Building Blocks for the Construction of Large Chloro-Functionalized, Hexagonal Oligophenylene Cycles

The synthesis of a variety of kinked oligophenylene building blocks is described. The synthetic strategy is repetitive, utilizes the Suzuki cross-coupling protocol, and involves potentially bifunctional building blocks (modules) which carry one functional group for coupling and one group which serves as place holder. After the coupling, the placeholder is converted into a coupling functionality for the next growth step. The building blocks also carry chloro-substituents which are unaffected by all transformations. For one of the large building blocks it is shown that it actually can be cyclized into an oligophenylene macrocycle with a chloro-substituent at each corner and a pair of hexyl chains at each side.