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 SiO2 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 cm2 V-1 s-1 , on/off ratios of 105 , and threshold voltages Vth <15 V were found in thin-film organic field-effect transistors prepared by standard high-vacuum deposition techniques.
Keywords: C−C coupling; acenes; charge-carrier mobility; semiconductors; thin layers.
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