Pyrrolylmethylene Appended Corrorin: Peripheral Coordination and Transformation to Pyridyl Incorporated Hemiporphycene AnalogueShow others and affiliations
2023 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 25, no 10, p. 1793-1798Article in journal (Refereed) Published
Abstract [en]
A pyrrolylmethylene appended corrorin 1 was synthesized and coordinated with [Rh(CO)2Cl]2 to afford 1-Rh with unique RhI-eta 2-CC bonding in addition to the coordination of the dipyrrin-like unit and a carbonyl ligand. Further oxidation of 1 afforded 2, exhibiting a hydrocorrorinone core, and it can be further transformed into pyrrolo[3,2c]pyridine incorporated hemiporphycene analogue 3 upon treatment with HOAc. The side chain modifies the reactivity of corrorin and effectively tunes the NIR absorption of the resulting porphyrinoids.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2023. Vol. 25, no 10, p. 1793-1798
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-499933DOI: 10.1021/acs.orglett.3c00595ISI: 000946486100001PubMedID: 36881833OAI: oai:DiVA.org:uu-499933DiVA, id: diva2:1749300
Funder
Swedish National Infrastructure for Computing (SNIC)Swedish Research Council, 2018-05973Swedish Research Council, 2020-046002023-04-062023-04-062023-04-06Bibliographically approved