A family of unsymmetrical hydroxyl-substituted BEDT-TTF donors: syntheses, structures and preliminary thin film studies

Wang, Q, Zecchini, M, Wallis, JD ORCID: 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
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:
NumberType
10.1039/C5RA04568ADOI
Rights: © Royal Society of Chemistry 2015
Divisions: Schools > School of Science and Technology
Depositing User: EPrints Services
Date Added: 09 Oct 2015 09:56
Last Modified: 09 Jun 2017 13:14
URI: http://irep.ntu.ac.uk/id/eprint/5092

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