芳香族雙醚烯類化合物的臭氧化反應與其化學發光之機制研究

Study on the Mechanism of Chemiluminescent Ozonization of Aromatic Dialkoxy Alkenes

簡森乙(Senyi Chren)

指導教授 ： 方泰山

國立臺灣師範大學/理學院/化學系/碩士(2000年)

摘要

本實驗室長久致力於芳香族雙醚烯化合物(dioxene)相關反應，其中著墨於臭氧化反應和單態氧化反應尤甚，並研究其臭氧化化學發光。本論文乃再探究並統整本研究室三大標題化合物A,B,C，針對其臭氧化化學發光反應其伴隨的的反應性質，推究其反應機構並探討其化學發光性質。
化合物A、B、C由AAQ(anthracenequinone)；ANQ(acenaphthenequinone)；以及PNQ(phenanthrenequinone)分別與2,3-二甲基-2-丁烯進行光加成反應而得。
將化合物A,B,C分別溶於二氯甲烷中，並在-78℃下進行臭氧化反應，當溫度慢慢回復至室溫，可以發現化合物A、B均有化學發光的現象，而化合物C則無此現象，致光物質經實驗證實為1,2-雙氧烷〈1,2-dioxetane〉，而主產物為經臭氧化重排的穩定過氧化物。
本論文亦將三種標題化合物進行臭氧化反應後的反應機構亦作深入的探討與比較。
化合物A 化合物B 化合物C
(紫黑色) (紅色) (無色)

關鍵字

蔥并二酮 ； 1,2-雙氧烷厄烯奈 ； 10,10,11,11-四甲基并菲基[9,10-b]-[1,4]-雙氧醚

並列摘要

Oxidizing chemiluminescence of aromatic dioxenes has been studying in Professor Fang’s Laboratory ,especially focussed on ozonization and singlet oxygen reaction .
The thesis is mainly to revisit and summarize the chemiluminescence properties and their reaction of compound A , B and C , respectively , with ozone in dicholoromethane .
The compounds A , B and C were obtained by photochemical reaction of AAQ(anthracenequinone) ; ANQ(acenaphthenequinone) and PNQ(phenanthrenequinone) , respectively , with 2,3-dimethyl-2-butene(TME) in benzene .
Compounds A , B and C were respectively dissolved in dicholoromethane and ozonized at low temperature(-78℃) . When warms up the solution to room temperature , one can obviously see both ozonides A and ozonides B emit beautiful light , but ozonides C doesn’t . Evidence show that the identify of chemiluminescence is the dioxetane . The major product in this process is the rearranged ozonized adduct .
The mechanism of chemiluminescence as well as the ozonizaton is to be discussed .
compound A compound B compound C
(double violet) (red) (colorless)

並列關鍵字

AAQ(anthracenequinone) ； ANQ(acenaphthenequinone) ； PNQ(phenanthrenequinone)

參考文獻

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