(Oligo-)Thiophene Functionalized Tetraazaperopyrenes: Donor-Acceptor Dyes and Ambipolar Organic Semiconductors
Tetraazaperopyrenes (TAPPs) have been functionalized with thiophene and terthiophene units of different architecture resulting in a variety of organic donor−acceptor (D−A) compounds. The influence of the connection of the thiophenes to the TAPP core on their structural, photophysical and electrochemic...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
November 7, 2017
|
| In: |
The journal of organic chemistry
Year: 2017, Volume: 82, Issue: 23, Pages: 12492-12502 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.7b02286 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1021/acs.joc.7b02286 Verlag, Volltext: http://pubs.acs.org/doi/10.1021/acs.joc.7b02286 
|
| Author Notes: | Lena Hahn, André Hermannsdorfer, Benjamin Günther, Tobias Wesp, Bastian Bühler, Ute Zschieschang, Hubert Wadepohl, Hagen Klauk, and Lutz H. Gade |
| Summary: | Tetraazaperopyrenes (TAPPs) have been functionalized with thiophene and terthiophene units of different architecture resulting in a variety of organic donor−acceptor (D−A) compounds. The influence of the connection of the thiophenes to the TAPP core on their structural, photophysical and electrochemical properties has been studied in detail by a combination of X-ray crystallography, UV−vis and fluorescence spectroscopy as well as cyclic voltammetry, which allowed the establishment of structure−property relationships. The HOMO−LUMO gap is significantly decreased upon substitution of the TAPP core with electron-donating thiophene units, the extent of which is strongly influenced by the orientation of the thiophene units. The latter also crucially directs the molecular packing in the solid. Linkage at the α-position allows both inter- and intramolecular N···S interaction, whereas linkage in the β-position prevents intramolecular N···S interaction, resulting in a less pronounced conjugation of the TAPP core and the thiophene units. The new TAPP derivatives were processed as semiconductors in organic thin-film transistors (TFTs) that show ambipolar behavior. The insight into band gap and structure engineering may open up new possibilities to tailor the electronic properties of TAPP-based materials for certain desired applications. |
|---|---|
| Item Description: | Gesehen am 03.05.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.7b02286 |