Nonplanar aromatic compounds. 9. Synthesis, structure, and aromaticity of 1:2,13:14-dibenzo[2]paracyclo[2](2,7)- pyrenophane-1,13-diene

Baozhong Zhang; Gregory P Manning; Michał A Dobrowolski; Michał K Cyrański; Graham J Bodwell

doi:10.1021/ol702703b

Nonplanar aromatic compounds. 9. Synthesis, structure, and aromaticity of 1:2,13:14-dibenzo[2]paracyclo[2](2,7)- pyrenophane-1,13-diene

Org Lett. 2008 Jan 17;10(2):273-6. doi: 10.1021/ol702703b. Epub 2007 Dec 19.

Authors

Baozhong Zhang¹, Gregory P Manning, Michał A Dobrowolski, Michał K Cyrański, Graham J Bodwell

Affiliation

¹ Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7.

PMID: 18088135
DOI: 10.1021/ol702703b

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.