Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an -phenylene-pyrrole-thiophene icosamer.

Beilstein J Org Chem

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, Japan.

Published: July 2025


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Article Abstract

The intramolecular oxidative fusion reaction of macrocyclic heteroaromatic arrays has provided strained polycyclic heteroaromatic macrocycles as promising functional molecules. In this study, we prepared an -phenylene-pyrrole-thiophene hybrid icosamer, as the largest cyclic array in the series. The oxidative fusion reaction with [bis(trifluoroacetoxy)iodo]benzene (PIFA) afforded a cyclophane-type aza[5]helicene-incorporated macrocycle, the structure of which was unambiguously revealed by X-ray diffraction analysis. Its optical properties have been investigated in detail.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12320735PMC
http://dx.doi.org/10.3762/bjoc.21.119DOI Listing

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