Anion-Induced Synthesis and Combinatorial Selection of Polypyrrolic Macrocycles

✍ Scribed by Evgeny A. Katayev; G. Dan Pantos; Marina D. Reshetova; Victor N. Khrustalev; Vincent M. Lynch; Yuri A. Ustynyuk; Jonathan L. Sessler

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 359 KB
• Volume: 117
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200502393

✦ Synopsis

One of the current challenges in the area of supramolecular chemistry involves the preparation of anion receptors with high selectivity for specifically targeted anionic guests. [1] Such systems could have an important role to play in a variety of applications, including sensing, analysis, waste remediation, and drug development. One approach for designing highly efficient anion receptors is to use anion-templated strategies to produce macrocyclic systems whose geometry is complementary to that of the targeted guests. [2] Although this concept has yet to be extensively exploited in the case of pyrrole-based systems, recently we prepared cyclo[n]pyrroles through self-coupling of bipyrroles under oxidative conditions in the presence of suitable anionic templates. In earlier work, we found that bipyrrole-amide-derived catenanes [3] and the Schiff base expanded porphyrin 1 ("USAphyrin") [4] could be synthesized using anion-templated processes. Finally, in the case of the 2,6-diamidopyridine-containing system 2, we noted that improved yields were seen when the initial macrocycle-forming reaction was carried out in the presence