三環疊苯衍生物的製備與研究

Abstract

我們主要是依循Teruo Shinmyozu教授的合成方法，順利合成出主體[3.3.3](1,3,5)Cyclophane-2,11,20-trione的結構，並且選擇catechol、naphthalene-2,3-diol，與自行合成的anthrance-2,3-diol，triphenylene-2,3-diol作為電子予體，利用Dean-Stark裝置進行脫水反應，而能成功的連接於主體上，形成一系列D-S-A系列的疊苯分子。除此之外，亦利用實際測量與理論計算研究此系列分子中，光譜消光的過程與能量及電子轉移之間的相關性。

Starting from [3.3.3](1,3,5) Cyclophane-2, 11, 20-trione, we were able to synthesize a series of donor-space-acceptor substituted derivatives (15-24) by condensation reaction. The component for the condensation was catechol, 2,3-naphthalenediol, 2,3-anthrancediol (14), and 2,3-triphenylenediol (10) for the donor part and the original carbonyl group was considered as acceptor part. We also synthesized the reference compounds [3.3.3](1,3,5) Cyclophane by using the Wolff-Kishner reduction. Fluorescence spectra provided evidence for efficient energy loss in the benzene, naphthalene, and triphenylene derivatives, but not in the analogous anthrance derivatives. The difference of energy transfer and electron transfer is very tricky. After our theoretical calculation and fluorescence discussion, we found that the energy loss should be follow by energy transfer instead of electron transfer.