合成含呋喃與菲之環芃烯

Hao-Tien Bai; 白皓天

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完整後設資料紀錄

DC 欄位	值	語言
dc.contributor.advisor	陸天堯(Tien-Yau Luh)
dc.contributor.author	Hao-Tien Bai	en
dc.contributor.author	白皓天	zh_TW
dc.date.accessioned	2021-06-15T00:42:40Z	-
dc.date.available	2010-09-17
dc.date.copyright	2008-09-17
dc.date.issued	2008
dc.date.submitted	2008-09-04
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dc.identifier.uri	http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/42026	-
dc.description.abstract	環芃這類化合物對於研究放光團透過空間作用是個好的模型。雜環環芃烯也是令人感興趣的系統，但文獻中含呋喃環芃烯是較少被關注的。而菲這個類平面芳香環，在環芃烯系統中其易聚集的性質，在光物理上已廣泛的被討論。　　過去我們已成功地利用呋喃成環反應，與McMurry反應合成到一系列的含呋喃之[n.2]環芃烯40a-f與環芃雙烯67。並經由EFISH，HRS的實驗確定這類化合物具有非線性光學性質。而為了深入了解這類系統，我們引入菲於環芃烯中，合成到環芃雙烯類似物69與70，兩者由EFISH實驗確定都有μβ值。也讓我們知道，將67中二苯代乙烯的架構，置換成菲結構的69或70，導致原雙鍵可當作acceptor的性質，在換成菲後變得不明顯。且由核磁共振光譜的動力學實驗與DFT理論計算，可知菲提供了69與70更加剛性的構型，導致另ㄧ端雙鍵部份，形成具有強環張力性質的雙鍵，是導致69有非線性光學性質的主因之一。但不同的是，在70中呋喃當donor而強拉電子基乙基酯當acceptor可形成電荷分離的結構，因而具有非線性光學性質。而正丁基呋喃環芃烯40a，67，69並不具有強推拉電子基，但構型上存在著具有環張力性質的雙鍵，可當acceptor與呋喃當donor的性質共同發揮，使其具有非線性光學特性。	zh_TW
dc.description.abstract	Cyclophanes have provided useful models for the investigation of through-space interactions between chromophores. Heterophanes also were interesting systems, but the discussing of furan-containing cyclophene was rare. It was well documented that phenanthrene-containing cyclophene, such a ring and planar aromatic structure was easy aggregated in photophysic. 　　Recently, we have detailed a new series of furan-containing teraryl cyclophene derivatives 40a-f and 67. And two keys to syntheses were one-pot furan annulation and the McMurry reaction. It is noteworthy that they exhibit unusually large Stokes shifts and NLO properties through EFISH or HRS experiment. In order to going deeper to these cyclophenes, we obtained furan, phenanthrene-containing cyclophenes 69 and 70 which exhibit NLO properties and μβ value. 　　It’s different property that a double bond as an electron acceptor, when cis-stilbene of 67 was replaced to phenanthrene of 69 or 70. And 69 contained the high rigid structure and a strong twisted double bond, which were proved by dynamic NMR experiment and DFT calculation. Such a twisted system may thus induce significant enhancement in hyperpolarizability. It’s interesting to note that 70, contained the strong electron withdrawing group (-CO2Et), was different property that charge transfer could only occur in the furan moiety with ester group from others. We expected a bridged double bond as an electron acceptor and furan as an electron donor for optical nonlinearity of cyclophenes may only take place in n-Bu substituted cases (40a, 67 and 69).	en
