由菲醌合成新菲系衍生物之研究

Synthesis of phenanthrene derivatives from 9,10-phenanthrenequinone

鄧宛容(Wan-Jung Teng)

指導教授 ： 吳吉輝

中原大學/理學院/化學研究所/碩士(2005年)

https://doi.org/10.6840/cycu200700051

摘要

中 文 摘 要

本論文進行了菲醌衍生物的合成，以9,10-phenanthrenequinone當起始物，採用aldol 縮合反應及 Wolff-Kishner還原反應合成出菲醌衍生物單體，再以溴、溴甲基和硼酯將它官能化，利用Suzuki偶聯反與Gilch反應，合成出兩種菲系高分子聚合物。以Suzuki反應出之聚合物為Poly(1.5-(Biphenyl-2,2’-diyl)-cis-bicyclo[3.3.0]octane) (聚合物2)，吸收光譜在312 nm，螢光放射波長在414 nm，電激發光波長為431nm， CIE 座標為(0.22, 0.23) ，能帶為3.54eV。以Gilch反應合成出之聚合物為Poly(5,5’-vinylene-(1.5-(biphenyl-2,2’-diyl)-cis-bicyclo[3.3.0]octane)) (聚合物1)，吸收光譜在321nm，螢光放射波長在484 nm，電激發光波長在502 nm，CIE 座標為 (0.27, 0.64)。兩支高分子聚合物均具有立體雙戊環的構型，由於Gilch反應之聚合物鏈上多一乙烯基，乙烯基為拉電子基，造成較低能帶 (3.28eV)，因此做為聚合物主鏈的自由度較高，分子鏈也較柔軟，成膜時之溶解度較好。

關鍵字

電激發光 ； 菲醌 ； 光激發光

並列摘要

Abstract
Phenanthrene is an important chemical of nature materials. In this study, two types of phenanthrene derivatives were synthesized by Aldol condensation and Wolff-Kishner reduction methods. After bromination and boration of these two phenanthrene derivatives, Poly (1,5-(Biphenyl-2,2’-diyl)-cis-bicyclo-octane) (polymer2) and Poly (5,5’-vinylene-(1.5-(biphenyl-2,2’-diyl)-cis-bicyclo-octane)) (polymer1) conjugated polymers were polymerized by Suzuki cross coupling reaction and Glich dehalogenation reaction. The UV-Vis absorption, PL (Photoluminescence) and EL (Electroluminescence) spectra of polymer2 are 312 nm, 414 nm and 431 nm repectively. The CIE coordinate and band gap of polymer2 is (0.22, 0.23) and 3.54eV respectively, so it is a blue emission polymer. The UV-Vis absorption, PL and EL spectra of polymer1 are 321 nm, 484 nm and 502 nm. repectively. The CIE coordinate of polymer1 is (0.27, 0.64), so it is a green emission polymer. Because of the vinyl-group in main chain of polymer1, that makes polymer1 has more soluble and less band gap(3.28eV) than that of polymer2.

並列關鍵字

phenanthrene ； electroluminescence ； photoluminescence

參考文獻

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第五章、参考文獻