meso-Tetrahexyl-7,8-dihydroxychlorin and Its Conversion to ß-Modified Derivatives
Daniel Aicher, Dinusha Damunupola, Christian B. W. Stark, Arno Wiehe, Christian Brückner
TL;DR
This paper describes the synthesis and functionalization of a new type of chlorin compound with potential for various chemical modifications.
Contribution
The study introduces a new class of versatile chlorins based on meso-tetrahexyl-7,8-dihydroxychlorin and their functionalization capabilities.
Findings
The diol chlorin can be oxidized to form a chlorin dione and porpholactone.
The diol chlorin undergoes dehydration to form a porphyrin enol in equilibrium with its keto-chlorin form.
The meso-hexylchlorin dione can be reduced and methylated using various reagents.
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…
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Taxonomy
TopicsPorphyrin and Phthalocyanine Chemistry · Photodynamic Therapy Research Studies · Heme Oxygenase-1 and Carbon Monoxide