dc.description.provenance	Made available in DSpace on 2021-06-15T00:42:40Z (GMT). No. of bitstreams: 1 ntu-97-R94223007-1.pdf: 2230171 bytes, checksum: 6a419699d2d744976ce75ba48b874d57 (MD5) Previous issue date: 2008	en
dc.description.tableofcontents	口試委員會審定書謝誌 I 中文摘要 II 英文摘要 III 章節目錄 IV 表目錄 V 圖目錄 VI 附錄 VII 第一章緒論 1 1.1 前言 1 1.2 含菲之環芃烯 4 1.2a 菲的合成 4 1.2b 菲環的應用 4 1.2c 含菲之環芳或輪烯 6 1.3 官能基化炔丙基硫縮酮 8 1.3a 背景介紹 8 1.3b 合成炔丙基硫縮酮 14 1.4 合成含呋喃之環芃(雙)烯 17 1.5 合成動機 22 第二章合成含呋喃與菲之環芃烯 23 2.1合成正丁基取代含呋喃與菲之環芃烯69 23 2.1a 逆合成分析 23 2.1b 合成菲-3,6-雙醛73 24 2.1c 由化合物72、73建構環芃烯69 26 2.2合成乙基酯取代含呋喃與菲之環芃烯70 27 2.2a 逆合成分析 27 2.2b以83合成乙基酯炔丙基硫縮酮81 29 2.2c 以84合成乙基酯炔丙基硫縮酮81 31 2.2d 由化合物81、73建構環芃烯70 33 2.3合成含有炔丙基硫縮酮的三聯芳香環99 34 2.4合成呋喃之寡聚物 35 2.5 呋喃與菲之環芃烯核磁共振光譜探討 36 2.6含呋喃與菲之環芃烯光物理性質探討 41 2.7含呋喃與菲之環芃烯電化學與非線性光學性質探討 54 第三章總結與展望 63 第四章實驗部份 65 第五章參考文獻 96 表目錄表 2-1 在不同當量數NaH與MeI對93進行烷基化反應 32 表 2-2 化合物67, 69, 70 a-h位置1H核磁共振光譜 36 表 2-3 化合物69, 70, 79, 96, 103在氯仿中螢光衰減光譜之生命期 53 表 2-4 含呋喃寡聚物與環芃烯電化學性質整理 54 表 2-5 化合物40a, 67, 69, 70, 79, 96之光物理性質 58 圖目錄圖 1-2.1 含菲環疊合之非核苷雙股去氧核醣核酸圖 5 圖 1-4.1 化合物40吸收與放射光譜 18 圖 1-4.2 化合物40a，59之HOMO與LUMO結構分佈圖 19 圖 1-4.3 化合物40非線性光學之muBeta值與分子夾角關係圖 20 圖 1-4.4 化合物67，68吸收與放射光譜圖 21 圖 2-5.1 化合物69 1H NMR 圖 2-5.2 化合物70 1H NMR 18 圖 2-5.3 化合物40a在二氯甲烷中所測變溫1H NMR 72 圖 2-5.4 化合物69在二氯甲烷中所測變溫1H NMR 2 圖 2-5.5 化合物70在二氯甲烷中所測變溫1H NMR 18 圖 2-6.1 化合物79與96在氯仿中吸收與螢光歸一化光譜 41 圖 2-6.2 化合物79在氯仿中不同激發波長下螢光歸一化光譜 42 圖 2-6.3 化合物79在氯仿中吸收，激發與螢光歸一化光譜 42 圖 2-6.4 化合物96在氯仿中不同激發波長下螢光光歸一化光譜 43 圖 2-6.5 化合物96在氯仿中吸收，激發與螢光歸一化光譜 43 圖 2-6.6 化合物70與96在氯仿中吸收與螢光歸一化光譜 44 圖 2-6.7 化合物70在氯仿中不同激發波長下螢光歸一化光譜 44 圖 2-6.8 化合物70在氯仿中吸收，激發與螢光歸一化光譜 45 圖 2-6.9 化合物70在氯仿中不同濃度下螢光未歸一化光譜 45 圖 2-6.10 化合物69與79在氯仿中吸收與螢光歸一化光譜 47 圖 2-6.11 化合物69與70在氯仿中吸收與螢光歸一化光譜　 47 圖 2-6.12 化合物67與69可能的電荷分離結構 48 圖 2-6.13 化合物67與69在氯仿中吸收與螢光歸一化光譜 48 圖 2-6.14 化合物40a與69在氯仿中吸收與螢光歸一化光譜 49 圖 2-6.15 化合物69在氯仿中不同濃度下螢光未歸一化光譜 49 圖 2-6.16 化合物69在氯仿中不同激發波長下螢光歸一化光譜 50 圖 2-6.17 化合物69在氯仿中吸收，激發與螢光歸一化光譜 50 圖 2-6.18 化合物69、70在氯仿中時間解析螢光衰減光譜 52 圖 2-6.19 化合物79、96在氯仿時間解析中螢光衰減光譜 52 圖 2-6.20 化合物103在氯仿中時間解析螢光衰減光譜 53 圖 2-7.1 化合物69，70之HOMO與LUMO結構分佈圖 60 圖 2-7.2 化合物40a，67，69，70可能電荷結構分佈圖 60 圖 2-7.3 化合物79，96可能電荷結構分佈圖 61 圖 2-7.4 化合物69溶媒色移法線性迴歸圖 62 附錄附錄Ａ非線性光學儀器與化合物測量值與不同溶劑下69歸一化吸收光譜圖 105 附錄B　化合物循環伏安圖與差別脈衝伏安圖 109 附錄C　化合物之1H NMR光譜 113
dc.language.iso	zh-TW
dc.title	合成含呋喃與菲之環芃烯	zh_TW
dc.title	Synthesis Furan, Phenanthrene-Containing Cyclophenes	en
dc.type	Thesis
dc.date.schoolyear	96-2
dc.description.degree	碩士
dc.contributor.oralexamcommittee	陳錦地(Chin-Ti Chen)
dc.subject.keyword	呋,喃,菲,環芃烯,非線性光學,	zh_TW
dc.subject.keyword	Furan,Phenanthrene,Cyclophenes,NLO,	en
dc.relation.page	133
dc.rights.note	有償授權
dc.date.accepted	2008-09-04
dc.contributor.author-college	理學院	zh_TW
dc.contributor.author-dept	化學研究所	zh_TW
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