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Tetrachlorinated Tetraazaperopyrenes (TAPPs): Highly Fluorescent Dyes and Semiconductors for Air‐Stable Organic n‐Channel Transistors and Complementary Circuits
Author(s) -
Martens Susanne C.,
Zschieschang Ute,
Wadepohl Hubert,
Klauk Hagen,
Gade Lutz H.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103158
Subject(s) - electroluminescence , thiophene , cyclic voltammetry , materials science , substrate (aquarium) , fluorescence , homo/lumo , organic semiconductor , thin film transistor , electrochemistry , chemistry , photochemistry , optoelectronics , organic chemistry , molecule , nanotechnology , electrode , oceanography , physics , layer (electronics) , quantum mechanics , geology
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 cm 2 V −1 s −1 and an on/off current ratio of >10 6 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.