 group. This allows a fine-tuning of the properties of these macrocycles through a selective and mild introduction of functional groups, giving access to multifunctionalized SF5-substituted porphyrinoids. As an example, one functionalized corrole was further reacted with an azido-substituted BODIPY via the copper(I)-catalyzed 1,3-dipolar cycloaddition yielding the first corrole-BODIPY heterodimer involving the pentafluorosulfanyl group. |
| Databáze: | OpenAIRE |
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