本論文展示了一種新型二元非貴金屬（Co和Fe）的合成於金屬咕咯大環絡合物（FCC）中，通過單晶X射線衍射分析及其熱解形式其較低的對稱性質用於燃料電池應用內之氧還原反應。

本研究成功地利用多步合成了此FCC結構，並將二茂鐵基團鍵結鈷咕咯環中，並且與咕咯環的較少的相互作用。此外本研究亦克服FCC的麻煩的純化和產率改進的方法。並通過1H，13C NMR和FT-IR光譜證實了複合FCC結構。通過使用UV-Vis光譜描述電子躍遷的特徵峰，此外，通過FCC的單晶X射線衍射分析解釋了FCC結構的平面性較低的對稱性。

通過FCC的高溫熱解後於氧還原反應之電催化劑。在不同熱解溫度下，根據環盤旋轉電極測量，在500 ºC下獲得的電催化劑顯示主要遵循四個電子的氧氣還原途徑。與熱解的鈷咕咯相比，本研究中證明的雙金屬金屬環大錯合物電催化劑顯示出20 mV較高的起始電位。此外，以1:1比例的FCC與炭黑製備的電催化劑在開始和半電位改善方面表現出更好的氧還原活性。

為了更好地了解加強氧還原的催化活性，利用不同的分析技術分析Py-FCC/C-50電催化劑。粉末X光繞射證實了催化劑中鐵三碳(Fe3C)的形成，並且通過拉曼分析，還觀察到石墨碳的清楚鑑定。X光光電子能譜分析顯示鐵碳鍵與鈷氮鍵的形成，並利用顯微技術，如SEM和TEM，顯示在石墨碳載體上具有2-3 nm尺寸的納米金屬顆粒。更重要的是，FT-IR光譜顯示在500 ºC下FCC熱解後保存了1038 cm-1的Co-N大環振動帶，證實了氧還原活性位點作為CoN4與碳化鐵一起存在。最後，提出了電催化劑遵循4-電子氧還原途徑的機理。Py-FCC/C-50所顯示的電子轉移數約為3.98，H2O2產率小於2.3%，與商業Pt/C幾乎相似，遠優於熱解的鈷咕咯。發現Py-FCC/C-50催化劑的穩定性在2000次電化學循環後的半電位僅減少10 mV。

This thesis demonstrates the synthesis of a novel binary non-precious metals (Co & Fe) incorporated in a single metal-N4 corrole macrocycle complex (FCC), elucidating its lower symmetric character by single crystal X-ray diffraction analysis and its pyrolyzed form as an electrocatalyst for enhanced oxygen reduction reaction (ORR) for fuel cell application.

The challenging multistep synthesis of FCC is successfully described despite the fact of directly attached electron rich ferrocene group onto the 10-meso-carbon of corrole and its less interaction with corrole ring. The methodologies to overcome troublesome purification and yield improvements of FCC are also briefly illustrated. The complex FCC structure was confirmed by well resolved 1H, 13C NMR and FT-IR spectra. The characteristic bands of electronic transitions appeared for corrole such as soret and Q-bands of FCC were described by using UV-Vis spectroscopy. In addition, the lower symmetry and distortion in planarity of FCC structure were explained by single crystal X-ray diffraction analysis.

The FCC derived electrocatalysts for ORR application were obtained by high temperature pyrolysis of FCC. The fabrication process of electrocatalyst preparation and its deposition on glassy carbon working electrode for electrochemical study are described in the later sections of the thesis. The optimized electrocatalyst with improved ORR activity by designing different experimental methods are demonstrated. According to FCC derived catalysts developed at different temperatures, the electrocatalyst obtained at 500 ºC showed to follow mostly a four electron O2 reduction pathway according to RRDE measurements. The bimetallic metal-N4 electrocatalyst demonstrated in this study showed 20 mV higher onset potentials as compared to pyrolyzed Co-corroles. Further, the electrocatalyst prepared with 1:1 weight ratio of FCC to carbon black showed the better ORR activity in terms of improved onset and half-wave potential.

To know the better insight of understanding the catalytic active sites for enhanced ORR, different analytical techniques were utilized to analyze Py-FCC/C-50 electrocatalyst. The powder XRD demonstrated the formation of iron carbide phase in the catalyst, and including with Raman analysis, the clear identification of graphitic carbon was also observed. The XPS analysis displayed the slight evidence of C-Fe bonding signature by C 1s and Fe 2p, which partly supports the powder XRD data. The existence of CoNx bonding structure was confirmed with both N 1s and Co 2p deconvoluted XPS spectra. SEM and TEM microscopic data revealed the uniform distribution of nanoparticle of 2-3 nm sizes on the graphitic carbon support. More importantly, the FT-IR spectra revealed the preservation of Co-N macrocycle vibrational band of 1038 cm-1 after FCC pyrolysis at 500 ºC, confirming the presence of ORR active site as CoN4 together with iron carbide. These observed closely distributed active sites together could be the reason to show the enhanced four electron ORR pathway reaction. Eventually, the mechanism by which the electrocatalyst follows the 4-electron oxygen reduction pathway was proposed. The electron transfer number exhibited by Py-FCC/C-50 is around 3.98 with less than 2.3% H2O2 yield, which are nearly similar to the commercial Pt/C and much better than pyrolyzed Co-corroles. Electrochemical ORR stability of Py-FCC/C-50 catalyst was found to be only 10 mV loss in half-wave potentials after 2000 LSV cycles.

