Metal-Assisted Oxidative Cyclization of Vinylene-Bridged Hexapyrrane
Oxidative cyclization of vinylene-bridged hexapyrrane P6 afforded nonconjugated meso-hydroxy derivative of vinylene-bridged hexaphyrin (1). Whereas, Cu(II)-mediated oxidation afforded novel homoporphyrin-dipyrrin hybrid 2-Cu and cage-like homoporphyrin-calixphyrin chimera 3-Cu. By contrast, employment of Zn(II) only afforded 3-Zn. Due to the presence of chiral centers in 1 and 2-Cu, they can be separated into enantiomers with near-infrared chiroptical properties. This work reveals the potential of metal-mediated oxidation in synthesizing porphyrinoids with diverse structures.
Authors
- Qizhao Li (ORCID: https://orcid.org/0000-0002-2046-7041)
- Su-Hong Peng
- Hans Ågren (ORCID: https://orcid.org/0000-0002-1763-9383)
- Yongshu Xie (ORCID: https://orcid.org/0000-0001-8230-7599)
- Glib Baryshnikov (ORCID: https://orcid.org/0000-0002-0716-3385)
- Guangyun Wu
- Zimei Ma
- Gaojie Zhu
Institutions
- Linköping University (SE)
- Uppsala University (SE)
- East China University of Science and Technology (CN)
- Yichun University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-11-06
- DOI
- https://doi.org/10.1021/acs.orglett.6c04508
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Science and Technology Commission of Shanghai Municipality
- Vetenskapsrådet
- Science and Technology Program of Hunan Province
- European Research Council
- Key Science and Technology Research Project in Jiangxi Province Department of Education