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

Submitting author affiliation:
Kyoto University, Kyoto, Japan

Beilstein Arch. 2025, 202539. https://doi.org/10.3762/bxiv.2025.39.v1

Published 03 Jun 2025

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Abstract

Intramolecular oxidative fusion reaction of macrocyclic heteroaromatic arrays has provided strained polycyclic heteroaromatic macrocycles as promising functional molecules. In this study, we prepared an ortho-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.

Keywords: heterohelicene; intramolecular oxidative coupling; cyclophane; fluorescence

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Matsuo, Y.; Nakagawa, A.; Seki, S.; Tanaka, T. Beilstein Arch. 2025, 202539. doi:10.3762/bxiv.2025.39.v1

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