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Synthesis of zinc 20-substituted bacteriochlorophyll-danalogs and their self-aggregation

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Volume
55
Issue
22
Identifiers
DOI: 10.1016/j.tetlet.2014.04.057
Keywords
  • Chlorosome
  • Cross-Coupling
  • Pyropheophorbide
  • Substitution Effect

Abstract

Abstract Zinc complexes of methyl 31-demethyl-bacteriopheophorbides-d possessing a 2-(un)substituted ethynyl or ethenyl group at the 20-position were prepared through palladium-catalyzed cross-coupling of their 20-bromide with the corresponding alkyne or alkene. The synthetic zinc 20-substituted 3-hydroxymethyl-131-oxo-chlorins self-aggregated in an aqueous micellar solution to give similar large oligomers as self-aggregates of bacteriochlorophylls in the core part of the main light-harvesting antenna of photosynthetic green bacteria. The zinc 20-ethynyl-chlorin fully gave the self-aggregates, but its 202-substitution disturbed the self-aggregation. The 20-(2-phenyl)ethenyl moieties induced the formation of relatively smaller oligomers as well as residual monomers due to their steric bulkiness.

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