Pyrrolylmethylene Appended Corrorin: Peripheral Coordination and Transformation to Pyridyl Incorporated Hemiporphycene Analogue

Yue Xu; Bin Zhu; Qizhao Li; Feng Sha; Glib Baryshnikov; Lanka He; Yifan Feng; Jingxuan Tang; Yuan Wei; Chengjie Li; Xinyan Wu; Hans Ågren; Yongshu Xie

doi:10.1021/acs.orglett.3c00595

Pyrrolylmethylene Appended Corrorin: Peripheral Coordination and Transformation to Pyridyl Incorporated Hemiporphycene Analogue

Org Lett. 2023 Mar 17;25(10):1793-1798. doi: 10.1021/acs.orglett.3c00595. Epub 2023 Mar 7.

Authors

Yue Xu¹, Bin Zhu¹, Qizhao Li¹, Feng Sha¹, Glib Baryshnikov², Lanka He¹, Yifan Feng¹, Jingxuan Tang¹, Yuan Wei¹, Chengjie Li¹, Xinyan Wu¹, Hans Ågren³, Yongshu Xie¹

Affiliations

¹ Key Laboratory for Advanced Materials, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.
² Department of Science and Technology, Laboratory of Organic Electronics, Linköping University, SE-601 74 Norrköping, Sweden.
³ Department of Physics and Astronomy, Uppsala University, SE-751 20 Uppsala, Sweden.

PMID: 36881833
DOI: 10.1021/acs.orglett.3c00595

Abstract

A pyrrolylmethylene appended corrorin 1 was synthesized and coordinated with [Rh(CO)₂Cl]₂ to afford 1-Rh with unique Rh^I-η²-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[3,2-c]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.