Enhanced Layered-Herringbone Packing due to Long Alkyl Chain Substitution in Solution-Processable Organic Semiconductors
| Autor: | Hiromi Minemawari, Satoru Inoue, Yukihiro Shimoi, Reiji Kumai, Tatsuo Hasegawa, Toshikazu Yamada, Mutsuo Tanaka, Seiji Tsuzuki |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Chemistry General Chemical Engineering 02 engineering and technology General Chemistry Crystal structure 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Solvent Organic semiconductor Crystallography Chain (algebraic topology) Intermolecular interaction Materials Chemistry 0210 nano-technology Alkyl |
| Zdroj: | Chemistry of Materials. 29:1245-1254 |
| ISSN: | 1520-5002 0897-4756 |
| DOI: | 10.1021/acs.chemmater.6b04628 |
| Popis: | Herein, we report the stabilization and modulation of layered-herringbone (LHB) packing, which is known to afford high-performance organic thin-film transistors, based on crystal structure analyses and calculations of intermolecular interaction energies for alkyl-substituted organic semiconductor (OSC) crystals. We systematically investigated the alkyl chain-length dependence of the crystal structures, solvent solubilities, and thermal characteristics for three series of symmetrically and asymmetrically alkyl-substituted benzothieno[3,2-b][1]benzothiophenes (BTBTs). All the series exhibit LHB packing when the BTBTs are substituted with relatively long alkyl chains (−CnH2n+1), i.e., n ≥ 4 for monoalkylated, n ≥ 6 for dialkylated, and n ≥ 5 for phenyl-alkylated BTBTs. LHB packing is also evident in the nonsubstituted and diethyl-substituted BTBTs, although those substituted with short alkyl chains generally did not feature LHB packing because of their lack of interchain ordering. The density functional theo... |
| Databáze: | OpenAIRE |
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