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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Single-molecule nanosized polycyclic aromatics with alternant five- and six-membered rings: synthesis and optical
Wei Zhang1, Xiao-Yu Cao, Hong Zi
1The Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Abstract:
[structure: see text] A synthetic protocol for a novel family of symmetric polycyclic aromatics with a benzene or cyclooctatetraene (COT) ring as the core and alternant fused benzene and cyclopentadiene rings as branches has been developed. The TiCl(4)-promoted cyclizations construct both planar trimers and tubelike tetramers via the "in situ" generation of the benzene or COT skeleton. The structures of 6b, 7a, 7b, and 10 have been characterized by (1)H and (13)C NMR spectra and MALDI-TOF mass spectroscopy. These polycyclic aromatics also exhibit interesting optical properties.
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