A mono-meso-free N-confused hexaphyrin with tunable NIR absorption: synthesis, coordination, and oxidative dimerization

Lingfang Zhang; Zhengpeng Huang; Qizhao Li; Glib Baryshnikov; Bin Zhu; Mingbo Zhou; Chengjie Li; Hans Ågren; Shijun Li; Jianxin Song; Yongshu Xie

doi:10.1039/D6QO00221H

A mono-meso-free N-confused hexaphyrin with tunable NIR absorption: synthesis, coordination, and oxidative dimerization

Lingfang Zhang,^a Zhengpeng Huang,^a Qizhao Li,

^a Glib Baryshnikov,

^b Bin Zhu,^a Mingbo Zhou,^c Chengjie Li,

^a Hans Ågren,^de Shijun Li,

^f Jianxin Song

^c and Yongshu Xie

*^a

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, 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, China

^b Department of Science and Technology, Laboratory of Organic Electronics, Linköping University, SE-60174 Norrköping, Sweden

^c 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

^d Department of Physics and Astronomy, Uppsala University, Box 516, SE-75120 Uppsala, Sweden

^e Faculty of Chemistry, Wroclaw University of Science and Technology, Wyb. Wyspianskiego 27, PL-50370 Wroclaw, Poland

^f College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, China

Abstract

A weakly Möbius aromatic mono-meso-free N-confused hexaphyrin 1 was synthesized and oxidized into a C_meso–C_meso linked dimer (1)₂. Interestingly, metallation of 1 with Cu(II) in MeCN/MeOH afforded not only 1-Cu but also three complexes of ligands generated in situ by oxygenation and methoxylation of 1 at the meso- and α-positions.

Organic Chemistry Frontiers

A mono-meso-free N-confused hexaphyrin with tunable NIR absorption: synthesis, coordination, and oxidative dimerization

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A mono-meso-free N-confused hexaphyrin with tunable NIR absorption: synthesis, coordination, and oxidative dimerization

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