Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 36, Pages 10639-10642Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505124
Keywords
aromaticity; circulenes; cyclooctatetraene; fused-ring systems; pyrroles
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Funding
- JSPS KAKENHI [25220802, 25620031, 20705446]
- Global Research Laboratory (GRL) Program - Ministry of Science, ICT and Future, Korea [2013K1A1A2A02050183]
- Grants-in-Aid for Scientific Research [26810021, 15H01001, 15H00756, 26708003] Funding Source: KAKEN
- National Research Foundation of Korea [2013K1A1A2A02050183, 21A20131312351, 2005-0093839] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Tetrabenzotetraaza[8]circulene (1) has been synthesized in good yield by a fold-in oxidative fusion reaction of a 1,2-phenylene-bridged cyclic tetrapyrrole. X-ray diffraction analysis of 1 has revealed a planar square structure with a central cyclooctatetraene (COT) core that shows little alternation of the bond lengths. Despite these structural features, 1 shows aromatic-like character, such as sharp absorption bands, high fluorescence quantum yields (phi(F)=0.55 in THF), and a single exponential fluorescence decay with (F)=3.8ns. These observations indicate a dominant contribution of an [8]radialene-like conjugation and hence aromatic character of the local aromatic segments in 1.
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