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  • 學位論文

雙胺基五苯荑之合成與芳烴二醯亞胺之電子作用行為之研究

Synthesis of Pentiptycene Diamines and Their Electronic Interactions with Arene Diimides

指導教授 : 楊吉水

摘要


本論文主要目的在合成雙胺基五苯荑分子,ID及TMID。焦蜜石二醯亞胺(pyromellitic diimide, PDI-Bz)、萘四羧酸二醯亞胺 (naphthalene diimide, NDI-Bz)分別作為電子予體及電子受體。藉由混合兩者形成電荷轉移錯合物。儘管五苯荑骨架之側環具有較大的立體阻礙,我們依然發現兩者在混合的過程中可能有電荷轉移錯合物生成。更進一步,我們照光進行光誘導電荷轉移,我們發現ID分子混和PDI-Bz及NDI-Bz分子在乙腈溶劑中照光後,其顏色由透明轉為淡紅,且此紅色可以持續一段時間。 我們利用電化學分別針對TMID、ID、PDI-Bz、NDI-Bz進行電化學相關測試,藉以計算出施體及受體之HOMO與LUMO,藉以了解分子相對的能階。並進一步對ID分子及TMID分子進行光譜電化學實驗,用以判斷分子在進行光誘導電子轉移後,其中之物種是為自由基離子態或陰陽離子態。

關鍵字

五苯荑 二醯亞胺

並列摘要


In this thesis, we repot the synthesis of diamino pentiptycenes, ID and TMID, naphthalene diimide, NDI-Bz and pyromellitic diimide, PDI-Bz. The former two compounds are electron donors and the latter two are acceptors. When we mixed the donor and acceptors, charge transfer complexes might form even though the donors are bulky. Upon irradiation, we observed a color change from transparent to red, and the red solution could persist for a long time. We estimated the HOMO and LUMO of donors and acceptors by the redox potentials of donor and acceptor molecules, respectively. We also carried out spectroelectrochemistry to characterize the species formed after phototinduced electron transfer between the donors and acceptors.

並列關鍵字

Pentiptycene Diimides

參考文獻


1. Mataga, N.; Miyasaka, H. Electron Transfer and Exciplex Chemistry. In Adv. Chem. Phys., John Wiley & Sons, Inc.: 2007; pp 431-496.
2. Mulliken, R. S. Molecular Compounds and their Spectra. III. The Interaction of Electron Donors and Acceptors. J. Phys. Chem. 1952, 56, 801-822.
3. Benesi, H. A.; Hildebrand, J. H. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J. Am. Chem. Soc. 1949, 71, 2703-2707.
4. Akamatu, H.; Inokuchi, H. ; Matsunaga, Y. Electrical Conductivity of the Perylene-Bromine Complex. Nature 1954, 173, 168-169.
5. Ferraris, J.; Cowan, D. O.; Walatka, V.; Perlstein, J. H. Electron Transfer in a New Highly Conducting Donor-Acceptor Complex. J. Am. Chem. Soc. 1973, 95, 948-949.

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