Nonplanar aromatic compounds. 9. Synthesis, structure, and aromaticity of 1:2,13:14-dibenzo[2]paracyclo[2](2,7)- pyrenophane-1,13-diene |
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Authors: | Zhang Baozhong Manning Gregory P Dobrowolski Michał A Cyrański Michał K Bodwell Graham J |
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Affiliation: | Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7. |
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Abstract: | Pyrenophane (6) and an octaphenyl derivative (16) were synthesized using two different routes. Both cyclophanes contain a severely bent pyrene unit (6: theta = 93.6 degrees and 16: theta = 95.8 degrees , according to DFT-calculations (B3LYP/6-311G**)), which was generated at room temperature by a valence isomerization/dehydrogenation (VID) reaction. HOMA and NICS indicate 92-98% retention of aromaticity of the highly distorted pyrene systems compared to planar pyrene. |
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