One-Pot Synthesis of Four Chlorin Derivatives by a Divergent Ylide.

ABSTRACT: Chlorins have unique photophysical properties that are exploited in diverse biological and materials applications. De novo chlorin synthesis with specific exocyclic motifs can be challenging and many are not stable to photobleaching and/or oxidation. A facile approach to a stable synthetic chlorin with a fused N-methyl pyrrolidine uses cyclo addition of a sarcosine-based azomethine ylide on 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)-porphyrin (TPPF₂₀) is reported, but this approach has limitations. We report the synthesis of stable chlorin scaffolds starting with TPPF₂₀ using a new glycine-based N-(hydroxymethyl)- N-methelenemethanideaminium ylide. Careful control of the 1,3-dipolar cycloaddition reaction allows a divergent use of the glycine derived ylide to yi

SUBMITTER: Gonzales J 

PROVIDER: S-EPMC6175582 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature