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

Geng, Yan; Pfattner, Raphael; Campos, Antonio; Hauser, Jürg; Laukhin, Vladimir; Puigdollers, Joaquim; Veciana, Jaume; Mas-Torrent, Marta; Rovira, Concepció; Decurtins, Silvio; Liu, Shi-Xia (2014). A Compact Tetrathiafulvalene-Benzothiadiazole Dyad and Its Highly Symmetrical Charge-Transfer Salt: Ordered Donor π-Stacks Closely Bound to Their Acceptors. Chemistry - a European journal, 20(23), pp. 7136-7143. Wiley-VCH 10.1002/chem.201304688

[img] Text
7136_ftp.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (626kB) | Request a copy

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 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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Geng, Yan; Hauser, Jürg; Decurtins, Silvio and Liu, Shi-Xia

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Silvio Decurtins

Date Deposited:

25 Mar 2015 14:19

Last Modified:

25 Mar 2015 23:31

Publisher DOI:

10.1002/chem.201304688

BORIS DOI:

10.7892/boris.65762

URI:

https://boris.unibe.ch/id/eprint/65762

Actions (login required)

Edit item Edit item
Provide Feedback