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???org.dspace.app.webui.jsptag.ItemTag.dcfield??? | Value | Language |
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dc.contributor.advisor | 周必泰(Pi-Tai Chou) | |
dc.contributor.author | Jiun-Yi Shen | en |
dc.contributor.author | 沈俊義 | zh_TW |
dc.date.accessioned | 2021-06-13T06:59:40Z | - |
dc.date.available | 2013-07-29 | |
dc.date.copyright | 2011-07-29 | |
dc.date.issued | 2011 | |
dc.date.submitted | 2011-07-22 | |
dc.identifier.citation | Chapter 1
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/35584 | - |
dc.description.abstract | 第一部分
我們成功的合成一系列含氰基的7-氮雜吲哚(7AI)如:3-氰基-7-氮雜吲哚(3CNAI),5-氰基-7 -氮雜吲哚(5CNAI),3,5-二氰基-7-氮雜吲哚(3,5CNAI)和2-亞甲基丙二腈-7-氮雜吲哚(DiCNAI)。研究此7-氮雜吲哚衍生物在不同質子性溶劑裡激發態質子轉移和電荷轉移反應之間的相互作用,7AI、3CNAI和3,5CNAI在甲醇催化下進行激發態雙質子轉移(ESDPT),造成兩種物質(質子轉移前的正常體和質子轉移後的互變異構體)的放光。相反地,5CNAI和DiCNAI在甲醇催化下不會進行激發態雙質子轉移,只有產生高量子效率的質子轉移前的正常體放光,並且這些正常體的放光具有溶劑化顯色現象。進行鬆弛動力學和溫度相關的詳細研究。結果得出結論,5CNAI和DiCNAI進行激發態電荷轉移(ESCT)。電荷轉移化合物相對於質子轉移異構體化合物擁有不同的偶極矩。在到達極化平衡,存在溶劑的極性引起質子轉移互變異構的能障造成5CNAI和DiCNAI不進行 ESDPT。其結果是明顯不同於一般的7AI,這也是至今其中最獨特的激發態電荷/質子轉移耦合系統的研究。 第二部分 我們成功的合成一系列含有2,7-咔唑基團有機染料(SJY1- SJY5)及用於染料敏化太陽能電池。量測其吸收光譜,電化學和光電性能。電化學測量數據顯示不同的推電子基團可以調控化合物的HOMO和LUMO能階。在液體電解質染料敏化太陽能電池(DSSCs)中,按照標準的全球AM 1.5太陽光照條件SJY2 化合物具有最佳的光電轉換效率6.02% 其短路電流密度(JSC)14.45毫安培/平方公分,開路電壓(VOC)為 0.65 伏特和填充因子(FF)為 0.65。然而,SJY4化合物在液體電解質染料敏化太陽能電池中效果的最差,其整體轉換效率為3.36%,但應用於固態太陽能電池中卻有提高光電轉換效率到達3.90%(VOC = 0.91 伏特,JSC = 6.86毫安培/平方公分和FF=0.62)。引入兩個星形三芳香胺基可能是一種方法,作為推電子天線群可以增加摩爾消光係數而提升短路電流密度值,還有防止分子之間的堆疊並可以使光敏化染料快速的再生。 | zh_TW |
dc.description.abstract | Part I
We have synthesized a series of 7-azaindole (7AI) bearing cyano groups. The interplay between excited-state charge and proton transfer reactions in protic solvents is investigated in a series of 7-azaindole derivatives: 3-cyano-7-azaindole (3CNAI), 5-cyano-7-azaindole (5CNAI), 3,5-dicyano-7-azaindole (3,5CNAI) and dicyanoethenyl-7-azaindole (DiCNAI). Similar to 7AI, 3CNAI and 3,5CNAI undergo methanol catalyzed excited-state double proton transfer (ESDPT), resulting in dual (normal and proton transfer) emission. Conversely, ESDPT is prohibited for 5CNAI and DiCNAI in methanol, as supported by a unique normal emission with high quantum efficiency. Instead, the normal emission undergoes prominent solvatochromism. Detailed relaxation dynamics and temperature dependent studies are carried out. The results conclude that significant excited-state charge transfer (ESCT) takes place for both 5CNAI and DiCNAI. The charge-transfer specie possesses a different dipole moment from that of the proton-transfer tautomer species. Upon reaching the equilibrium polarization, there exists a solvent-polarity induced barrier during the proton-transfer tautomerization, and ESDPT is prohibited for 5CNAI and DiCNAI during the excited-state lifespan. The result is remarkably different from 7AI, which is also unique among most excited-state charge/proton transfer coupled systems studied to date. Part II Five new metal-free organic dyes (SJY1–SJY5) containing 2,7-carbazole moieties were synthesized and used for dye-sensitized solar cells (DSSCs). Their absorption spectra, electrochemical and photovoltaic properties were fully characterized. Electrochemical measurement data indicate that the tuning of the HOMO and LUMO energy levels can be conveniently accomplished by alternating the donor moiety. The liquid electrolyte DSSCs based on the SJY2-sensitized exhibited the | en |
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dc.description.tableofcontents | Contents
