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The functionalisation of the hinge region in a molecular tweezer molecule showing a strong binding to explosives is presented. Two versatile functional groups are introduced, a carboxylic acid and a bromine atom. [Copyright &y& Elsevier]

The preparative use of the reaction between tris(2,6-dimethoxyphenyl)carbenium tetrafluoroborate and excess of an arylamine such as 4-methylaniline or 4-bromoaniline to yield firstly the aryl functionalised acridinium derivatives and then further in situ reaction to yield the desired functionalised triangulenium salts was found to be problematic. A preparative route for the triangulenium salts is presented along with a demonstration of the further derivatisation by standard Suzuki coupling reaction. [Copyright &y& Elsevier]