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Science 6 July 2001:
Vol. 293. no. 5527, pp. 79 - 82
DOI: 10.1126/science.1059552
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Reports

Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared

Akihiko Tsuda, Atsuhiro Osuka*

Scandium(III)-catalyzed oxidation of meso-meso-linked zinc(II)-porphyrin arrays (up to dodecamers) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) led to efficient formation of triply meso-meso-, beta -beta -, and beta -beta -linked zinc(II)-oligoiporphyrins with 62 to 91% yields. These fused tape-shaped porphyrin arrays display extremely red-shifted absorption bands that reflect extensively pi -conjugated electronic systems and a low excitation gap. The lowest electronic absorption bands become increasingly intensified and red-shifted upon the increase in the number of porphyrins and eventually reach a peak electronic excitation for the dodecamer at ~3500 wavenumber. The one-electron oxidation potentials also decreased progressively upon the increase in the number of porphyrins. These properties in long and rigid molecular shapes suggest their potential use as molecular wires.

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
*   To whom correspondence should be addressed.

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THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Molecular Recognition and Self-Assembly Special Feature: Supramolecular polymer formed by reversible self-assembly of tetrakisporphyrin.
T. Haino, T. Fujii, A. Watanabe, and U. Takayanagi (2009)
PNAS 106, 10477-10481
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