Synthesis and Anion Binding Properties of a Novel Selectively Substituted Bipyrrole

Eduard Dolusic, Raoul Mens, Wim Dehaen

Research output: Contribution to conferencePoster

Abstract

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.
Original languageEnglish
PagesAbstracts, 7th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, December 2003, pp. 15-15
Number of pages1
Publication statusPublished - 2003
Event7th Sigma-Aldrich Organic Synthesis Meeting - Spa, Belgium
Duration: 4 Dec 2003 → …

Conference

Conference7th Sigma-Aldrich Organic Synthesis Meeting
CountryBelgium
CitySpa
Period4/12/03 → …

Keywords

  • bipyrrole
  • synthesis
  • Ullmann coupling reaction
  • 5 5'-diethoxycarbonyl-3 3'-di(n-hexyl)-2 2'-bipyrrole

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