傳統半導體設計已經逼近物理極限，並且在原子尺度上的精確設計上面臨許多的挑戰。由分子及原子蒸鍍在基板上自下而上的方式提供了製造更小元件的可能性。從分子建構單元生長二維材料表面是最近熱門的領域。分子電子元件的發展取決於我們對局域性的物理化學機制了解以及調控及合成鍵合的開發。在此篇論文中，掃描穿隧式顯微鏡技術被應用在探討分子表面自組裝, 表面催化共價耦合跟有機金屬鍵的系統上。延展Pi電子網絡對於物理、化學、材料、元件製造上都是很有趣的課題。在此，我們給出了各類新合成Pi電子網絡分子在不同基板系統中的結果。

Traditional semiconductor structure fabricated by top-down approach are reaching
intrinsic physical limits. A Bottom-up approach through the deposition of
atoms, molecules provides the prospects of smaller device designs. The synthesis
of extended but atomically defined nanostructures from molecular building
blocks in the vicinity of a two-dimensional surface is a strongly emerging field of
research. Progress towards single-molecule electronics relies on a thorough understanding
of local physio-chemical processes and development of synthetic route for
controlled hetero-coupling. In this thesis, STM (Scanning Tunneling Microscopy)
is used to study the growth behavior of molecular self-assembly, surface-assited
coupling reactions and metal-organic formation on metallic surfaces. Extended -
electron molecular networks are of much interest in chemistry, physics, materials
science and device application. Here, the result of a multitude of newly synthesized
molecules are presented.

1 Overview of Scanning Tunneling Microscope 4
1.1 Theory and Working Principle . . . . . . . . . . . . . . . . . . . . . 4
1.1.1 Quantum tunneling in a one dimensional system . . . . . . . 6
1.1.2 Bardeen’s tunneling theory . . . . . . . . . . . . . . . . . . . 7
1.1.3 Tersoff-Hamann model[2] . . . . . . . . . . . . . . . . . . . . 11
1.2 Experimental Apparatus . . . . . . . . . . . . . . . . . . . . . . . . 12
1.2.1 Overview of experimental setup . . . . . . . . . . . . . . . . 12
1.2.2 Ultra-High Vacuum . . . . . . . . . . . . . . . . . . . . . . . 13
1.2.3 Liquid nitrogen temperature . . . . . . . . . . . . . . . . . . 16
1.2.4 Sample storage and transfer . . . . . . . . . . . . . . . . . . 17
1.2.5 Sample preparation . . . . . . . . . . . . . . . . . . . . . . . 17
1.2.6 Scanning Tunneling Microscopy . . . . . . . . . . . . . . . . 19
2  Conjagated Systems: Phenacene Assemblies 22
2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.2 Methods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
2.3 Results . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2.3.1 Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2.3.2 Unsubstituted Phenacenes: General Growth Behavior . . . . 31
2.3.3 Monolayer Coverage - Unsubstituted Phenacenes . . . . . . 33
2.3.4 Monolayer Coverage - substituted Phenacenes . . . . . . . . 34
2.3.5 Bilayer Growth . . . . . . . . . . . . . . . . . . . . . . . . . 37
2.3.6 Electronic structure: STS on second monolayer . . . . . . . 40
3 Surface Assisted Coupling 47
3.1 PAL molecule . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
3.1.1 PAL on Ag(100) . . . . . . . . . . . . . . . . . . . . . . . . 49
3.1.2 PAL on Au(111) . . . . . . . . . . . . . . . . . . . . . . . . 51
3.1.3 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . 52
3.2 2Br-PIC(2-Br-[5]phenacene) . . . . . . . . . . . . . . . . . . . . . . 54
3.2.1 2,2’-BiPicenyl through On-Surface Synthesis . . . . . . . . . 54
3.2.2 2,2’-BiPicenyl from Molecular Powder . . . . . . . . . . . . . 57
3.3 4Br-PIC(4-Br-[5]phenacene) . . . . . . . . . . . . . . . . . . . . . . 59
3.3.1 4Br-PIC on Au(111) . . . . . . . . . . . . . . . . . . . . . . 60
3.3.2 Structure evolution with temperature . . . . . . . . . . . . . 61
3.3.3 Electronic properties with structure . . . . . . . . . . . . . . 65
3.3.4 Discussion and Summary . . . . . . . . . . . . . . . . . . . . 69
3.3.5 Supplement 1: Overview of presented data . . . . . . . . . . 70
3.3.6 Supplement 2: Structural Evolution of molecular system
with temperature as recorded in LEED . . . . . . . . . . . . 71
3.3.7 Supplement 3: Sample and Film Preparation. . . . . . . . . 73
3.3.8 Supplement 4: STM and STS parameters . . . . . . . . . . . 75
3.3.9 Supplement 5: FFT-STM - Technical Notes . . . . . . . . . 75
3.3.10 Supplement 6: Extended Experimental Results . . . . . . . . 76
3.3.11 Supplement 7: Synchrotron Setup . . . . . . . . . . . . . . . 77
3.4 3,10-Bis(bromo)picene vs. 3,10-Bis(bromomethyl)picene . . . . . . . 78
3.4.1 3,10-Bis(bromo)picene on Au(111) . . . . . . . . . . . . . . . 79
3.4.2 3,10-Bis(bromomethyl)picene on Au(111) . . . . . . . . . . . 80
3.4.3 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
4 Metal Organic Coordination Complex 88
4.1 PCAH . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89
4.1.1 Result . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89
4.1.2 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
4.2 Pyrenyl-DiKetone-Phenyl . . . . . . . . . . . . . . . . . . . . . . . 94
4.2.1 Preparation . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
4.2.2 Molecule Absoprtion . . . . . . . . . . . . . . . . . . . . . . 95
2
4.2.3 Cobalt Metal with Molecule . . . . . . . . . . . . . . . . . . 98
4.2.4 Annealing Induced Metal Coordination . . . . . . . . . . . . 101
4.2.5 Scanning Tunneling Spectroscopy . . . . . . . . . . . . . . . 105
4.3 Pb+PyDKPh+surface annealing . . . . . . . . . . . . . . . . . . . . 106
4.3.1 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . 109
5 Summary 114
3

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