Tetrachlorinated Tetraazaperopyrenes (TAPPs): Highly Fluorescent Dyes and Semiconductors for Air-Stable Organic n-Channel Transistors and Complementary Circuits
CHEMISTRY-A EUROPEAN JOURNAL
Authors: Martens, Susanne C.; Zschieschang, Ute; Wadepohl, Hubert; Klauk, Hagen; Gade, Lutz H.
Abstract
A range of 2,9-perfluoroalkyl-substituted tetraazaperopyrene (TAPP) derivatives (15) 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 14 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 69, 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 F=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 34 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.
Data on optical microscopy and vibrational modes in Diphenyl Dinaphthothienothiophene thin films
DATA IN BRIEF
Authors: Hattori, Yoshiaki; Kimura, Yoshinari; Yoshioka, Takumi; Kitamura, Masatoshi
Abstract
The thin-films of 2,9-diphenyl-dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DPh-DNTT) prepared by vacuum deposition was observed by the optical microsope. By applying the dark-field mode in observation and/or image processing after imaging appropriately, morphological structure with a resolution of a few nanometers height was visualized easily and quickly. The technique can be used in a similar to atomic force microscopy, which is commonly used for imaging surface morphology. Moreover, the vibrational modes of a DPh-DNTT molecule calculated by quantum chemistry program is described as well as the comparison of the experimental Raman spectra for identification. The presented data are produced as part of the main work entitled "The Growth Mechanism and Characterization of Few-layer Diphenyl Dinaphthothienothiophene Films Prepared by Vacuum Deposition" (Hattori et al., 2019). (C) 2019 The Author(s). Published by Elsevier Inc.