Strategic Construction of Directly Linked Porphyrin–BODIPY Hybrids

Lei Xu; Bin Wen; Gakhyun Kim; Taeyeon Kim; Fei Cheng; Mingbo Zhou; Ling Xu; Takayuki Tanaka; Bangshao Yin; Atsuhiro Osuka; Dongho Kim; Jianxin Song

doi:10.1002/anie.201707237

Strategic Construction of Directly Linked Porphyrin–BODIPY Hybrids

Lei Xu, Bin Wen, Gakhyun Kim, Taeyeon Kim, Fei Cheng, Mingbo Zhou, Ling Xu, Takayuki Tanaka, Bangshao Yin, Atsuhiro Osuka, Dongho Kim, Jianxin Song

Department of Chemistry

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

20 Citations (Scopus)

Abstract

A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl Ni^II-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF₃⋅Et₂O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some Ni^II porphyrins were effectively converted to the corresponding Zn^II porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.

Original language	English
Pages (from-to)	12322-12326
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	40
DOIs	https://doi.org/10.1002/anie.201707237
Publication status	Published - 2017 Sept 25

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© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.201707237

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title = "Strategic Construction of Directly Linked Porphyrin–BODIPY Hybrids",

abstract = "A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl NiII-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF3⋅Et2O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some NiII porphyrins were effectively converted to the corresponding ZnII porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.",

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AU - Xu, Lei

AU - Wen, Bin

AU - Kim, Gakhyun

AU - Kim, Taeyeon

AU - Cheng, Fei

AU - Zhou, Mingbo

AU - Xu, Ling

AU - Tanaka, Takayuki

AU - Yin, Bangshao

AU - Osuka, Atsuhiro

AU - Kim, Dongho

AU - Song, Jianxin

PY - 2017/9/25

Y1 - 2017/9/25

N2 - A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl NiII-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF3⋅Et2O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some NiII porphyrins were effectively converted to the corresponding ZnII porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.

AB - A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl NiII-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF3⋅Et2O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some NiII porphyrins were effectively converted to the corresponding ZnII porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.

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Strategic Construction of Directly Linked Porphyrin–BODIPY Hybrids

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