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Synfacts 2011(9): 0957-0957  
DOI: 10.1055/s-0030-1261022
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Large PAHs with Small HOMO-LUMO Gaps

Contributor(s): Timothy M. Swager, Olesya Haze
T.-A. Chen, R.-S. Liu*
National Tsing-Hua University, Hsinchu, Taiwan
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Bis(aryl)diynes undergo PtCl2-catalyzed two-fold aromatization followed by a DDQ oxidation to give polycyclic aromatic hydrocarbons (PAHs) 1-4 in excellent yield. Extended PAH 5 was prepared from the corresponding bis(aryl)diyne with the use of ICl to effect the aromatization.