Extended and Modulated Thienothiophenes for Thermally Durable and Solution-Processable Organic Semiconductors
| Autor: | Satoru Inoue, Kazuo Takimiya, Tatsuo Hasegawa, Yuichi Sadamitsu, Shoji Shinamura, Shunto Arai, Sachio Horiuchi, Makoto Yoneya |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Materials science General Chemical Engineering Benzothiophene 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Organic semiconductor chemistry.chemical_compound Crystallography chemistry Materials Chemistry Thiophene Phenyl group Molecule Thermal stability Solubility 0210 nano-technology Alkyl |
| Zdroj: | Chemistry of Materials. 30:5050-5060 |
| ISSN: | 1520-5002 0897-4756 |
| DOI: | 10.1021/acs.chemmater.8b01339 |
| Popis: | Herein, we report the rational design of practical small-molecule organic semiconductors based on a π-electron skeleton of benzothieno[3,2-b]naphtho[2,3-b]thiophene (BTNT) whose layered herringbone (LHB) packing is intentionally modulated by the designated asymmetric substitutions with the phenyl group and normal alkyl chains. The thermal stability of the hybrid BTNT core is high enough, as it lies between those of dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT) and benzothieno[3,2-b]benzothiophene (BTBT), although the solvent solubility for the substituted BTNT at ordinary 2,8-substituting positions by the alkyl chain and phenyl group remains extremely low. We show in the BTBT and BTNT derivatives that the tuning of the substituting position works to slightly bend the rodlike organic semiconductor molecules and thus to decrease the cohesive energy of the crystals with retention of the bilayer-type herringbone (b-LHB) packing for the asymmetric rodlike molecules. This modification eventually leads t... |
| Databáze: | OpenAIRE |
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