Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 40, Pages 12854-12863Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201399
Keywords
ab initio calculations; cations; conjugation; electronic structure; porphyrinoids
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Funding
- MEXT [21108517]
- JSPS [20550047]
- Grants-in-Aid for Scientific Research [23550018, 20550047, 23350020, 21108517, 24655018] Funding Source: KAKEN
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Bicyclo[2.2.2]octadiene (BCOD) fused azuliporphyrins were synthesized by 3+1 porphyrin synthesis of azulitripyrranes with diformylpyrroles. Subsequent retro-Diels-Alder reaction of the BCOD-fused azuliporphyrins afforded azulibenzo, azulidibenzo-, and azulitribenzoporphyrins 1-5. NMR and UV/Vis spectra, as well as nucleus-independent chemical shift (NICS) calculations revealed that 1-5 and their diprotonated dications exhibit relatively low porphyrinoid aromaticity, which was dependent on the position and number of fused benzene rings present.
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