Synthesis of Oxindole Based Organic Sensitizers: Application in Dye-Sensitized Solar Cells

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丁永旭(Tingare Yogesh S.) 查詢紙本館藏

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化學學系

論文名稱

Synthesis of Oxindole Based Organic Sensitizers: Application in Dye-Sensitized Solar Cells

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摘要(中)

The present work deals with the design and synthesis of new organic sensitizers for the development of dye sensitized solar cells (DSSC). The oxindoles are natural indole alkaloids and are ubiquitous within the pharmaceutical industry. The following parts of this thesis regard with unprecedented incorporation of oxindoles as the novel building block for the development of new organic sensitizers. As a part of on-going research, alternating the molecular engineering and developing new strategies for utilization of such oxindole dyes to achieve higher light conversion efficiency was demonstrated. These strategies have so far been successful in terms of reaching respectful efficiencies for oxindole dyes in the DSSCs. Under the illumination of AM1.5 stimulated light, the highest photon-to-current conversion efficiency obtained for an oxindole dye (TI114) sensitized DSSC was 6.35%.

摘要(英)

本文設計並合成新穎的吲哚酮有機光敏染料，並將其應用於染料敏化太陽能電池。
吲哚酮是天然的吲哚啉類生物鹼，普遍使用在醫藥界。本篇論文以吲哚酮作為主體結構，設計出新穎之有機染料，是目前尚未發展的新方向。在持續的研究下，證明吲哚酮染料之新的合成策略及結構上的修飾可達高光電轉換效率。到目前為止，此類吲哚酮染料應用於染料敏化太陽能電池上有不錯的表現。
其中吲哚酮染料 TI114 在AM 1.5標準照光強度下測試，可達6.35%之光電轉換效率。

關鍵字(中)

關鍵字(英)

★ Oxindoles
★ halogens
★ Dye-sensitized solar cells

論文目次

Abstract…………………………………………………………………………………….i
Chinese Abstract……………………………………………………………………….ii
Chapter I
I-1: Introduction to Solar Cells 1
I-2: Components of the Dye-Sensitized Solar Cells 3
I-2.1 Nanocrystalline Semiconductor Oxide Film Electrode 3
I-2.2 Sensitizers 4
I-2.3 Electrolytes 5
I-2.3.1 Liquid electrolytes 6
I-2.3.2 Solid electrolytes 6
I-2.3.3 Quasi-solid electrolyte 8
I-2.4 Counter Electrodes 8
I-2.5 Transparent Conducting Substrate 8
I-3 Assembling of Dye-sensitized Solar Cell 9
I-4: Mechanism 9
I-4.1 Operating Principles 9
I-4.2 Side Reactions 11
I-5: Efficiency of Solar Cell 11
I-6: Chromophores 12
I-6.1 Ruthenium Based Chromophores 13
I-6.2 Metal-free Organic Chromophores 16
Chapter II
II-1: Research Motivation 21
II-2: Aim of the Study and Synthetic Strategy 22
II-3: Dye-Sensitized Solar Cells Based on Novel Oxindole Sensitizers: Enhancement in Performance through Halogen Substitutions 23
II-3.1 Introduction 23
II-3.2 Synthesis of Sensitizers TI111-TI116 26
II-3.3 Molecular geometries of ester 2b. 28
II-3.4 Molecular geometries of ester 8 29
II-3.5 UV/Vis absorption spectroscopy of TI111-TI116 dyes in solution and on film.. 30
II-3.6 Electrochemical Measurements 32
II-3.7 Performances of Dye-Sensitized Solar Cells 36
II-3.8 Conclusion 39
Chapter III
Oxindole Based Sensitizers: Synthesis and Application in Dye-Sensitized Solar Cells
III-1.1 Synthesis of Sensitizers TI124 and TI125 41
III-1.2 UV/Vis absorption spectroscopy of TI124 and TI125 dyes in solution and on film. 42
III-1.3 Electrochemical Measurements 44
III-1.4 Performances of Dye-Sensitized Solar Cells 46
III-1.5 Conclusion 48
Chapter IV
IV: Experimental Section 49
IV-1 Physicochemical Methods 49
IV-2 Preparation of TiO2 Electrodes and DSSC Device 50
IV-3 DSSC Performance Measurements 52
IV-4 Synthetic Procedures 52
IV-4.1 Synthesis of sensitizers TI111-TI116 52
IV-4.2 Synthesis of Sensitizer TI124 and TI125 59
IV.5 1H, 13C NMR and Mass spectra. 62
V: Reference 106

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指導教授

李文仁

審核日期

2013-8-29

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