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研究生: 蔡宗祐
Tsai, Tsung-Yu
論文名稱: 主鏈剛性及結構規整性對於共軛高分子分選半導型單壁奈米碳管之影響及場效電晶體應用
Effects of Backbone Rigidity and Structural Regularity of Conjugated Polymers on semiconducting Single-Walled Carbon Nanotube Sorting and Field-Effect Transistor Applications
指導教授: 林彥丞
Lin, Yan-Cheng
學位類別: 碩士
Master
系所名稱: 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年: 2026
畢業學年度: 114
語文別: 英文
論文頁數: 127
中文關鍵詞: 共軛高分子序列規律性單壁奈米碳管奈米材料有機電子元件
外文關鍵詞: conjugated polymers, sequential regularity, single-walled carbon nanotube, nanomaterials, organic electronics
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  • 共軛高分子纏繞法為目前最具前景的半導體型單壁奈米碳管分選策略,然而高分子骨架剛性與結構規律性對分選行為的影響尚未獲得系統性探討。本研究設計並合成一系列以萘二醯亞胺為受體、噻吩衍生物為給體的供受體型共軛高分子,包含單噻吩(T1)、雙噻吩(T2)、三聯噻吩(T3)及隨機共聚物(T1-3),系統探討骨架共軛長度與結構規律性對半導體型單壁奈米碳管分選效率及場效電晶體元件性能的影響。利用高分子包覆策略進行半導體型單壁奈米碳管分選時,高分子的骨架構型同時決定其在溶液中的聚集行為與對碳管表面的包覆能力,兩者之間的競爭關係是影響分選效率的關鍵因素,但系統性探討尚不充分。光學與電化學分析顯示,隨噻吩供體單元數增加,主吸收峰持續紅移,光學能隙縮小,最高佔據分子軌域能階上升;最低未佔據分子軌域能階則受萘二醯亞胺受體主導。聚集分率分析顯示,T2 與 T3 因骨架共平面性較高而呈現明顯聚集;T1因供體共軛長度不足,聚集傾向極低;T1-3 則透過隨機序列排列破壞鏈間 π–π 堆疊幾何,使聚集程度大幅低於 T3 均聚物。密度泛函理論計算確認,T2 骨架最為共平面,T3 次之,T1-3 中三聯噻吩片段的二面角因序列不規律被大幅扭轉,從分子層面解釋了低聚集分率的成因。分選效率方面,四個高分子半導型奈米碳管純度均 ≥ 99%,分選產率隨噻吩單元數增加而提升,T1-3的產率更顯著超越線性預測,源於低聚集分率維持較高自由鏈濃度,以及 T1 片段提供的包覆構型自由度兩者的協同效應。原子力顯微鏡量測顯示薄膜表面粗糙度與溶液中的聚集程度高度對應,聚集分率較高者薄膜亦較粗糙。奈米碳管電晶體量測顯示,T1-3在電洞遷移率方面表現最佳,T2 因薄膜粗糙度偏高、有效通道接觸面積受限而遷移率最低;電流開關比則以半導型奈米碳管純度較高的 T1 與T3 表現突出。本研究確立兩項設計原則:(一)骨架共軛長度決定分選產率與手性偏好;(二)透過隨機共聚合調控結構規律性,可在不依賴特殊側鏈或摻混策略的情況下,同時提升產率、降低薄膜粗糙度並改善元件遷移率,為共軛高分子骨架工程作為半導型奈米碳管分選設計策略提供新的實驗依據。

