Synthesis of Methylene-Bridged Bisnaphthalenes as Building Blocks for Push-Pull Substituted Pentacenes

The use of cross-coupling reactions for the synthesis of methylene-bridged bisnaphthalenes bearing two nitro groups on one naphthalene and two amino groups on the other has been investigated. A Hauser-Heck reaction was used to prepare the substituted naphthalene building blocks. It was not possible to install a transmetallating function in the benzylic position due to side reactions with the nitro and the amino groups. A successful Suzuki reaction was achieved using naphthyl trifluoroborates and bromomethyl naphthalenes. The resulting dinaphthyl methanes could be useful for the synthesis of push-pull substituted pentacenes.

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