乙基烷基苯基二酸二酯碳六十衍生物及其衍生雙取代化合物的合成與性質分析

Synthesis and Characterization of Ethyl Alkylbenzyl 1,2-Methano[60]fullerene-61,61-Dicarboxylate Derivatives and Their Bis Adducts

周子偉(Zi-Wei Chou)

指導教授 ： 芮祥鵬 ； 王立義

國立臺北科技大學/工程學院/有機高分子研究所/碩士(2011年)

摘要

碳六十具有良好的電子接收能力，因此它的衍生物已被廣泛地使用為製備高效率高分子太陽能電池中的受體材料。而且，它的分子能階及化學結構關鍵地影響著電池元件的效能。在本研究中，我們利用簡易的 Bingel-Hirsch reaction 、Prato reaction合成了一系列新穎的碳六十衍生物，包含：ethyl (4-methylbenzyl)1,2-methano[60] fullerene-61,61- dicarboxylate (MBEMDC)、ethyl (4-ethylbenzyl)1,2-methano[60]fullerene-61,61- dicarboxylate (EBEMDC)、ethyl (4-isopropylbenzyl) 1,2-methano[60]fullerene-61,61- dicarboxylate (iPBEMDC)、ethyl (4-tert-butylbenzyl) 1,2-methano[60] fullerene-61,61- dicarboxylate (tBBEMDC)、(4-n-butylbenzyl) 1,2-methano[60] fullerene-61,61- dicarboxylate (nBBEMDC) 、bis- ethyl (4-ethylbenzyl)1,2-methano[60]fullerene-61,61- dicarboxylate (bis-EBEMDC)、bis-ethyl (4-isopropylbenzyl) 1,2-methano[60]fullerene-61,61- dicarboxylate (bis-iPBEMDC)、bis-ethyl (4-tert-butylbenzyl) 1,2-methano[60] fullerene-61,61- dicarboxylate (bis-tBBEMDC)、benzyl-n-hexyl 1,2-methano[60]fullerene-61,61-dicarboxylate benzyl fulleropyrrolidine
(BHMDCmix) 、ethyl (4-tert-butylbenzyl) 1,2-methano[60] fullerene-61,61- dicarboxylate benzyl fulleropyrrolidine (tBBEMDCmix)。我們除了使用NMR、MALDI-TOF、EA來鑑定它們的化學結構之外，亦應用cyclic voltammetry (CV)來了解其電化學性質，UV-Vis來觀察它們的吸光特性，做為元件以後光電轉換效率之影響。藉此，我們將可進一步的碳六十衍生物之能階及溶解度與元件光伏特性之相關性。

關鍵字

高分子太陽能電池 ； 碳六十衍生物 ； Bingel-Hirsch reaction ； Prato reaction

並列摘要

Fullerene derivatives have been widely used as electron acceptor for fabricating efficient polymer solar cells due to their high electron affinity and good electron mobility. It has been demonstrated that the molecular levels, chemical compatibility to conjugated polymer and solubility in processing solvent are key parameters in affecting the cell efficiency. In this study, a series of mono- and bis-adducts of C60 with similar structure, including ethyl (4-methylbenzyl)1,2-methano[60]fullerene- 61,61-dicarboxylate (MBEMDC), ethyl (4-ethylbenzyl)1,2-methano[60]fullerene- 61,61-dicarboxylate(EBEMDC), ethyl (4-isopropylbenzyl) 1,2-methano[60]fullerene- 61,61-dicarboxylate (iPBEMDC), ethyl (4-tert-butylbenzyl) 1,2-methano[60] fullerene-61,61-dicarboxylate (tBBEMDC), (4-n-butylbenzyl) 1,2-methano[60] fullerene-61,61-dicarboxylate(nBBEMDC), bis-ethyl (4-ethylbenzyl)1,2-methano[60] fullerene-61,61-dicarboxylate (bis-EBEMDC), bis-ethyl (4-isopropylbenzyl)
1,2-methano[60]fullerene-61,61-dicarboxylate (bis-iPBEMDC), bis-ethyl (4-tert- butyl-benzyl)1,2-methano[60] fullerene-61,61-dicarboxylate(bis-tBBEMDC), benzyl- n-hexyl 1,2-methano[60]fullerene-61,61-dicarboxylate benzyl fulleropyrrolidine (BHMDCmix) and ethyl (4-tert-butylbenzyl) 1,2-methano[60]fullerene-61,61- dicarboxylate benzyl fulleropyrrolidine (tBBEMDCmix), were designed and synthesized via Bingel-Hirsch reaction and/or Prato reaction. The obtained products were characterized using NMR, MALDI-TOF and EA. Moreover, cyclic voltammetry (CV) and UV-vis were employed to investigate the energy levels and optical properties of these new molecules.

並列關鍵字

Polymer solar cells ； Fullerene derivatives ； Bingel-Hirsch reaction ； Prato reaction

參考文獻

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