Wang, Q, Zecchini, M, Wallis, JD ORCID: https://orcid.org/0000-0001-7259-8783, Wu, Y, Rawson, JM and Pilkington, M, 2015. A family of unsymmetrical hydroxyl-substituted BEDT-TTF donors: syntheses, structures and preliminary thin film studies. RSC Advances, 5 (50), pp. 40205-40218. ISSN 2046-2069
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Abstract
Three new unsymmetrical hydroxyl-functionalized donors H1–H3 closely related to hydroxymethyl-BEDT-TTF have been synthesised and characterised. Cyclic voltammetry studies showed that the compounds exhibit reversible two one-electron redox processes typical for BEDT-TTF derivatives. X-ray diffraction studies of H1 and H2 reveal π-stacking interactions between pairs of donors that are organized into distinct H-bonded square motifs and DFT calculations indicate that the HOMO is located on the central 1,3-dithiole rings. Protection of the hydroxyl group with acetyl in 13 eliminates co-facial S...S interactions between the dimers to accommodate the bulkier side chains, but short edge-to-edge S...S contacts offer an alternative pathway for electron mobility. Chemical oxidation of H1 and HMET 2 with I2 afforded single crystals of two 1 : 1 charge transfer salts, 18 and 19. The molecules pack as dimers with close π-stacking interactions between pairs of radical cations whose crystal structures are further stabilized via an interplay of S...S and S...I contacts. Iodine-doped surface conducting polystyrene blend films of H3 deposited on a silica substrate exhibit quasiconducting properties, but afford no OFET response when fabricated into devices. Visible-NIR studies of a doped polystyrene blend film of H3 cast on a glass substrate show absorption bands at λ =9 50 and 3000 nm, consistent with mixed valence states due to the presence of charge-transfer species on the surface of the films.
Item Type: | Journal article |
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Publication Title: | RSC Advances |
Creators: | Wang, Q., Zecchini, M., Wallis, J.D., Wu, Y., Rawson, J.M. and Pilkington, M. |
Publisher: | Royal Society of Chemistry |
Date: | 2015 |
Volume: | 5 |
Number: | 50 |
ISSN: | 2046-2069 |
Identifiers: | Number Type 10.1039/C5RA04568A DOI |
Rights: | © Royal Society of Chemistry 2015 |
Divisions: | Schools > School of Science and Technology |
Record created by: | EPrints Services |
Date Added: | 09 Oct 2015 09:56 |
Last Modified: | 09 Jun 2017 13:14 |
URI: | https://irep.ntu.ac.uk/id/eprint/5092 |
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