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Issue 46, 2016
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Remarkable acceleration of template-directed photodimerisation of 9-phenylethynylanthracene derivatives assisted by complementary salt bridge formation

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Abstract

The photoirradiation of 9-phenylethynylanthracene in degassed chloroform and benzene afforded not only a [4 + 2]-anti Diels–Alder addition dimer, but also a [4 + 4]-anti-dimer as a minor product for the first time as revealed by single-crystal X-ray analysis, while the anthracene residue was quantitatively oxidised in undegassed dilute chloroform, giving the corresponding endoperoxides. The photochemical reactions of carboxylic acid monomers bearing a 9-phenylethynylanthracene unit at one and both ends were further investigated in the presence and absence of the complementary amidine dimer as the template. It was found that a similar photooxidation reaction of the monomers was significantly suppressed in the presence of the template even in undegassed chloroform. In addition, the template-directed photodimerisation of the mono- and di-9-phenylethynylanthracene-bound monomers was remarkably accelerated 30- or 61-fold in the degassed chloroform, giving the [4 + 2]-anti- and [4 + 4]-anti-dimers as major and minor products, respectively, whereas the di-9-phenylethynylanthracene-bound monomer was preferentially photo-polymerised in the absence of the template.

Graphical abstract: Remarkable acceleration of template-directed photodimerisation of 9-phenylethynylanthracene derivatives assisted by complementary salt bridge formation

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Publication details

The article was received on 23 Sep 2016, accepted on 12 Oct 2016 and first published on 12 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB02087A
Citation: Org. Biomol. Chem., 2016,14, 10822-10832
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    Remarkable acceleration of template-directed photodimerisation of 9-phenylethynylanthracene derivatives assisted by complementary salt bridge formation

    J. Tanabe, D. Taura, N. Ousaka and E. Yashima, Org. Biomol. Chem., 2016, 14, 10822
    DOI: 10.1039/C6OB02087A

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