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

## TL;DR

Scientists synthesized a new complex molecule by fusing heteroaromatic rings, revealing its structure and optical properties.

## Contribution

A new macrocyclic heteroarene incorporating aza[5]helicene was synthesized and structurally confirmed.

## Key findings

- An o-phenylene-pyrrole-thiophene icosamer was synthesized as the largest cyclic array in the series.
- Oxidative fusion with PIFA produced a cyclophane-type aza[5]helicene macrocycle confirmed by X-ray diffraction.
- The optical properties of the macrocycle were studied in detail.

## 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 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.