21‐Carba‐23‐selenaporphyrinoid Dyads—An Azepine Unit as a Merging Motif

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Abstract

The oxidation of 10,15‐diaryl‐21‐carba‐23‐selenaporphyrinoids resulted in the creation of dyads. The dimerization process follows a [5+2] cycloaddition path with the formation of an azepine unit. The arrays display two direct bonds between the peripheral carbocyclic carbon atoms of one carbaselenaporphyrinic subunit and the central carbon and nitrogen atoms of the second subunit. This results in a unique canted arrangement of two carbaporphyrinoid planes resembling an open seashell‐like motif.

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Photoinduced electron transfer in supramolecular systems for artificial photosynthesis

Michael Wasielewski (1992)

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Fully conjugated porphyrin tapes with electronic absorption bands that reach into infrared.

A Tsuda, A Osuka (2001)

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 approximately 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.