Tetrachlorinated Tetraazaperopyrenes (TAPPs) highly fluorescent dyes and semiconductors for air-stable organic n-channel transistors and complementary circuits Susanne C. Martens, Ute Zschieschang, Hubert Wadepohl, Hagen Klauk and Lutz H. Gade 

Erscheinungsform: Aufsatz
Autor/Urheber:
  • Martens, Susanne
Beteiligte:
Umfang: 12
Anmerkungen: Version of record online: 22 February 2012
Gesehen am 10.10.2018
Identifikatoren/​Sonstige Nummern: 1581726929 [PPN]
In: Weinheim : Wiley-VCH, 1995 18(2012), 12, Seite 3498-3509 volume:18 year:2012 number:12 pages:3498-3509 extent:12
Inhalt:
  • A range of 2,9-perfluoroalkyl-substituted tetraazaperopyrene (TAPP) derivatives (1-5) was synthesised by reacting 4,9-diamino-3,10-perylenequinone diimine (DPDI) with the corresponding carboxylic acid chloride or anhydride in the presence of a base. The reaction of compounds 1-4 with dichloroisocyanuric acid (DIC) in concentrated sulphuric acid resulted in the fourfold substitution of the tetraazaperopyrene core, yielding the 2,9-bisperfluoroalkyl-4,7,11,14-tetrachloro-1,3,8,10-tetraazaperopyrenes 6-9, respectively. The optical and electrochemical data demonstrate the drastic influence of the core substitution on the properties. All compounds are highly luminescent (fluorescence quantum yields of up to Φ=0.8). The LUMO energies of the tetrachlorinated TAPP derivatives (determined by cyclic voltammetry and computed by DFT calulations) were found to be below −4 eV. In the course of this work the performance of TAPP derivatives in organic thin-film transistors (TFTs) was investigated, and their n-channel characteristics with field-effect mobilities of up to 0.14 cm2 V−1 s−1 and an on/off current ratio of >106 were confirmed. Long-term stabilities of 3-4 months under ambient conditions of the devices were established. Complementary inverters and ring oscillators with n-channel TFTs based on compound 8 and p-channel TFTs based on dinaphtho-[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT) were fabricated on a glass substrate.
URL: http://dx.doi.org/10.1002/chem.201103158
Weiter im Partnersystem: https://swb.bsz-bw.de/DB=2.1/PPNSET?PPN=1581726929
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