NDLI: Synthesis and Properties of Hybrid Porphyrin Tapes

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Synthesis and Properties of Hybrid Porphyrin Tapes

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Synthesis and Properties of Hybrid Porphyrin Tapes

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Aratani, Naoki Kim, Dongho Yoon, Min-chul Osuka, Atsuhiro Tanaka, Takayuki Lee, Byung Sun
Description	Author Affiliation: Tanaka T ( Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.)
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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	51
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-12-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Porphyrins Chemical Synthesis Crystallography, X-Ray Molecular Structure Nickel Chemistry Organometallic Compounds X-Ray Diffraction Zinc Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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