Structure-Property Relationships for Potential Inversion from Electron Acceptors Based on Thiophene-Fused Triptycene Quinones, 1,4-Diketones and their Malononitrile Adducts

Stefan Warrington, Stephanie Montanaro, Mark R J Elsegood, Gary Nichol, Iain Wright

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
JournalChemistry - A European Journal
Early online date22 Mar 2024
DOIs
Publication statusE-pub ahead of print - 22 Mar 2024

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