Theoretical study on the CH?NC hydrogen bond interaction in thiophene-based molecules

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• 作者：Regina Luschtinetz^a ; ^{regina.luschtinetz@chemie.tu-dresden.de} ; Sibylle Gemming^b ; ^{s.gemming@hzdr.de} ; Gotthard Seifert^a ; ^{gotthard.seifert@chemie.tu-dresden.de}
• 关键词：Intermolecular interaction ; Hydrogen bond ; Thiophene ; Quantum-mechanical calculations ; Organic semiconducting material
• 刊名：Computational and Theoretical Chemistry
• 出版年：2013
• 出版时间：1 February, 2013
• 年：2013
• 卷：1005
• 期：Complete
• 页码：45-52
• 全文大小：1168 K

文摘

Results on a detailed investigation of the CH?NC hydrogen bond interaction in functional thiophene-based molecules are presented by employing quantum-mechanical ab initio and DFT-based calculations. Dimers of 1-cyano-thiophene are studied to evaluate the influence of the computational method, of the chosen basis set and of substitution in 3-position on the structure and stability of the hydrogen bond. Furthermore, we focus on the intermolecular hydrogen bond in a chain of ¦Á,¦Ø-dicyano-¦Â,¦Â¡ä-dibutylquarterthiophene (DCNDBQT) molecule, which was found to be a promising organic semiconducting material for thin-film organic field-effect transistors. In particular, the intermolecular structure and the electronic properties of the material are determined employing the efficient SCC-DFTB method. We demonstrate the highly local character of the hydrogen and found that the weak CH?NC interaction links the molecules into extended ribbons perpendicular to the support.