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Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts

journal contribution
posted on 2024-03-27, 14:51 authored by Stefan WarringtonStefan Warrington, Stephanie Montanaro, Mark ElsegoodMark Elsegood, Gary S Nichol, Iain A Wright
The synthesis and properties of a series of 11,11,12,12‐tetracyano‐9,10‐anthraquinodimethane (TCAQ) inspired electron acceptors based on thiophene‐fused quinone and triptycene motifs is presented. This has yielded insights into structure‐property relationships for establishing and modulating simultaneous two electron reduction processes in TCAQ analogues. These new compounds were synthesised using a Friedel‐Crafts acylation between triptycene and thiophene‐3,4‐dicarbonyl chloride. Isomeric para‐quinones featuring a [c]‐fused thiophene on one side and a β,β‐ or α,β‐fused triptycene on the other were isolated alongside a thiophene‐3,4‐diketone which bears two triptycene fragments. Knoevenagel condensation of these products with malononitrile produced a quinoidal bis(dicyanomethylene), an oxo‐dicyanomethylene and an acyclic bis(dicyanomethylene). This series of new electron accepting molecules has been studied using X‐ray crystallography and the implications of their 3D structures on NMR and UV/vis absorbance spectroscopy and cyclic voltammetry results have been ascertained with conclusions underpinned by computational methods.

Funding

3D-Localisation - Three Dimensionally Defined Non-Fullerene Acceptors

Engineering and Physical Sciences Research Council

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History

School

  • Science

Department

  • Chemistry

Published in

Chemistry – A European Journal

Publisher

Wiley

Version

  • AM (Accepted Manuscript)

Rights holder

© Wiley-VCH GmbH

Publisher statement

This is the peer reviewed version of the following article: Stefan Warrington, Stephanie Montanaro, Mark R. J. Elsegood, Gary S. Nichol, Iain A. Wright, Chem. Eur. J. 2024, e202400782, which has been published in final form at https://doi.org/10.1002/chem.202400782. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

Acceptance date

2024-03-21

Publication date

2024-03-22

Copyright date

2024

ISSN

0947-6539

eISSN

1521-3765

Language

  • en

Depositor

Dr Stefan Warrington. Deposit date: 26 March 2024

Article number

e202400782

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