Facile syntheses of quater-, penta-, and sexipyrroles
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Updated: Aug 18, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Jonathan L Sessler1, Apolonio Aguilar, David Sanchez-Garcia
1Department of Chemistry and Biochemistry, Institute for Cellular and Molecular Biology, The University of Texas, Austin, 78712-0165, USA. sessler@mail.utexas.edu
Abstract:
alpha,alpha-Linked oligopyrroles are attractive precursors for both expanded porphyrin and conducting polymer chemistry. We demonstrate facile methods for synthesizing quater-, penta-, and sexipyrroles from more readily available bi- and terpyrrole intermediates. These products demonstrate stability in their brightly colored oxidized forms, while reduction using borohydride reagents gives the corresponding all-pyrrole oligomers, which oxidize readily in air. The oxidized quater- and sexipyrroles were characterized by single-crystal X-ray diffraction analysis.
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