Polyphenylene dendrimers: From three-dimensional to two-dimensional structures

Article abstract of DOI:10.1002/anie.199706311

An elegant route to aromatic hydrocarbon dendrimers, such as 1 with pentaphenylbenzene units, and to extremely large polybenzenoid hydrocarbons is based on Diels-Alder cycloadditions of 3,4-bis-[4-(triisopropylsilylethynyl)phenyl]-2,5-diphenyl-cyclopenta-2,4-dien one and aromatic oligoethynyl compounds such as 3,3',5,5'-tetraethynylbiphenyl. The type of linkage and the high packing density of the benzene rings facilitate the cyclodehydrogenalion of appropriate dendrimeric subunits to yield planar disks.