1. meso -Tetrahexyl-7,8-dihydroxychlorin and Its Conversion to ß-Modified Derivatives.
- Author
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Aicher, Daniel, Damunupola, Dinusha, Stark, Christian B. W., Wiehe, Arno, and Brückner, Christian
- Subjects
GLYCOLS ,CHLORINS ,OXIDATION states ,PORPHYRINS ,OPTICAL properties ,MOIETIES (Chemistry) - Abstract
meso-Tetrahexylporphyrin was converted to its corresponding 7,8-dihydroxychlorin using an osmium tetroxide-mediated dihydroxylation strategy. Its diol moiety was shown to be able to undergo a number of subsequent oxidation reactions to form a chlorin dione and porpholactone, the first meso-alkylporphyrin-based porphyrinoid containing a non-pyrrolic building block. Further, the diol chlorin was shown to be susceptible to dehydration, forming the porphyrin enol that is in equilibrium with its keto-chlorin form. The meso-hexylchlorin dione could be reduced and it underwent mono- and bis-methylation reactions using methyl-Grignard reagents, and trifluoromethylation using the Ruppert-Prakash reagent. The optical and spectroscopic properties of the products are discussed and contrasted to their corresponding meso-aryl derivatives (where known). This contribution establishes meso-tetrahexyl-7,8-dihydroxychlorins as a new and versatile class of chlorins that is susceptible to a broad range of conversions to generate functionalized chlorins and a pyrrole-modified chlorin analogue. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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