Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes

Yang Liu; Ling Xu; Yutao Rao; Jinseok Kim; Bangshao Yin; Mingbo Zhou; Juwon Oh; Dongho Kim; Jianxin Song; Atsuhiro Osuka

doi:10.1021/acs.orglett.3c03231

Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes

Yang Liu, Ling Xu, Yutao Rao, Jinseok Kim, Bangshao Yin, Mingbo Zhou, Juwon Oh, Dongho Kim, Jianxin Song, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

5,10,23-Trimesityl-substituted [24]hexaphyrin(1.1.0.0.1.0) was synthesized as a stable antiaromatic molecule by base-catalyzed twofold S_NAr reaction and was reduced to the corresponding [26]hexaphyrin, which was an unstable aromatic molecule because it easily oxidized to the [24]hexaphyrin. The [24]hexaphyrin served as a ligand to give the bis-Pd^II complex and tris-Rh^I complex with unique structures. The former complex has two square-planar-coordinated Pd^II ions bridged by an acetate anion and shows a strong paratropic ring current, while the latter complex has three Rh^I ions coordinated with two pyrrolic nitrogen atoms and two carbonyl groups, but one carbonyl group is shared with two Rh^I ions in a unique manner.

Original language	English
Pages (from-to)	8121-8126
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	45
DOIs	https://doi.org/10.1021/acs.orglett.3c03231
State	Published - 17 Nov 2023

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title = "Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes",

abstract = "5,10,23-Trimesityl-substituted [24]hexaphyrin(1.1.0.0.1.0) was synthesized as a stable antiaromatic molecule by base-catalyzed twofold SNAr reaction and was reduced to the corresponding [26]hexaphyrin, which was an unstable aromatic molecule because it easily oxidized to the [24]hexaphyrin. The [24]hexaphyrin served as a ligand to give the bis-PdII complex and tris-RhI complex with unique structures. The former complex has two square-planar-coordinated PdII ions bridged by an acetate anion and shows a strong paratropic ring current, while the latter complex has three RhI ions coordinated with two pyrrolic nitrogen atoms and two carbonyl groups, but one carbonyl group is shared with two RhI ions in a unique manner.",

author = "Yang Liu and Ling Xu and Yutao Rao and Jinseok Kim and Bangshao Yin and Mingbo Zhou and Juwon Oh and Dongho Kim and Jianxin Song and Atsuhiro Osuka",

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doi = "10.1021/acs.orglett.3c03231",

language = "English",

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T1 - Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes

AU - Liu, Yang

AU - Xu, Ling

AU - Rao, Yutao

AU - Kim, Jinseok

AU - Yin, Bangshao

AU - Zhou, Mingbo

AU - Oh, Juwon

AU - Kim, Dongho

AU - Song, Jianxin

AU - Osuka, Atsuhiro

PY - 2023/11/17

Y1 - 2023/11/17

N2 - 5,10,23-Trimesityl-substituted [24]hexaphyrin(1.1.0.0.1.0) was synthesized as a stable antiaromatic molecule by base-catalyzed twofold SNAr reaction and was reduced to the corresponding [26]hexaphyrin, which was an unstable aromatic molecule because it easily oxidized to the [24]hexaphyrin. The [24]hexaphyrin served as a ligand to give the bis-PdII complex and tris-RhI complex with unique structures. The former complex has two square-planar-coordinated PdII ions bridged by an acetate anion and shows a strong paratropic ring current, while the latter complex has three RhI ions coordinated with two pyrrolic nitrogen atoms and two carbonyl groups, but one carbonyl group is shared with two RhI ions in a unique manner.

AB - 5,10,23-Trimesityl-substituted [24]hexaphyrin(1.1.0.0.1.0) was synthesized as a stable antiaromatic molecule by base-catalyzed twofold SNAr reaction and was reduced to the corresponding [26]hexaphyrin, which was an unstable aromatic molecule because it easily oxidized to the [24]hexaphyrin. The [24]hexaphyrin served as a ligand to give the bis-PdII complex and tris-RhI complex with unique structures. The former complex has two square-planar-coordinated PdII ions bridged by an acetate anion and shows a strong paratropic ring current, while the latter complex has three RhI ions coordinated with two pyrrolic nitrogen atoms and two carbonyl groups, but one carbonyl group is shared with two RhI ions in a unique manner.

UR - http://www.scopus.com/inward/record.url?scp=85177103765&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c03231

DO - 10.1021/acs.orglett.3c03231

M3 - Article

C2 - 37930089

AN - SCOPUS:85177103765

SN - 1523-7060

VL - 25

SP - 8121

EP - 8126

JO - Organic Letters

JF - Organic Letters

IS - 45

ER -

Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes

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