Synthesis of direct β-to-β linked porphyrin arrays with large electronic interactions: Branched and cyclic oligomers

Hao Cai; Keisuke Fujimoto; Jong Min Lim; Chaojie Wang; Weiming Huang; Yutao Rao; Senmiao Zhang; Hui Shi; Bangshao Yin; Bo Chen; Ming Ma; Jianxin Song; Dongho Kim; Atsuhiro Osuka

doi:10.1002/anie.201407032

Synthesis of direct β-to-β linked porphyrin arrays with large electronic interactions: Branched and cyclic oligomers

Hao Cai, Keisuke Fujimoto, Jong Min Lim, Chaojie Wang, Weiming Huang, Yutao Rao, Senmiao Zhang, Hui Shi, Bangshao Yin, Bo Chen, Ming Ma, Jianxin Song, Dongho Kim, Atsuhiro Osuka

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35 Scopus citations

Abstract

Direct β-to-β linked branched and cyclic porphyrin trimers and pentamers have been synthesized by the Suzuki-Miyaura coupling of β-borylporphyrins and β-bromoporphyrins. The cyclic porphyrin trimer, the smallest directly linked cyclic porphyrin wheel to date, and its twined pentamer, exhibit small electrochemical HOMO-LUMO gaps, broad nonsplit Soret bands, and red-shifted Q-bands, thus indicating large electronic interactions between the constituent porphyrin units.

Original language	English
Pages (from-to)	11088-11091
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	41
DOIs	https://doi.org/10.1002/anie.201407032
State	Published - 6 Oct 2014

Keywords

cross-coupling
cyclization
energy transfer
porphyrinoids
structure elucidation

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Cai, H., Fujimoto, K., Lim, J. M., Wang, C., Huang, W., Rao, Y., Zhang, S., Shi, H., Yin, B., Chen, B., Ma, M., Song, J., Kim, D., & Osuka, A. (2014). Synthesis of direct β-to-β linked porphyrin arrays with large electronic interactions: Branched and cyclic oligomers. Angewandte Chemie - International Edition, 53(41), 11088-11091. https://doi.org/10.1002/anie.201407032

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abstract = "Direct β-to-β linked branched and cyclic porphyrin trimers and pentamers have been synthesized by the Suzuki-Miyaura coupling of β-borylporphyrins and β-bromoporphyrins. The cyclic porphyrin trimer, the smallest directly linked cyclic porphyrin wheel to date, and its twined pentamer, exhibit small electrochemical HOMO-LUMO gaps, broad nonsplit Soret bands, and red-shifted Q-bands, thus indicating large electronic interactions between the constituent porphyrin units.",

keywords = "cross-coupling, cyclization, energy transfer, porphyrinoids, structure elucidation",

author = "Hao Cai and Keisuke Fujimoto and Lim, {Jong Min} and Chaojie Wang and Weiming Huang and Yutao Rao and Senmiao Zhang and Hui Shi and Bangshao Yin and Bo Chen and Ming Ma and Jianxin Song and Dongho Kim and Atsuhiro Osuka",

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T1 - Synthesis of direct β-to-β linked porphyrin arrays with large electronic interactions

T2 - Branched and cyclic oligomers

AU - Cai, Hao

AU - Fujimoto, Keisuke

AU - Lim, Jong Min

AU - Wang, Chaojie

AU - Huang, Weiming

AU - Rao, Yutao

AU - Zhang, Senmiao

AU - Shi, Hui

AU - Yin, Bangshao

AU - Chen, Bo

AU - Ma, Ming

AU - Song, Jianxin

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2014/10/6

Y1 - 2014/10/6

N2 - Direct β-to-β linked branched and cyclic porphyrin trimers and pentamers have been synthesized by the Suzuki-Miyaura coupling of β-borylporphyrins and β-bromoporphyrins. The cyclic porphyrin trimer, the smallest directly linked cyclic porphyrin wheel to date, and its twined pentamer, exhibit small electrochemical HOMO-LUMO gaps, broad nonsplit Soret bands, and red-shifted Q-bands, thus indicating large electronic interactions between the constituent porphyrin units.

AB - Direct β-to-β linked branched and cyclic porphyrin trimers and pentamers have been synthesized by the Suzuki-Miyaura coupling of β-borylporphyrins and β-bromoporphyrins. The cyclic porphyrin trimer, the smallest directly linked cyclic porphyrin wheel to date, and its twined pentamer, exhibit small electrochemical HOMO-LUMO gaps, broad nonsplit Soret bands, and red-shifted Q-bands, thus indicating large electronic interactions between the constituent porphyrin units.

KW - cross-coupling

KW - cyclization

KW - energy transfer

KW - porphyrinoids

KW - structure elucidation

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 41

ER -

Synthesis of direct β-to-β linked porphyrin arrays with large electronic interactions: Branched and cyclic oligomers

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Keywords

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