A Compact Tetrathiafulvalene-Benzothiadiazole Dyad and Its Highly Symmetrical Charge-Transfer Salt: Ordered Donor pi-Stacks Closely Bound to Their Acceptors

作者：Geng Yan; Pfattner Raphael; Campos Antonio; Hauser Juerg; Laukhin Vladimir; Puigdollers Joaquim; Veciana Jaume; Mas Torrent Marta^*; Rovira Concepcio; Decurtins Silvio; Liu Shi Xia

来源：Chemistry - A European Journal, 2014, 20(23): 7136-7143.

DOI：10.1002/chem.201304688

• charge transfer
• donor-acceptor systems
• electrical conductivity
• organic field-effect transistor
• tetrathiafulvalene-benzothiadiazole

A 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 FE=(1.3 +/- 0.5)x10-3 and (2.7 +/- 0.4)x10-3cm2Vs-1 were determined for the solution-processed and thermally evaporated thin films, respectively. An intense intramolecular charge-transfer (ICT) transition at around 495nm 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 2Scm-1. The one-dimensional spin system bears compactly bonded BTD acceptors (spatial localisation of the LUMO) along its ridge.

• 出版日期2014-6-2