口試委員會審定書…………………………………………………………………………………I 摘要………………………………….....................................……………………………………II Abstract…………………………………………………………………............................……….IV Figure captions................................................................................................................................VIII Scheme Captions................................................................................................................................XI Table Captions..................................................................................................................................XII Chapter 1. Diaza-18-Crown-6 Appended Dual 7-Hydroxyquinolines; Mercury Ion Recognition in Aqueous Solution…………………………………………………………………………………….1 1.1 Introduction…………………………………………………………………………………1 1.2 Results and Discussion……………………………………………………………………...1 1.3 Conclusion…………………………………………………………………..……………..10 1.4 Supplementary Information……………………………………………….……………….10 1.5 Notes and references………………………………………………….……………………21 Chapter 2. Cyano Analogues of 7-Azaindole: Probing Excited-State Charge-Coupled Proton Transfer Reactions in Protic Solvents…………………………………………………....…………24 2.1 Introduction…………………………………………………………..……………………25 2.2 Results and Discussion…………………………………………….……………………31 2.3 Conclusions………………………………………………………………………………45 2.4 Experimental Section…………………………………………………..………………..47 2.5 References……………………………………………………………………………….52 Chapter 3. Metal-Free Organic Dyes Containing the 2,7-Carbazole Moiety for Dye-Sensitized Solar Cells…………………………………………………...…………………………………………….58 3.1 Introduction………………………………………………………………………………..58 3.2 Experimental Section……………………………………………………………..………61 3.3 Results and Discussion…………………………………………………………………….76 3.3.1 Synthesis and optical properties………………………………………..…………..76 3.3.2 Electrochemical properties……………………………………………………….80 3.3.3 Photovoltaic performance of liquid electrolyte DSSCs……………………….81 3.3.4 Photovoltaic performance of solid-state DSSCs………………..………………….85 3.4 Conclusion…………………………………………………………………...…………….86 3.5 References……………………………………………………………………………….87 Figure Captions Fig. 1.1. Absorption spectra of TDBQ (7.8 μM) in H2O (a, pH = 7) upon addition of Hg2+ in an increment of 6.7 μM (b–k), followed by 13.3 μM (l–z), 33.4 μM (ai–am). Inset: Absorbance at 358 nm against [Hg2+]…………………………………………………………………………………….4 Fig. 1.2. (A) The increase of absorption at 358 nm was plotted against the mole fraction of Hg2+ (Job’s plot). [TDBQ] + [Hg2+] = 7.0 μM. (B) The plot of C0/(Aab − εTDBQC0) against 1/Cg2 at 358 nm (see text)………………………………………………………………………..…………………….5 Fig. 1.3. Emission spectra of TDBQ (7.8 μM in H2O, pH = 7) upon addition of Hg2+ in an increment of 133.3 μM (a–b), followed by 33.3 μM (c–i), λex = 358 nm; (j) (-○-) The addition of 1 mM DMPS on (i). (k) (-△-) The addition of 1.5 mM [Hg2+] on (j). λex = 358 nm…………………………………………………………………………………………………..9 Figure 1.S1. 1H NMR spectra of TDBQ in CDCl3………………………………………………..12 Figure 1.S2. The extension of 1H NMR spectra of TDBQ in CDCl3…………………………….12 Figure 1.S3. 13C NMR of TDBQ in CDCl3. (125MHz)………………………….………………13 Figure 1.S4. HRMS of TDBQ………………………………………...………………………….13 Figure 1.S5. ORTEP diagram of (a) TDBQ and (b) TDBQ-mercury crystal with thermal ellipsoids shown at 30% probability level……………………………………………………………………17 Figure 1.S6. Normalized XANES spectra for TDBQ-mercury crystal (-•-), HgCl2 (Gray), and Hg2Cl2 (black)………………………………………………………………………………………20 Figure 1.S7. Absorbance (364 nm) of TDBQ (1.5 μM) in aqueous solution at various pH values : | |
dc.language.iso | en | |
dc.title | 第一部分: 激發態質子轉移化合物之合成與研究
第二部分: 含2,7-咔唑有機染料敏化太陽能電池之研究 | zh_TW |
dc.title | Part I: Synthesis and Study of Excited-State Proton-Transfer Compounds
Part II: Organic Dyes Containing the 2,7-Carbazole Moiety for DSSCs | en |
dc.type | Thesis | |
dc.date.schoolyear | 99-2 | |
dc.description.degree | 博士 | |
dc.contributor.oralexamcommittee | 趙登志,陳奎佑,康佳正,何美霖 | |
dc.subject.keyword | ESDPT,7-氮雜吲,哚,激發態,電荷轉移,質子轉移,DSSCs,2,7-咔,唑,堆疊,三芳香胺基,再生, | zh_TW |
dc.subject.keyword | ESDPT,7-azaindole,excited-state,charge transfer,proton transfer,DSSCs,2,7-carbazole,aggregation,triarylamines,regeneration, | en |
dc.relation.page | 93 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2011-07-22 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
Appears in Collections: | 化學系 |
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