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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

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 simulta...

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Main Authors: Stefan Warrington, Stephanie Montanaro, Mark Elsegood, Gary S Nichol, Iain A Wright
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Published: 2024
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Online Access:https://hdl.handle.net/2134/25481620.v1
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author Stefan Warrington
Stephanie Montanaro
Mark Elsegood
Gary S Nichol
Iain A Wright
author_facet Stefan Warrington
Stephanie Montanaro
Mark Elsegood
Gary S Nichol
Iain A Wright
author_sort Stefan Warrington (9738227)
collection Figshare
description 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.
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spelling rr-article-254816202024-03-22T00:00:00Z Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts Stefan Warrington (9738227) Stephanie Montanaro (5783033) Mark Elsegood (1249893) Gary S Nichol (18257836) Iain A Wright (7409384) Chemical sciences Triptycene Anthraquinone Organic conductors Electron acceptors Potential inversion 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. 2024-03-22T00:00:00Z Text Journal contribution 2134/25481620.v1 https://figshare.com/articles/journal_contribution/Structure_property_relationships_for_potential_inversion_from_electron_acceptors_based_on_thiophene_fused_triptycene_quinones_1_4_diketones_and_their_malononitrile_adducts/25481620 CC BY-NC-ND 4.0
spellingShingle Chemical sciences
Triptycene
Anthraquinone
Organic conductors
Electron acceptors
Potential inversion
Stefan Warrington
Stephanie Montanaro
Mark Elsegood
Gary S Nichol
Iain A Wright
Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title_full Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title_fullStr Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title_full_unstemmed Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title_short Structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
title_sort structure‐property relationships for potential inversion from electron acceptors based on thiophene‐fused triptycene quinones, 1,4‐diketones and their malononitrile adducts
topic Chemical sciences
Triptycene
Anthraquinone
Organic conductors
Electron acceptors
Potential inversion
url https://hdl.handle.net/2134/25481620.v1