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Rodlike Tetracene Derivatives
Author(s) -
Roth Michael,
Ahles Marcus,
Gawrisch Christian,
Schwalm Thorsten,
Schmechel Roland,
Melzer Christian,
von Seggern Heinz,
Rehahn Matthias
Publication year - 2017
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.201702382
Subject(s) - tetracene , materials science , halogen , thiophene , halogenation , aryne , ionization energy , crystallization , ionization , chemistry , photochemistry , anthracene , organic chemistry , alkyl , ion
Efficient and versatile synthetic access to rodlike tetracene derivatives was developed by means of Diels–Alder cycloaddition, halogenation, halogen–metal exchange, and transition metal mediated coupling reactions. Herein, the synthesis and structural, electrical, and charge‐transport properties of three of the resulting materials, namely, 2‐(tetracen‐2‐yl)tetracene, 1,4‐bis(2‐tetracenyl)benzene, and 2,5‐bis(2‐tetracenyl)thiophene, are presented. Good crystallization behavior on SiO 2 substrates, narrowing of the bandgap by 0.2 eV, and a decrease of the ionization potential of more than 0.5 eV compared to tetracene were observed. Charge‐carrier field‐effect mobilities on the order of 10 −1 cm 2 V −1 s −1 , on/off ratios of 10 5 , and threshold voltages V th <15 V were found in thin‐film organic field‐effect transistors prepared by standard high‐vacuum deposition techniques.