Synthesis of Bisbenzyne Derivatives and their Organic Field Effect Transistors Application
| Autor: | Chao-Lin Wu, 吳昭霖 |
|---|---|
| Rok vydání: | 2010 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 98 Organic molecules have been giving the impression that the insulation material, but since Professor Hideki Shirakawa discovered conjugated organic molecules can also be conductive, the organic semiconductor materials have been widely studied. The organcic semiconductor material of pentacene derivatives have excellent electrical performance. However, poor solubility and stability of pentacene limit its application on the fabrication process. In this study, naphthalene and anthracene monomer for the molecular design of a series of ployacenes to improve solubility, crystalline properties, thermal stability, while in the main terminal to import aryl that could improve the crystallization of molecules in order to achieve good charge transfer characteristics. These organic transistors were synthesized by means of Diels-Alder reaction. In the synthetic methods, this study will use the Diels-Alder reaction replace thetraditional synthesis of polycyclic aromatic derivatives. The reason is Diels-Alder reaction could simplify reaction steps and improve the material yield, the addition that could increase reactive selectivity. In this work, according to different substituents an reactive conduction to choice different bisbenzyne precursors to achieve the synthesis of bisbenzyne, then using different dienophile substituents will be synthesized a series of organic transistors. The OTFT application potential of the transistor molecules was assessed from the photopysical properties, thermal stabilities and electrochemical behaviors. Photophysical properties of the fluorophors were characterized from UV-visible and Fluorescence spectra. Thermal properties of the pyrrole fluorophores were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Cyclic voltammetry (CV) was employed to investigate the electrochemical behaviors of these transistors. The results show that this type of transistor, the resonant length increases, the absorption and emission wavelength will have obvious red shift. In addition, thermal properties, these transistors C1 and C2 there were no obvious morphological change at 350 ℃, and the thermal decomposition temperature were up to 450 ℃. These result exhibits these transistors possess highly thermal stability. From the result of redox, these transistors have a hole transmission characteristics. HOMO levels of these transistors were estimated to be around 5.65~5.85eV, and the LUMO level were estimated to be around 2.1~ 2.8 eV. In this work, relationship between the chemical architecture and their electrooptical properties was also studied. In the HOMO level, the electron cloud will focus on molecular center, but when the LUMO level, then the electron cloud will distributed to the main part of binaphthalene or bianthracene, indicating that such material used in transistors, thecharge would move from one molecule’s center hopping to another’s molecule’s center, its main delivery centers charge will be based on polycyclic aromatic hydrocarbons as the main path, the outer ring is not aromatic participate in charge transfer. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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