Synthesis and Anion Binding Properties of a Novel Selectively Substituted Bipyrrole

Bipyrroles are products with a broad spectrum of applications, among them the synthesis of higher cyclic oligopyrroles, including corroles, sapphyrins, porphycenes and new classes of compounds, such as cyclo[8]pyrrole. A number of synthetic procedures have recently been developed to obtain these useful synthons, albeit with varying succcess and usually in a rather low yield. In this work we present an improved synthesis of 5, 5'-diethoxycarbonyl-3, 3'-di(n-hexyl)-2, 2'-bipyrrole, starting with derivatizing pyrrole and finally making the pyrrole-pyrrole link via an Ullmann coupling reaction. All steps have been optimised to give rather high yields and attempts to scale up the synthesis (10+ gram scale) are in progress. Along with the synthesis, the results of binding studies of a number of anions with the bipyrroles, using UV spectrophotometry, are presented in the poster.