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. 2016 Jun 22;138(24):7540-3.
doi: 10.1021/jacs.6b04941. Epub 2016 Jun 9.

Template Synthesis of Decaphyrin without Meso-Bridges: Cyclo[10]pyrrole

Tetsuo Okujima  1 , Chie Ando  1 , Saurabh Agrawal  2 , Hiroki Matsumoto  1 , Shigeki Mori  3 , Keishi Ohara  1 , Ichiro Hisaki  4 , Takahiro Nakae  1 , Masayoshi Takase  1 , Hidemitsu Uno  1 , Nagao Kobayashi  2
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Template Synthesis of Decaphyrin without Meso-Bridges: Cyclo[10]pyrrole

Tetsuo Okujima et al. J Am Chem Soc. .

Abstract

An acenaphthylene-fused cyclo[10]pyrrole 1b was selectively synthesized via an oxidative coupling reaction of the corresponding 2,2'-bipyrrole with the appropriate dianion template, croconate anion. The structure of 1b as the isolated largest cyclo[n]pyrrole was elucidated by X-ray crystallographic analysis. The absorption spectrum exhibited a markedly red-shifted, intensified L band at 1982 nm, which was interpreted by application of Michl's perimeter and Gouterman's 4-orbital models, supported by magnetic circular dichroism (MCD) data and theoretical calculations.

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