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Design, Synthesis and Characterization of Novel Functional Organic Molecules Containing Acetylene

Author: LiuYu
Tutor: JiShunJun
School: Suzhou University
Course: Organic Chemistry
Keywords: 1,8-Naphthalimide derivatives Carbazole derivatives Sonogashira coupling reaction Mult-branch Ethyne-linked Ion recognition
CLC: O621.13
Type: Master's thesis
Year: 2009
Downloads: 104
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Abstract


Organic electroluminescent materials have attracted much attention in the research of optoelectronic information materials for the various advantages compared with inorganic light–emitting diodes. This thesis contains three parts, which mainly described the Synthesis of compounds containing Acetylene, and investigated the ions recognition properties of the terpyridine derivatives.In the first part a series of novel“ethyne-linked”compounds containing carbazole and 1,8-naphthalimide groups have been synthesized by Pd/Cu catalyzed Sonogashira reaction. These compounds were fully characterized by means of FT-IR, 1H NMR, 13C NMR, and HRMS. The UV-vis absorption spectra and Photoluminescence emission spectra of these compounds were investigated, their maximum UV-vis absorptions wavelength ranges from 393-435 nm, and the maximum emission peaks ranges from 544-560 nm,these properties implied that these compounds might be used as a blue-green light-emitting material. We studied their thermal and electrochemical properties, all the results indicated that these synthesized compounds were of high thermal stabilities, the HOMO levels were near the most widely used hole-transport material NPB, therefore, these compounds might be used as hole-transporting materials in OLEDs.In the second part a series of novel mult-branch“ethyne-linked”compounds have been synthesized by Pd/Cu catalyzed Sonogashira reaction. These compounds were fully characterized by means of FT-IR, 1H NMR, 13C NMR, and HRMS. The UV-vis absorption spectra and Photoluminescence emission spectra of these compounds were investigated, their maximum UV-vis absorptions wavelength ranges from 364-450 nm, and the maximum emission peaks ranges from 418-634 nm. We studied their thermal and electrochemical properties, all the results indicated that these synthesized compounds were of high thermal stabilities. These compounds can be applied as good dopant emitter with hole-transporting in OLEDs.In the third part a novel compound containing triphenylamine and 2,2’:6’,2’’-terpyridine group was synthesized via Suzuki cross-coupling, bearing the terpyridine as receptor. The recognition properties of this compound on transition metal ions were carefully investigated, which exhibited high sensitivity for sensing Co2+ in a large scale. For complexation ratio between ligand and Co2+ ion, we carried out Job plot experiment by varying the concentrations of both compound and Co2+ ion. The maximum point at the mole fraction of 0.67 indicates that a typical 2:1 (ligand:metal) complexation performs in this case.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Theory of organic chemistry,physical organic chemistry > Organic Chemistry Structure Theory
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