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. (C) 2008 Elsevier Ltd. All rights reserved.