Triphyrin(2.1.1) with Tunable Skeletons and Properties Based on the Confusion Approach

Gaojie Zhu; Feng Sha; Bin Zhu; Mingbo Zhou; Hailong Wang; Glib Baryshnikov; Chengjie Li; Hans Ågren; Jianxin Song; Jianzhuang Jiang; Qizhao Li; Yongshu Xie

doi:10.1021/acs.orglett.4c03395

Triphyrin(2.1.1) with Tunable Skeletons and Properties Based on the Confusion Approach

Org Lett. 2024 Nov 15;26(45):9671-9675. doi: 10.1021/acs.orglett.4c03395. Epub 2024 Nov 1.

Authors

Gaojie Zhu¹, Feng Sha¹, Bin Zhu¹, Mingbo Zhou², Hailong Wang³, Glib Baryshnikov⁴, Chengjie Li¹, Hans Ågren⁵, Jianxin Song², Jianzhuang Jiang³, Qizhao Li^{1

2}, 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 Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Ministry of Educational of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
³ Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry and Chemical Engineering, School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, China.
⁴ Department of Science and Technology, Laboratory of Organic Electronics, Linköping University, Norrköping SE-60174, Sweden.
⁵ Department of Physics and Astronomy Uppsala University Box 516, Uppsala SE-75120, Sweden.

PMID: 39486048
DOI: 10.1021/acs.orglett.4c03395

Abstract

The N-confused [14]triphyrin(2.1.1) 1 was facilely synthesized and readily converted into N-confused triphyrinone(2.1.1) 2 and α-methoxy-substituted 1-OMe. Subsequent acid-promoted ring-opening of 1-OMe afforded vacatatriphyrin(2.1.1) 3. Further treatment of 3 with CuCl₂·2H₂O resulted in ring-closure and tetrachlorination to furnish 2H-triphyrin(2.1.0) 4. As a result of the diverse structures achieved through the confusion approach, the aromaticity, absorption, and electrochemical properties could be effectively tuned.