# Polyaromatic Cyclophanes Design and their Related Optical Properties

**Authors:** Oumou Diallo, Jean‐Frédéric Audibert, Isabelle Leray, David Kreher, Guillaume H. V. Bertrand

PMC · DOI: 10.1002/open.202400207 · ChemistryOpen · 2024-12-04

## TL;DR

This paper describes the synthesis of polyaromatic cyclophanes and their optical properties, showing how their structure affects fluorescence and exciplex behavior.

## Contribution

A new synthetic approach to polyaromatic cyclophanes and their systematic photophysical characterization in different environments.

## Key findings

- Cyclophanes exhibit larger Stokes shifts and intramolecular exciplex behavior compared to non-cyclophane analogs.
- Photophysical properties of cyclophanes are solvent-dependent and consistent between solution and polystyrene films.
- Different synthetic methods yield cyclophane structures with distinct optical characteristics.

## Abstract

In this article, we present several organic synthetic way to synthesize a family of five polyaromatic molecules based on a cyclophane core. Our strategies revolves around palado‐catalyzed substitution on a [2.2]paracyclophane (pCp) building block. Direct formation of a cyclophane was also employed for two molecules. The polyaromatic nature of the cyclophane library we synthetized made them good fluorophores candidate, we hence performed full photophysical characterization (Absorption, Emission, TCSPC) in different solvent as well as embed in polystyrene films. We evaluate how the cyclophane moiety influence their photo physical properties compared to their corresponding homologues without pCp core, demonstrating greater stoke shift and intramolecular exciplex behavior. The general behavior among cyclophanes was also compared and show solvent dependent properties as well as consistency of the photophysics between toluene and polystyrene matrix.

This Study present the synthesis of polyaromatic cyclophane via different organic pathways. We performed a systematic photophysics study in solution (DCM and Toluene) as well as embed in polystyrene films. This allowed us to put forward the influence of the cyclophane ring on the photophysics properties; especially large stokes shift, intramolecular exciplex behavior and solvent dependent decay time.

## Linked entities

- **Chemicals:** Toluene (PubChem CID 1140)

## Full-text entities

- **Chemicals:** polystyrene (MESH:D011137), toluene (MESH:D014050), Polyaromatic Cyclophanes (-), [2.2]paracyclophane (MESH:C515344)

## Full text

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## Figures

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## References

45 references — full list in the complete paper: https://tomesphere.com/paper/PMC11973505/full.md

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Source: https://tomesphere.com/paper/PMC11973505