Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection

Three bibrachial cyclobisintercaland-type macrocycles with a 2,6-naphthylene scaffold and pyrene, ferrocene, or primary amino groups in side chains were synthesized by a [2+2]-cyclocondensation of functionalized diethylenetriamine derivatives with naphthalene-2,6-dialdehyde, whereas their monobrachial counterparts were prepared by a [1+1]-cyclocondensation of polyamines with a corresponding dialdehyde building block. The pyrene-functionalized macrocycles are able to bind orthophthalate and terephthalate anions in aqueous medium, as monitored by the changes in their fluorescence (excimer or monomer) properties.