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Core‐Brominated Tetraazaperopyrenes as n‐Channel Semiconductors for Organic Complementary Circuits on Flexible Substrates
Author(s) -
Geib Sonja,
Zschieschang Ute,
Gsänger Marcel,
Stolte Matthias,
Würthner Frank,
Wadepohl Hubert,
Klauk Hagen,
Gade Lutz H.
Publication year - 2013
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201203600
Subject(s) - homo/lumo , materials science , bromine , cyclic voltammetry , density functional theory , thin film transistor , organic semiconductor , substrate (aquarium) , transistor , electrochemistry , optoelectronics , nanotechnology , organic chemistry , chemistry , computational chemistry , molecule , layer (electronics) , electrode , voltage , physics , oceanography , quantum mechanics , geology , metallurgy
Organic thin‐film transistors (TFTs) are prepared by vacuum deposition and solution shearing of 2,9‐bis(perfluoroalkyl)‐substituted tetraazaperopyrenes (TAPPs) with bromine substituents at the aromatic core. The TAPP derivatives are synthesized by reacting known unsubstituted TAPPs with bromine in fuming sulphuric acid, and their electrochemical properties are studied in detail by cyclic voltammetry and modelled with density functional theory (DFT) methods. Lowest unoccupied molecular orbital (LUMO) energies and electron affinities indicate that the core‐brominated TAPPs should exhibit n‐channel semiconducting properties. Current‐voltage characteristics of the TFTs established electron mobilities of up to μ n = 0.032 cm 2 V −1 s −1 for a derivative which was subsequently processed in the fabrication of a complementary ring oscillator on a flexible plastic substrate (PEN).