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A compact tetrathiafulvalene-benzothiadiazole dyad and its highly symmetrical charge-transfer salt: Ordered donor π-stacks closely bound to their acceptors

AutorYan Geng; Pfattner, Raphael ; Campos, Antonio; Hauser, Jürg; Laukhin, Vladimir ; Puigdollers González, Joaquim; Veciana, Jaume ; Mas Torrent, Marta ; Rovira, Concepció ; Decurtins, Silvio; Liu, Shi-Xia
Palabras claveElectrical conductivity
Tetrathiafulvalene–benzothiadiazole
Donor–acceptor systems
Organic field-effect transistor
Charge transfer
Fecha de publicación2-jun-2014
EditorJohn Wiley & Sons
CitaciónChemistry - A European Journal 20(23): 7136- 7143 (2014)
ResumenA compact and planar donor-acceptor molecule 1 comprising tetrathiafulvalene (TTF) and benzothiadiazole (BTD) units has been synthesised and experimentally characterised by structural, optical, and electrochemical methods. Solution-processed and thermally evaporated thin films of 1 have also been explored as active materials in organic field-effect transistors (OFETs). For these devices, hole field-effect mobilities of μFE=(1. 3±0.5)×10-3 and (2.7±0.4)×10-3 cm2 V s-1 were determined for the solution-processed and thermally evaporated thin films, respectively. An intense intramolecular charge-transfer (ICT) transition at around 495 nm dominates the optical absorption spectrum of the neutral dyad, which also shows a weak emission from its ICT state. The iodine-induced oxidation of 1 leads to a partially oxidised crystalline charge-transfer (CT) salt {(1)2I3}, and eventually also to a fully oxidised compound {1I3} 1/2I2. Single crystals of the former CT compound, exhibiting a highly symmetrical crystal structure, reveal a fairly good room temperature electrical conductivity of the order of 2 S cm-1. The one-dimensional spin system bears compactly bonded BTD acceptors (spatial localisation of the LUMO) along its ridge. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
URIhttp://hdl.handle.net/10261/117448
DOI10.1002/chem.201304688
Identificadoresdoi: 10.1002/chem.201304688
issn: 1521-3765
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