Title: 含有9,9’-螺結雙茀結構聚奎碄的合成與研究
Synthesis and Characterization of Polyquinoline Containing 9,9’-spirobifluorene
Authors: 江志隆
Chi-Long Chiang
Ching-Fong Shu
Keywords: Friedländer 縮合反應;9,9’-螺結雙茀;聚奎琳;Friedländer condensation;9,9’-spirobifluorene;Polyquinolines
Issue Date: 2000
Abstract: 本論文討論以Friedländer condensation 合成出主鏈含有9,9’-螺結雙茀結構的聚奎琳高分子。在這螺結體中,雙茀的共軛架構被一個四級碳以σ鍵方式連結而相互垂直,可增加高分子的溶解度以及加強分子鏈的剛硬度,導致於提高高分子的熱穩定性。進一步對探討其光學與光激發光性質,發現聚奎琳具有相當低能量的p-p*電子躍遷(lmax at 363-394 nm),放光顏色為藍光到黃綠光。由電化學研究,聚奎琳的HOMO介在-5.90 ~ -5.65 eV、LUMO介在-2.87 ~ -2.56 eV,此系列聚奎琳有較低的LUMO能階,顯示此類的聚奎琳有可能當高分子發光二極體元件的電子傳輸/電洞阻隔材料。
Polyquinolines containing spirobifluorene units in the main chain were synthesized via the Friedlander quinoline synthesis. In the spiro-fused bifluorene, the two mutually perpendicular fluorene rings were connected via a common tetracoordinated carbon atom. This structural feature leads to polymers possessing high thermal stability and good solubility in common organic solvents. The optical and photoluminescent properties of these polyquinolines were examined. The polyquinolines have similar lowest energy transition attributed to p-p* transition with lmax at 363-394 nm and exhibit blue to yellow-green emission. Cyclic voltammetry studies reveal that the range of HOMO of these polyquinolines were from –5.90 to –5.65 eV, and LUMO level were from –2.87 to –2.56 eV. The reversible reduction and low-lying LUMO energy level suggest that some of the polyquinolines may be potential materials for electron injection and transport in polymer LEDs.
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