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Issue 3, 2013
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2,3,17,18-Tetraethylsulfanyl [30]hexaphyrin(1.1.1.1.1.1) as the first aromatic isophlorin-type free-base

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Abstract

β-Tetraethylsulfanyl-substituted [28]hexaphyrin 5 was prepared and converted to the corresponding β-tetraethylsulfonyl [28]hexaphyrin 6 and tetraethylsulfanyl [26]hexaphyrin 7. Both 5 and 6 are antiaromatic molecules with figure-of-eight structures while the major conformer of 7 is an aromatic species with a rectangular shape. Thorough reduction of 5 with NaBH4 produced tetraethylsulfanyl [30]hexaphyrin 8 as the first example of expanded isophlorin free-base with distinct 30π aromaticity.

Graphical abstract: 2,3,17,18-Tetraethylsulfanyl [30]hexaphyrin(1.1.1.1.1.1) as the first aromatic isophlorin-type free-base

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Publication details

The article was received on 20 Oct 2012, accepted on 03 Dec 2012 and first published on 06 Dec 2012


Article type: Edge Article
DOI: 10.1039/C2SC21791K
Citation: Chem. Sci., 2013,4, 1087-1091

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    2,3,17,18-Tetraethylsulfanyl [30]hexaphyrin(1.1.1.1.1.1) as the first aromatic isophlorin-type free-base

    T. Higashino and A. Osuka, Chem. Sci., 2013, 4, 1087
    DOI: 10.1039/C2SC21791K

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