新型二烷基芐基丙二酸二酯碳六十衍生物與其多加成衍生物之合成鑑定與性質分析

Synthesis and Characterization of Dialkylbenzyl 1,2-Methano[60]fullerene-61,61-Dicarboxylate Deterivatives and Their Multiple Adducts

王明道(Ming-Dao Wang)

指導教授 ： 芮祥鵬

國立臺北科技大學/工程學院/有機高分子研究所/碩士(2010年)

摘要

碳六十具有卓越的電子受體特性，近年來已被廣泛地應用在有機太陽能電池。然而碳六十分子本身對於一般低沸點有機溶劑的溶解度並不好，所以嚴重限制了它與共軛高分子(電子施體)的混掺效果。因此，藉由改質成相容性較佳的碳六十衍生物與共軛高分子混掺，有助於形成良好的異質界面型態，進而提升有機薄膜太陽能電池的光電轉換效率。在眾多碳六十衍生物的改質方式中，Bingel-Hirsch reaction具有高產率與合成途徑簡便之優點，為常用的碳六十衍生物改質方式之ㄧ。在本研究中，我們利用Bingel-Hirsch reaction成功合成了一系列溶解度較佳的dialkylbenzyl 1,2-methano[60]fullerene -61, 61-dicarboxylate 碳六十衍生物–dibenzyl 1,2-methano[60]fullerene-61,61-dicarboxylate（DBMDC）、bis(4-ethylbenzyl)1,2- methano[60] fullerene-61,61-dicarboxylate（BEBMDC）、bis(4-tert-butylbenzyl) 1,2-methano [60]fullerene-61,61-dicarboxylate（BtBBMDC）及其多加成取代衍生物–bis-dibenzyl 1,2-methano[60]fullerene-61,61- dicarboxylate (bis-DBMDC) 、bis-bis(4-tert-butylbenzyl) 1,2-methano [60]fullerene -61,61-dicarboxylate (bis-BtBBMDC)、tris-dibenzyl 1,2-methano[60]fullerene -61,61-dicarboxylate (tris-DBMDC)、tris-bis(4-tert-butylbenzyl) 1,2-methano [60]fullerene-61,61- dicarboxylate (tris-BtBBMDC)並對它們的光電性質加以研究。我們藉由1H NMR、13C NMR、MALDI-TOF MS、elemental analysis（EA）與UV-Vis吸收光譜鑑定這一系列碳六十衍生物的分子結構。並藉由UV-Vis吸收光譜與cyclic voltammetey（CV）獲得各別分子的band gap，HOMO與LUMO能階。

關鍵字

高分子太陽能電池 ； 富勒烯衍生物 ； Bingel-Hirsch reaction

並列摘要

Buckminsterfullerene (C60) has been widely used as excellent electron acceptor in organic solar cells. However, its minimal solubility in organic solvents necessitates derivatization to have good compatibility with donor-type conjugated polymers to achieve favorable morphology. Several pathways have been developed to functionalize C60 with solubilizing moieties. Among these methods, Bingel-Hirsch reaction is one of the most convenient routes to produce fullerene adduts. In Bingel-Hirsch reaction, C60 dicarboxylate can be prepared with very high yield in few synthetic steps. In this study, a series of novel soluble fullerene derivatives bearing different alkyl substitutions and their mutiple adducts, including dibenzyl 1,2-methano[60]fullerene-61,61-dicarboxylate (DBMDC), bis(4-ethylbenzyl) 1,2-methano[60] fullerene-61,61-dicarboxylate (BEBMDC), bis(4-tert-butylbenzyl) 1,2-methano[60]fullerene-61,61-dicarboxylate (BtBBMDC), bis-dibenzyl 1,2-methano[60]fullerene-61,61-dicarboxylate (bis-DBMDC), bis-bis (4-tert-butylbenzyl) 1,2-methano[60]fullerene-61,61- dicarboxylate (bis-BtBBMDC), tris-dibenzyl 1,2-methano[60]fullerene-61,61-dicarboxylate (tris-DBMDC), tris-bis(4-tert-butylbenzyl) 1,2-methano[60]fullerene-61,61-dicarboxylate (tris-BtBBMDC) were synthesized via Bingel-Hirsch reaction. The molecular structure of these novel fullerene derivatives was characterized by 1H NMR, 13C NMR, MALDI-TOF MS, elemental analysis (EA) and UV-Vis techniques. UV-Vis and cyclic voltammetey (CV) techniques were employed to determine their energy band gaps, highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels.

並列關鍵字

Bingel-Hirsch reaction ； Fullerene derivatives ； Polymer solar cells

參考文獻

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