- Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications
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A series of tetra- and octa-substituted hexa-cata-hexabenzocoronenes (cata-HBCs) were synthesized from tetraryl olefins via iodine- and iron chloride-catalyzed oxidative cyclodehydrogenation reactions. The substitutions on the periphery of the parent HBC serve to modify the photophysical properties, highest occupied molecular orbital-lowest unoccupied molecular orbital gaps, and thermal stabilities of the respective derivatives. The crystal structures were determined to display multiple twists in the framework, resulting in different packing motifs depending on the position, type, and number of functional groups on the hexabenzocoronene framework. Nearly perfect co-facial packing to marginally or extensively shifted co-facial stacks were obtained due to substitution. The single crystals of parent HBC were used to fabricate single-crystal field-effect transistors, from which the highest p-channel mobility of 0.51 cm2 V-1 s-1 was measured. Thin-film transistors of selected HBCs were also prepared, and 0.61 cm2 V-1 s-1 was obtained for MeHBC-2. These results attest the potential of these materials as semiconducting materials.
- Kumar, Sushil,Pola, Someshwar,Huang, Chih-Wei,Islam, Md. Minarul,Venkateswarlu, Samala,Tao, Yu-Tai
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- Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: Straightforward access to 1,3,5-triarylbenzenes under mild conditions
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An efficient triple condensation reaction of aryl methyl ketones catalyzed by ethylenediamine and trifluoroacetic acid was reported. A broad scope of 1,3,5-triarylbenzenes was obtained in good to excellent yields. The reaction provides a novel and practical approach to access organic materials of polycyclic aromatic hydrocarbons under mild conditions.
- Zhang, Shao-Liang,Xue, Zhao-Feng,Gao, Ya-Ru,Mao, Shuai,Wang, Yong-Qiang
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- Molecular wires from contorted aromatic compounds
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(Figure Presented) In a twist: A design strategy for molecule-based electronic materials using aromatic compounds with a nonplanar core is presented. A new class of hexabenzocoronene is put forth that has its core severely distorted out of planarity into a corrugated structure. When substituted with four alkoxy side chains, this material self-assembles into infinitely long columns through stacking (see picture) and acts as an active layer in field-effect transistors.
- Xiao, Shengxiong,Myers, Matthew,Miao, Qian,Sanaur, Sebastien,Pang, Keliang,Steigerwald, Michael L.,Nuckolls, Colin
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p. 7390 - 7394
(2007/10/03)
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