Acknowledgements…………………………………………………………………....................... i
Abstract……………………………………………………………………...........................………… iii
List of Abbreviations…………………………………………………………....................…….. xii

Chapter 1
Introduction......................................................................................................................... 1
1.1. Renewable energy sources ................................................................................... 1
1.2. Polymer electrolyte membrane fuel cells (PEMFC) ..................................... 2
1.3. Cathode electrocatalyst of PEMFC .................................................................... 3
1.4. Macrocyclic N4 molecules for oxygen reduction ........................................ 5
1.4.1. ORR by nature in biological systems ..............................................................5
1.4.2. Macrocycle metal-N4 for ORR ..........................................................................7
1.5. Strategies for FCC target objectives ................................................................. 8
1.5.1. Lower symmetry macrocycle metal-N4 for ORR .......................................8
1.5.2. Cobalt and iron macrocycle metal-N4 complexes for ORR ..................9
1.5.3. Mixed-bimetal single molecular macrocyclic-N4 complex of lower symmetry .......................................................................................................................... 10
1.6. Corrole complexes ................................................................................................ 11
1.7. Motivation of FCC synthesis for ORR ............................................................. 12

Chapter 2
Synthesis and yield improvements of FCC ........................................................... 14
2.1. Synthesis of FCC ..................................................................................................... 14
2.1.1. Methodology to prepare 10-ferrocenyl-5,15-diphenyl
corrole (1) .......................................................................................................................... 14
2.1.2. Methodology for FCC (2) synthesis ............................................................. 15
2.1.3. General techniques and materials ............................................................... 17
2.1.4. Synthesis of 5-phenyldipyrromethane ...................................................... 18
2.1.5. Synthesis procedure of 10-ferrocenyl-5,15-diphenyl corrole (1) .... 18
2.1.6. Synthesis procedure of FCC (2) ..................................................................... 19
2.2. Purification methods for FCC............................................................................. 20
2.3. Challenges of FCC purification by column chromatography ............... 22
2.4. Optimization process to improve purity and yields of FCC .................. 23
2.5. Single crystal formation of FCC ........................................................................ 26
2.6. Summary ................................................................................................................... 27

Chapter 3
Characterization of FCC ............................................................................................... 28
3.1. Materials and instrumentation ......................................................................... 28
3.2. NMR and FT-IR spectroscopy ........................................................................... 29
3.3. UV-Visible absorption spectrum of FCC ....................................................... 31
3.4. Single crystal X-ray diffraction analysis ......................................................... 32
3.4.1. Bond angles .......................................................................................................... 35
3.4.2. Bond distances .................................................................................................... 36
3.4.3. Torsional angles .................................................................................................. 37
3.5. Summary ................................................................................................................... 39

Chapter 4
Preparation of FCC electrocatalyst and electrochemical ORR study
4.1. Materials and instrumentation ......................................................................... 40
4.2. Electrochemical measurements ....................................................................... 41
4.3. Thermogravimetric analysis of FCC ................................................................ 42
4.4. Preparation process of electrocatalyst .......................................................... 43
4.4.1. Electrocatalyst development by thermal CVD process........................ 43
4.4.2. Electrocatalyst ink deposition method on GCE ...................................... 44
4.5. Cyclic Voltammetry ............................................................................................... 45
4.6. Design of experimental setup for ORR measurements .......................... 46
4.6.1. Different pyrolysis temperatures study for ORR .................................... 47
4.6.2. Evaluation of Py-FCC/C ORR activity .......................................................... 49
4.6.3. Acid leaching ....................................................................................................... 51
4.6.4. High loading of FCC precursor ..................................................................... 53
4.7. Summary ................................................................................................................... 55

Chapter 5
Discussion and understanding of FCC electrocatalyst .................................... 56
5.1. Materials and instrumentation ......................................................................... 56
5.2. Results and discussion ......................................................................................... 57
5.2.1. Electrochemical surface area measurements .......................................... 57
5.2.2. ICP-MS and elemental analysis .................................................................... 59
5.2.3. Powder X-ray diffraction and Raman spectroscopy analysis ............ 60
5.2.4. X-ray photoelectron spectroscopy analysis ............................................. 62
5.2.5. SEM and TEM characterization ..................................................................... 64
5.2.6. FT-IR and MALDI-TOF mass spectroscopy analysis .............................. 65
5.3. Proposed mechanism .......................................................................................... 68
5.4. Comparison of ORR activity ............................................................................... 69
5.4.1. RRDE measurements ........................................................................................ 69
5.4.2. Koutecky–Levich (K-L) plot by RDE measurements .............................. 71
5.5. Stability study .......................................................................................................... 72
5.6. Schematic overview of FCC for ORR ............................................................... 73
5.7. Summary ................................................................................................................... 74

Chapter 6
Conclusion and future perspectives ....................................................................... 75
6.1. Conclusions .............................................................................................................. 75
6.2. Future perspectives ............................................................................................... 77

References ........................................................................................................................ 79

Supporting information .............................................................................................. 89

Appendix: Co-triazole MOF derived electrocatalyst for ORR .................... 100

List of publications ...................................................................................................... 103

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