Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 46, Pages 10822-10832Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02087a
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Funding
- JSPS KAKENHI [25220804, 26810048]
- JSPS [8886]
- Grants-in-Aid for Scientific Research [14J08886, 26810048, 16H01016, 16K17892] Funding Source: KAKEN
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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.
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