Synthesis of nanometer-scale porphyrin wheels of variable size

Takaaki Hori, Xiaobin Peng, Naoki Aratani, Akihiko Takagi, Takuya Matsumoto, Tomoji Kawai, Zin Seok Yoon, Min Chul Yoon, Jaesung Yang, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Starting from 1.3-phenylene linked diporphyrin zinc(II) complex 2ZA. repeated stepwise Ag1-promoted coupling reactions provided linear oligomers from 2nZA up to 128ZA. Of these zigzag shaped porphyrin arrays. the Ag'-promoted intramolecular cyclization reaction of 2nZA (n = 5. 6. 8. 9, 12, and 16) under dilute conditions gave the corresponding cyclic porphyrin wheels C2wZA (n=5, 6. 8. 9, 12, and 16), whereas large arrays 2nZA (n = 24, 32. and 48) did not providecyclic porphyrin products. These large discrete porphyrin arrays and wheels were fully characterized by means of 1HNMR spectroscopy, MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, GPC-HPLC analysis, and the scanning tunneling microscopy (STM) technique. The STM images of C12ZA and C18ZA reveal their large circular structures. In the cyclic structures of C2nZA in solution, however, the gradual decrease in fluorescence quantum yields and fluorescence lifetimes are observed, reflecting some conformational heterogeneities. Collectively, the present work provides an important contribution to the construction of fully covalently linked large cyclic arranged porphyrin arrays with ample electronic interactions as a model of light-harvesting antenna.

Original languageEnglish
Pages (from-to)582-595
Number of pages14
JournalChemistry - A European Journal
Volume14
Issue number2
DOIs
Publication statusPublished - 2008 Jan 22

Fingerprint

Porphyrins
Wheels
Scanning tunneling microscopy
Fluorescence
Cyclization
Quantum yield
Ultraviolet spectroscopy
Absorption spectroscopy
Oligomers
Mass spectrometry
Zinc
Spectroscopy
Antennas

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Hori, T., Peng, X., Aratani, N., Takagi, A., Matsumoto, T., Kawai, T., ... Osuka, A. (2008). Synthesis of nanometer-scale porphyrin wheels of variable size. Chemistry - A European Journal, 14(2), 582-595. https://doi.org/10.1002/chem.200701271
Hori, Takaaki ; Peng, Xiaobin ; Aratani, Naoki ; Takagi, Akihiko ; Matsumoto, Takuya ; Kawai, Tomoji ; Yoon, Zin Seok ; Yoon, Min Chul ; Yang, Jaesung ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis of nanometer-scale porphyrin wheels of variable size. In: Chemistry - A European Journal. 2008 ; Vol. 14, No. 2. pp. 582-595.
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Hori, T, Peng, X, Aratani, N, Takagi, A, Matsumoto, T, Kawai, T, Yoon, ZS, Yoon, MC, Yang, J, Kim, D & Osuka, A 2008, 'Synthesis of nanometer-scale porphyrin wheels of variable size', Chemistry - A European Journal, vol. 14, no. 2, pp. 582-595. https://doi.org/10.1002/chem.200701271

Synthesis of nanometer-scale porphyrin wheels of variable size. / Hori, Takaaki; Peng, Xiaobin; Aratani, Naoki; Takagi, Akihiko; Matsumoto, Takuya; Kawai, Tomoji; Yoon, Zin Seok; Yoon, Min Chul; Yang, Jaesung; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 14, No. 2, 22.01.2008, p. 582-595.

Research output: Contribution to journalArticle

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T1 - Synthesis of nanometer-scale porphyrin wheels of variable size

AU - Hori, Takaaki

AU - Peng, Xiaobin

AU - Aratani, Naoki

AU - Takagi, Akihiko

AU - Matsumoto, Takuya

AU - Kawai, Tomoji

AU - Yoon, Zin Seok

AU - Yoon, Min Chul

AU - Yang, Jaesung

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2008/1/22

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AB - Starting from 1.3-phenylene linked diporphyrin zinc(II) complex 2ZA. repeated stepwise Ag1-promoted coupling reactions provided linear oligomers from 2nZA up to 128ZA. Of these zigzag shaped porphyrin arrays. the Ag'-promoted intramolecular cyclization reaction of 2nZA (n = 5. 6. 8. 9, 12, and 16) under dilute conditions gave the corresponding cyclic porphyrin wheels C2wZA (n=5, 6. 8. 9, 12, and 16), whereas large arrays 2nZA (n = 24, 32. and 48) did not providecyclic porphyrin products. These large discrete porphyrin arrays and wheels were fully characterized by means of 1HNMR spectroscopy, MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, GPC-HPLC analysis, and the scanning tunneling microscopy (STM) technique. The STM images of C12ZA and C18ZA reveal their large circular structures. In the cyclic structures of C2nZA in solution, however, the gradual decrease in fluorescence quantum yields and fluorescence lifetimes are observed, reflecting some conformational heterogeneities. Collectively, the present work provides an important contribution to the construction of fully covalently linked large cyclic arranged porphyrin arrays with ample electronic interactions as a model of light-harvesting antenna.

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Hori T, Peng X, Aratani N, Takagi A, Matsumoto T, Kawai T et al. Synthesis of nanometer-scale porphyrin wheels of variable size. Chemistry - A European Journal. 2008 Jan 22;14(2):582-595. https://doi.org/10.1002/chem.200701271