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

Autor: Warrington S; School of Chemistry, University of Edinburgh Joseph Black Building, David Brewster Road, Edinburgh, EH16 5PL, United Kingdom.; Department of Chemistry, Loughborough University, Epinal Way, Loughborough, Leicestershire, LE11 3TU, United Kingdom., Montanaro S; Department of Chemistry, Loughborough University, Epinal Way, Loughborough, Leicestershire, LE11 3TU, United Kingdom., Elsegood MRJ; Department of Chemistry, Loughborough University, Epinal Way, Loughborough, Leicestershire, LE11 3TU, United Kingdom., Nichol GS; School of Chemistry, University of Edinburgh Joseph Black Building, David Brewster Road, Edinburgh, EH16 5PL, United Kingdom., Wright IA; School of Chemistry, University of Edinburgh Joseph Black Building, David Brewster Road, Edinburgh, EH16 5PL, United Kingdom.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 May 28; Vol. 30 (30), pp. e202400782. Date of Electronic Publication: 2024 Apr 22.
DOI: 10.1002/chem.202400782
Abstrakt: 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.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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