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Synthesis 1999; 1999(4): 565-567
DOI: 10.1055/s-1999-3453
short paper
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New Porphyrinoid Diimines by Cyclization of 1,9-Bis(5-formylpyrrol-2-yl)-dipyrrins with Arene-1,2-diamines and Hydrazines

Stephan Seggewies* , Thomas Schönemeier, Eberhard Breitmaier
  • *Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany
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Publication Date:
31 December 1999 (online)

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Four new porphyrinoid diimines 3, 4, 5 and 6 are synthesized from alkylated 1,9-bis(5-formylpyrrol-2-yl)dipyrrins 1 and diaminobenzidine 2a, hydrazine (2b), N,N′-diaminoguanidine (2c) and 3,4-diaminopyridine (2d). Macrocycles 4 and 5 resist oxidation with DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) to 18π or 22π aromatic systems, while 3 and 6 are readily obtained as aromatic macrocycles. From the latter, 6 exhibits deshielded protons outside and shielded NH protons inside due to 22π aromaticity.

dipyrrins - porphyrinoid diimines - porphyrinoid azines - 22π aromaticity - triaza[22]annulenes - "expanded texaphyrins" - NMR