Synthesis and properties of hybrid porphyrin tapes

Takayuki Tanaka, Byung Sun Lee, Naoki Aratani, Min Chul Yoon, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Hybrid porphyrin tapes 3 and 4, consisting of a mixture of 3,5-di-tert-butylphenyl-substituted donor-type Zn II-porphyrins and pentafluorophenyl-substituted acceptor-type Zn II-porphyrins, were prepared by a synthetic route involving cross-condensation reaction of a Ni II-porphyrinyldipyrromethane and pentafluorophenyldipyrromethane with pentafluorobenzaldehyde followed by appropriate demetalation, remetalation, and oxidative ring-closure reaction. The Ni II-substituted porphyrin tapes 5 (Ni-Zn-Ni) and 6 (Ni-H 2-Ni) were also prepared through similar routes. The hybrid porphyrin tapes 3 and 4 are more soluble and more stable than normal porphyrin tapes 1 and 2 consisting of only donor-type Zn II-porphyrins. The solid-state and crystal packing structures of 3, 4, and 5 were elucidated by single-crystal X-ray diffraction analysis. Singly meso-meso-linked hybrid porphyrin arrays 12 and 14 exhibit redox potentials that roughly correspond to each constituent porphyrin segments, while the redox potentials of the hybrid porphyrin tapes 3 and 4 are positively shifted as a whole. The two-photon absorption (TPA) values of 1-6 were measured by using a wavelength-scanning open aperture Z-scan method and found to be 1900, 21 000, 2200, 27 000, 24 000, and 26 000 GM, respectively. These results illustrate an important effect of elongation of π-electron conjugation for the enhancement of TPA values. The hybrid porphyrin tapes show slightly larger TPA values than the parent ones.

Original languageEnglish
Pages (from-to)14400-14412
Number of pages13
JournalChemistry - A European Journal
Volume17
Issue number51
DOIs
Publication statusPublished - 2011 Dec 16

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Porphyrins
Tapes
Photons
Condensation reactions
X ray diffraction analysis
Elongation
Single crystals
Scanning
Wavelength
Crystals

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Tanaka, T., Lee, B. S., Aratani, N., Yoon, M. C., Kim, D., & Osuka, A. (2011). Synthesis and properties of hybrid porphyrin tapes. Chemistry - A European Journal, 17(51), 14400-14412. https://doi.org/10.1002/chem.201102889
Tanaka, Takayuki ; Lee, Byung Sun ; Aratani, Naoki ; Yoon, Min Chul ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis and properties of hybrid porphyrin tapes. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 51. pp. 14400-14412.
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Tanaka, T, Lee, BS, Aratani, N, Yoon, MC, Kim, D & Osuka, A 2011, 'Synthesis and properties of hybrid porphyrin tapes', Chemistry - A European Journal, vol. 17, no. 51, pp. 14400-14412. https://doi.org/10.1002/chem.201102889

Synthesis and properties of hybrid porphyrin tapes. / Tanaka, Takayuki; Lee, Byung Sun; Aratani, Naoki; Yoon, Min Chul; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 17, No. 51, 16.12.2011, p. 14400-14412.

Research output: Contribution to journalArticle

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T1 - Synthesis and properties of hybrid porphyrin tapes

AU - Tanaka, Takayuki

AU - Lee, Byung Sun

AU - Aratani, Naoki

AU - Yoon, Min Chul

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2011/12/16

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AB - Hybrid porphyrin tapes 3 and 4, consisting of a mixture of 3,5-di-tert-butylphenyl-substituted donor-type Zn II-porphyrins and pentafluorophenyl-substituted acceptor-type Zn II-porphyrins, were prepared by a synthetic route involving cross-condensation reaction of a Ni II-porphyrinyldipyrromethane and pentafluorophenyldipyrromethane with pentafluorobenzaldehyde followed by appropriate demetalation, remetalation, and oxidative ring-closure reaction. The Ni II-substituted porphyrin tapes 5 (Ni-Zn-Ni) and 6 (Ni-H 2-Ni) were also prepared through similar routes. The hybrid porphyrin tapes 3 and 4 are more soluble and more stable than normal porphyrin tapes 1 and 2 consisting of only donor-type Zn II-porphyrins. The solid-state and crystal packing structures of 3, 4, and 5 were elucidated by single-crystal X-ray diffraction analysis. Singly meso-meso-linked hybrid porphyrin arrays 12 and 14 exhibit redox potentials that roughly correspond to each constituent porphyrin segments, while the redox potentials of the hybrid porphyrin tapes 3 and 4 are positively shifted as a whole. The two-photon absorption (TPA) values of 1-6 were measured by using a wavelength-scanning open aperture Z-scan method and found to be 1900, 21 000, 2200, 27 000, 24 000, and 26 000 GM, respectively. These results illustrate an important effect of elongation of π-electron conjugation for the enhancement of TPA values. The hybrid porphyrin tapes show slightly larger TPA values than the parent ones.

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