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Start Over Author "Xie, Yongshu" Journal angewandte chemie
15 results on '"Xie, Yongshu"'

2. Antiaromatic Sapphyrin Isomer: Transformation into Contracted Porphyrinoids with Variable Aromaticity.

Author

Li, Qizhao, Ishida, Masatoshi, Wang, Yunyun, Li, Chengjie, Baryshnikov, Glib, Zhu, Bin, Sha, Feng, Wu, Xinyan, Ågren, Hans, Furuta, Hiroyuki, and Xie, Yongshu

Subjects
ISOMERS, AROMATICITY, RING formation (Chemistry), ANTIAROMATICITY, ELECTRONIC structure, PYRROLES, PORPHYRINS, ERGOT alkaloids
Abstract

Sapphyrin is a pentapyrrolic expanded porphyrin with a 22π aromatic character. Herein, we report the synthesis of a 20π antiaromatic sapphyrin isomer 1 by oxidative cyclization of a pentapyrrane precursor P5 with a terminal β‐linked pyrrole. The resulting isomer 1, containing a mis‐linked bipyrrole unit in the skeleton, exhibits a reactivity for further oxidation due to the distinct antiaromatic electronic structure, affording a fused macrocycle 2, possessing a spiro‐carbon‐containing [5.6.5.6]‐tetracyclic structure. Subsequent treatment with an acid afforded a weakly aromatic pyrrolone‐appended N‐confused corrole 3, and thermal fusion gave a [5.6.5.7]‐tetracyclic‐ring‐embedded 14π aromatic triphyrin(2.1.1) analog 4. The cyclization at the mis‐linked pyrrole moiety of P5 played a crucial role in synthesizing the antiaromatic porphyrinoid susceptible to facile transformation to novel porphyrinoids with variable aromaticity. [ABSTRACT FROM AUTHOR]

Published
2023
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5. N‐Confused Phlorin‐Prodigiosin Chimera: meso‐Aryl Oxidation and π‐Extension Triggered by Peripheral Coordination.

Author

Su, Guangxian, Li, Qizhao, Ishida, Masatoshi, Li, Chengjie, Sha, Feng, Wu, Xin‐Yan, Wang, Lu, Baryshnikov, Glib, Li, Dawei, Ågren, Hans, Furuta, Hiroyuki, and Xie, Yongshu

Subjects
PHENOXY groups, OXIDATION, ISOMERS
Abstract

An N‐confused phlorin isomer bearing a dipyrrin moiety at the α‐position of the confused pyrrole ring (1) was synthesized. PdII and BIII coordination at the peripheral prodigiosin‐like moiety of 1 afforded the corresponding complexes 2 and 3. Reflux of 2 in triethylamine (TEA) converted the meso‐phenyl into the PdII‐coordinating phenoxy group to afford 4. Under the same reaction conditions, TEA was linked to the α‐position of the dipyrrin unit in 3 as an N,N‐diethylaminovinyl group to afford 5. Furthermore, peripheral coordination of BIII in 3 and 5 improved the planarity of the phlorin macrocycle and thus facilitated the coordination of AgIII at the inner cavity to afford 3‐Ag and 5‐Ag, respectively. These results provide an effective approach for developing unique porphyrinoids through peripheral coordination. [ABSTRACT FROM AUTHOR]

Published
2020
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