π-extended "earring" porphyrins with multiple cavities and near-infrared absorption

Yutao Rao; Taeyeon Kim; Kyu Hyung Park; Fulei Peng; Lei Liu; Yunmei Liu; Bin Wen; Shubin Liu; Steven Robert Kirk; Licheng Wu; Bo Chen; Ming Ma; Mingbo Zhou; Bangshao Yin; Yuexing Zhang; Dongho Kim; Jianxin Song

doi:10.1002/anie.201600955

π-extended "earring" porphyrins with multiple cavities and near-infrared absorption

Yutao Rao, Taeyeon Kim, Kyu Hyung Park, Fulei Peng, Lei Liu, Yunmei Liu, Bin Wen, Shubin Liu, Steven Robert Kirk, Licheng Wu, Bo Chen, Ming Ma, Mingbo Zhou, Bangshao Yin, Yuexing Zhang, Dongho Kim, Jianxin Song

Department of Chemistry

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

18 Citations (Scopus)

Abstract

β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties. Porphyrins with ears: β,β-Tripyrrin-bridged "earring" porphyrins were synthesized by Suzuki-Miyaura cross coupling reactions. These compounds have multiple cavities that can complex up to three metal ions. The porphyrin structures feature curved π planes, and their electronic spectra show near-infrared (NIR) absorptions. Metal insertion leads to red-shifted and intensified near-infrared absorption features.

Original language	English
Pages (from-to)	6438-6442
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	22
DOIs	https://doi.org/10.1002/anie.201600955
Publication status	Published - 2016 May 23

Bibliographical note

Funding Information:
We thank Dr. Zier Yan (Rigaku Beijing Corporation, China) for help in crystallographic analysis. The work at Hunan Normal University was supported by the National Natural Science Foundation of China. (Grant No. 21272065), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, and Scientific Research Fund of Hunan Provincial Education Department (Grant No.13k027). The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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Rao, Yutao ; Kim, Taeyeon ; Park, Kyu Hyung ; Peng, Fulei ; Liu, Lei ; Liu, Yunmei ; Wen, Bin ; Liu, Shubin ; Kirk, Steven Robert ; Wu, Licheng ; Chen, Bo ; Ma, Ming ; Zhou, Mingbo ; Yin, Bangshao ; Zhang, Yuexing ; Kim, Dongho ; Song, Jianxin. / π-extended "earring" porphyrins with multiple cavities and near-infrared absorption. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 22. pp. 6438-6442.

@article{269d6604c9dd462a94012f38b2b0b000,

title = "π-extended {"}earring{"} porphyrins with multiple cavities and near-infrared absorption",

abstract = "β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties. Porphyrins with ears: β,β-Tripyrrin-bridged {"}earring{"} porphyrins were synthesized by Suzuki-Miyaura cross coupling reactions. These compounds have multiple cavities that can complex up to three metal ions. The porphyrin structures feature curved π planes, and their electronic spectra show near-infrared (NIR) absorptions. Metal insertion leads to red-shifted and intensified near-infrared absorption features.",

author = "Yutao Rao and Taeyeon Kim and Park, {Kyu Hyung} and Fulei Peng and Lei Liu and Yunmei Liu and Bin Wen and Shubin Liu and Kirk, {Steven Robert} and Licheng Wu and Bo Chen and Ming Ma and Mingbo Zhou and Bangshao Yin and Yuexing Zhang and Dongho Kim and Jianxin Song",

note = "Funding Information: We thank Dr. Zier Yan (Rigaku Beijing Corporation, China) for help in crystallographic analysis. The work at Hunan Normal University was supported by the National Natural Science Foundation of China. (Grant No. 21272065), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, and Scientific Research Fund of Hunan Provincial Education Department (Grant No.13k027). The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = may,

day = "23",

doi = "10.1002/anie.201600955",

language = "English",

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pages = "6438--6442",

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π-extended "earring" porphyrins with multiple cavities and near-infrared absorption. / Rao, Yutao; Kim, Taeyeon; Park, Kyu Hyung; Peng, Fulei; Liu, Lei; Liu, Yunmei; Wen, Bin; Liu, Shubin; Kirk, Steven Robert; Wu, Licheng; Chen, Bo; Ma, Ming; Zhou, Mingbo; Yin, Bangshao; Zhang, Yuexing; Kim, Dongho; Song, Jianxin.

In: Angewandte Chemie - International Edition, Vol. 55, No. 22, 23.05.2016, p. 6438-6442.

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

TY - JOUR

T1 - π-extended "earring" porphyrins with multiple cavities and near-infrared absorption

AU - Rao, Yutao

AU - Kim, Taeyeon

AU - Park, Kyu Hyung

AU - Peng, Fulei

AU - Liu, Lei

AU - Liu, Yunmei

AU - Wen, Bin

AU - Liu, Shubin

AU - Kirk, Steven Robert

AU - Wu, Licheng

AU - Chen, Bo

AU - Ma, Ming

AU - Zhou, Mingbo

AU - Yin, Bangshao

AU - Zhang, Yuexing

AU - Kim, Dongho

AU - Song, Jianxin

N1 - Funding Information: We thank Dr. Zier Yan (Rigaku Beijing Corporation, China) for help in crystallographic analysis. The work at Hunan Normal University was supported by the National Natural Science Foundation of China. (Grant No. 21272065), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, and Scientific Research Fund of Hunan Provincial Education Department (Grant No.13k027). The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2016/5/23

Y1 - 2016/5/23

N2 - β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties. Porphyrins with ears: β,β-Tripyrrin-bridged "earring" porphyrins were synthesized by Suzuki-Miyaura cross coupling reactions. These compounds have multiple cavities that can complex up to three metal ions. The porphyrin structures feature curved π planes, and their electronic spectra show near-infrared (NIR) absorptions. Metal insertion leads to red-shifted and intensified near-infrared absorption features.

AB - β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties. Porphyrins with ears: β,β-Tripyrrin-bridged "earring" porphyrins were synthesized by Suzuki-Miyaura cross coupling reactions. These compounds have multiple cavities that can complex up to three metal ions. The porphyrin structures feature curved π planes, and their electronic spectra show near-infrared (NIR) absorptions. Metal insertion leads to red-shifted and intensified near-infrared absorption features.

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M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 22

ER -

π-extended "earring" porphyrins with multiple cavities and near-infrared absorption

Abstract

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