Porphyriynes: 18-π-Conjugated Macrocycles Incorporating a Triple Bond

Fei Hao; Tian Zhang; Donghai Yu; Xiaodeng Yang; Hua-Wei Jiang; Ji-Chang Xiao; Qing-Yun Chen

doi:10.1021/acs.orglett.2c00356

Porphyriynes: 18-π-Conjugated Macrocycles Incorporating a Triple Bond

Org Lett. 2022 Mar 4;24(8):1716-1721. doi: 10.1021/acs.orglett.2c00356. Epub 2022 Feb 24.

Authors

Fei Hao^{1

2}, Tian Zhang¹, Donghai Yu², Xiaodeng Yang¹, Hua-Wei Jiang³, Ji-Chang Xiao², Qing-Yun Chen²

Affiliations

¹ Shandong Provincial Key Laboratory of Molecular Engineering, Qilu University of Technology-Shandong Academy of Science, Ji'nan 250353, China.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
³ School of Chemistry, South China Normal University, Guangzhou 510006, China.

PMID: 35199515
DOI: 10.1021/acs.orglett.2c00356

Abstract

Tetraphenylporphyriyne (Pyne1), a novel porphyrin analogue with a C≡C bond incorporated into an 18-π-conjugated system, has been created via cleavage of the N-confused pyrrolic ring in Ag(III) N-confused tetraphenylporphyrin. The structure of Pyne1 was confirmed by X-ray crystallography and ¹H NMR, IR, and UV-vis spectroscopy. The mechanism of cleavage of the N-confused pyrrolic ring was investigated by theoretical calculations. The successful synthesis of other Pynes indicated the generality of this protocol.