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Molecules. 2017 Jun 15;22(6). pii: E994. doi: 10.3390/molecules22060994.

Coumarin-Tetrapyrrolic Macrocycle Conjugates: Synthesis and Applications.

Author information

1
Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal. anacerqueira@ua.pt.
2
Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal. v.almodovar@ua.pt.
3
Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal. gneves@ua.pt.
4
Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal. actome@ua.pt.

Abstract

This review covers the synthesis of coumarin-porphyrin, coumarin-phthalocyanine and coumarin-corrole conjugates and their potential applications. While coumarin-phthalocyanine conjugates were obtained almost exclusively by tetramerization of coumarin-functionalized phthalonitriles, coumarin-porphyrin and coumarin-corrole conjugates were prepared by complementary approaches: (a) direct synthesis of the tetrapyrrolic macrocycle using formylcoumarins and pyrrole or (b) by functionalization of the tetrapyrrolic macrocycle. In the last approach a range of reaction types were used, namely 1,3-dipolar cycloadditions, hetero-Diels-Alder, Sonogashira, alkylation or acylation reactions. This is clearly a more versatile approach, leading to a larger diversity of conjugates and allowing the access to conjugates bearing one to up to 16 coumarin units.

KEYWORDS:

corroles; coumarins; phthalocyanines; porphyrins

PMID:
28617340
PMCID:
PMC6152750
DOI:
10.3390/molecules22060994
[Indexed for MEDLINE]
Free PMC Article

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