    Conjugated polymer wrapping is currently the most promising strategy for sorting semiconducting single-walled carbon nanotubes (s-SWCNTs); however, the effects of polymer backbone rigidity and structural regularity on sorting behavior have not yet been systematically investigated. This study designs and synthesizes a series of donor-acceptor conjugated polymers based on naphthalene diimide (NDI) as the acceptor and thiophene derivatives as the donor, including thiophene (T1), bithiophene (T2), terthiophene (T3), and a random copolymer (T1-3). The series systematically investigates the effects of backbone conjugation length and sequential regularity on the sorting efficiency of semiconducting single-walled carbon nanotubes and on carbon nanotube field-effect transistor (CNT-FET) device performance. In polymer-wrapping-based s-SWCNT sorting, the backbone conformation of the polymer governs both its aggregation behavior in solution and its wrapping capability on the nanotube surface. The competition between these two factors is a key determinant of sorting efficiency, yet systematic investigation remains limited. Optical and electrochemical characterization shows that increasing the number of thiophene donor units produces a progressive red shift in the main absorption peak, a narrower optical bandgap, and a higher HOMO level, while the LUMO level remains largely unchanged under the influence of the NDI acceptor. Aggregation fraction analysis reveals that T2 and T3 exhibit pronounced aggregation due to their high backbone coplanarity, whereas T1 shows minimal aggregation owing to insufficient donor conjugation length. T1-3 disrupts interchain π–π stacking geometry through its random monomer sequence, reducing aggregation to well below that of the T3 homopolymer. Density functional theory calculations confirm that the T2 backbone is the most coplanar, followed by T3; the terthiophene segments in T1-3 are, in fact, similarly coplanar, but the irregular alternation of T1 and T3 units disrupts long-range backbone registry between chains, providing a molecular-level explanation for the reduced aggregation fraction. In terms of sorting efficiency, all four polymers achieve s-SWCNT purity ≥ 99%. Sorting yield increases with the number of thiophene units, and the yield of T1-3 substantially exceeds the linear prediction. This enhancement arises from the synergistic effect of a higher free-chain concentration maintained by the low aggregation fraction and the greater wrapping conformational freedom provided by the T1 segments. Atomic force microscopy measurements show that thin-film surface roughness correlates closely with solution-phase aggregation: polymers with a higher aggregation fraction produce rougher films. CNT-FET measurements show that T1-3 achieves the highest hole mobility, while T2 shows the lowest mobility due to high film roughness limiting the effective channel contact area. T1 and T3, which exhibit higher s-SWCNT sorting purity, show superior switching ratios. This study establishes two design principles. First, backbone conjugation length determines sorting yield and chiral preference. Second, tuning sequential regularity through random copolymerization can increase sorting yield, reduce thin-film roughness, and improve device mobility without relying on specialized side chains or polymer blending strategies. These findings provide experimental support for conjugated polymer backbone engineering as a design strategy for s-SWCNT sorting.

    摘要 i Abstract ii 誌謝 iv Contents v List of Figures viii List of Abbreviations xiii List of Tables xiv Chapter 1 Introduction 15 1.1 Preface 15 1.2 Conjugated Polymers 17 1.2.1 Characteristics of Conjugated Polymers 17 1.2.2 Side Chains 18 1.2.3 Main Chain 19 1.2.4 Donor-Acceptor Strategy 20 1.3 Single-Walled Carbon Nanotubes 21 1.3.1 Synthesis and Manufacture 22 1.3.2 Structure and Chirality 25 1.3.3 s-SWCNTs and m-SWCNTs 27 1.3.4 SWCNT Sorting 28 1.4 Field-Effect Transistors 32 1.4.1 Fundamentals of FETs 33 1.4.2 Organic Field-Effect Transistors (OFETs) 34 1.4.3 CNT-FETs 34 1.4.4 Parameters and Equations 37 1.5 Research Objectives 38 Chapter 2 Experimental Methods 40 2.1 Research Methods 40 2.2 Reagents and Chemicals 42 2.2.1 Reagents 42 2.2.2 Synthesis 43 2.3 Instruments and Characterization Methods 53 2.3.1 Polymer Characterization 53 2.3.2 Computational Methods 54 2.3.3 Morphological characterization 55 2.3.4 Optical and Electrochemical Characterization 55 2.3.5 Device Fabrication and Measurement 59 2.4 Device Fabrication Method 65 2.4.1 SWCNT Sorting Method 65 2.4.2 CNT-FET Sample Preparation 66 Chapter 3 Results and Discussion 70 3.1 Polymer Characterization 70 3.1.1 Chemical Structural Characterization 70 3.1.2 Molecular Weight Characterization 72 3.2 Absorption Spectroscopy 74 3.2.1 UV–Vis–NIR Spectroscopy 74 3.2.2 Aggregation Behavior 77 3.3 Electrochemical Characterization 81 3.4 Sorting Selectivity and Efficiency 84 3.4.1 Purity of s-SWCNT 85 3.4.2 Yield of s-SWCNT 87 3.5 s-SWCNT Characteristics 90 3.5.1 Raman Spectroscopy 90 3.5.2 PLE Analysis 94 3.6 Theoretical Calculations 98 3.6.1 DFT Simulations of Backbone Structure 98 3.6.2 MD Simulations of Carbon Nanotube Wrapping 101 3.7 Film Morphology 104 3.8 Transfer Characteristics 106 3.9 Comparison with Literature 111 Chapter 4 Conclusion and Future Work 115 4.1 Conclusion 115 4.2 Future Work 117 References 119

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