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Title Page

Abstract

Contents

1. Research background for Two-Dimensional Materials Nano-reactor 9

1.1. Chemistry at high pressure 9

1.2. Chemical reactivity under nanoconfinement 12

1.3. Van der Waals pressure between the layers of 2D materials 15

1.4. Research objectives and approaches 17

2. Organic reactions via confinement between layers of 2D Materials 18

2.1. Introduction 18

2.2. Experimental Process 24

2.2.1. Cyclodehydrogenation of HPB in confined 2D material vessel 24

2.2.2. Ni deposition on the 2D material confined vessel 24

2.2.3. Characterization 24

2.2.4. Theoretical calculations 25

2.3. Results and discussions 28

2.3.1. Characterization of cyclodehydrogenation of HPB in 2D nano-reactor 28

2.3.2. High-resolution TEM analysis of HPB and HBC in a confined graphene vessel 36

2.3.3. Theoretical calculations 40

3. Conclusion 45

References 46

List of Figures

Figure 1.1.1. Schematic illustration of chemistry under high pressure. 11

Figure 1.2.1. Schematic illustration of diverse confined systems. 14

Figure 1.3.1. Schematic illustration of water between layers of graphene. 16

Figure 2.1.1. Schematic illustration of cyclodehydrogenation of HPB confined between graphene layers. 20

Figure 2.1.2. Controlled experiments to verify the effect of pressure under the reaction condition to form HBC from HPB. HPB was heated at 200℃ for 180 min in air and solution. 21

Figure 2.1.3. STM images of HPB molecules on Au(111) surface after annealing at different temperatures. 22

Figure 2.1.4. STM images of HPB molecules deposited on Au(111) surface maintained at 200, 300, and 400 ℃. 23

Figure 2.2.1. Schematic illustration of G/HPB/G sample preparation process and AFM images and height profile of graphene and HPB-Graphene on SiO₂(300nm)/Si wafer. 26

Figure 2.2.2. Schematic illustration of peeling of graphene or hBN layers by Ni deposition on both sides of the vessel. 27

Figure 2.3.1. Temperature-dependent Raman spectra of G/HPB/G spin-coated with 2, 1, 0.5 and 0.1 mg mL⁻¹ HPB solutions. 30

Figure 2.3.2. Cyclodehydrogenation reaction of HPB between layers of graphene or hBN. 32

Figure 2.3.3. TOF-SIMS spectra of HPB and HBC between graphene or hBN layers before and after heat treatment. 33

Figure 2.3.4. Raman and TOF-SIMS spectra of G/HBC(commercial)/G. 34

Figure 2.3.5. Orbitrap™-SIMS spectra and TOF-SIMS spectra of HPB/G without a top graphene layer. 35

Figure 2.3.6. High-resolution TEM images of HPB and HBC in a confined graphene vessel after annealing G/HPB/G at 150 ℃ for 180 min. 37

Figure 2.3.7. High-resolution TEM images of HPB and HBC in confined graphene vessels after annealing G/HPB/G at 100 ℃ for 180 min. 38

Figure 2.3.8. High-resolution TEM analysis of HBC in confined 2D material vessels. 39

Figure 2.3.9. Reaction energy profile and corresponding optimised structures for the first cyclodehydrogenation reaction of HPB confined in graphene layers based on the density... 41

Figure 2.3.10. Force component acting on the sandwiched HPB in the optimised hBN/HPB/hBN and G/HPB/G structures. 42

Figure 2.3.11. Reaction energy profiles for the synchronous and stepwise cyclodehydrogenation reactions based on the density functional theory calculations. 44

초록보기

 Confinement of reactants within nanoscale spaces of low dimensional materials have big implications in chemistry, because chemical reactions conducted at high pressures provide opportunities for realizing new synthesis chemistries and achieving novel states of matter. Compared with 0D (zero-dimensional) and 1D confined spaces, well-defined confined van der Waals (vdW) gap spaces between 2D materials offer simplicity, scalability and well-controlled pressure due to upward and downward forces only. While studies have been carried out using 0D and 1D confined spaces found in pores of zeolites and carbon nanotubes, organic reactions in 2D confined spaces have yet to be explored. Herein, we report new solid-state organic reactions induced by high pressure between graphene (and hBN) layers. We also provide detailed analysis for the mechanisms involved. We demonstrate that graphene (or hBN) sandwich structures can be used to confine reactants under high (up to 7 GPa) van der Waals pressure. As a proof of concept, we show the cyclodehydrogenation of hexaphenylbenzene, which is well-known strategy for syntheses of polycyclic aromatic hydrocarbons, in 2D materials confined space. While this reaction does not occur in bulk solution or powder, nanoconfinement effect by high pressure in 2D confined vessels enable this reaction at the same conditions. Our approach is facile and general for solid-state organic reactions. In addition, our product itself (graphene/product/graphene or hBN/product/hBN) can be used in on-demand applications, which is different from unutilized products on catalytic metal surfaces.

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