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Synfacts 2006(9): 0897-0897  
DOI: 10.1055/s-2006-942035
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Redox-Active Triazacyclophane

Contributor(s): Timothy M. Swager, Wei Zhang
G. Hennrich, B. Alonso, A. Monge, E. Gutierrez-Puebla, A. M. Echavarren, B. Gómez-Lor*
Instituto de Ciencia de Materiales de Madrid; Institut Català d’lnvestigació Química; Universidad Autónoma de Madrid, Spain
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Publikationsdatum:
23. August 2006 (online)

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Significance

A high-yielding synthesis of a novel triazacyclophane based on the C 3-symmetric indole trimer 1 was reported, in which alkylation of 1 with tris(benzylbromide)benzene 2 in the presence of potassium hydroxide provided 3 in almost quantitative yield. X-ray structure analysis indicated that the oxidation product of cyclophane 3 is a dimeric radical cation (3)2 · +, with the positive charge delocalized within the dimeric structure. The observed shortening in the distance between the central rings of the triindole and the triphenylbenzene in the oxidized product suggested a through-space interaction. The UV/Vis spectrum was also indicative of the formation of a dimeric resonance-transfer complex.