Synthesis and properties of hybrid porphyrin tapes

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

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61 Citations (Scopus)


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
Issue number51
Publication statusPublished - 2011 Dec 16

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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