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Synthesis of 2D Polymer Using Chemical Reaction on Surfaces
Tobe LaboratoryKyohei Kaneko
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Contents• Introduction ・ Concept of 2D Polymer ・ Graphene ・ Chemical Reaction on The Surface
• Observation Conditions of STM ・ Liquid/Solid Interface vs. Ultra High Vacuum (UHV)
• Previous Researches toward The Synthesis of 2D Polymer
• My Study• Conclusion
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What is 2D Polymer ?
Schlüter, D. et.al. Angew. Chem. Int. Ed. 2009, 48, 1030 – 1069.
2D Polymer
Polymer
Fascinating Properties
● strength● elasticity● electric conductivity
ex) polyethylene terephthalate (PET)
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An Example of 2D Polymer -Graphene-
Graphite
GrapheneNobel Prize in Physics (2010)
Carbon Atom
● thickness of single carbon atom● high strength● very fast electron transfer
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Chemical Reaction on The Surface
Chemical Reaction on The SurfaceAtom ormolecule(0.1~5 nm)
Defect of Graphene× Fabrication in the nano scale× Flexibility of chemical modification
Chemical Reaction
2D Polymer
Covalent Bond
・ Bottom-up approach・ Flexibility of chemical modification
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Observation Conditions of STM
@Tobe lab.
Nanoscope IIIa (Digital Instruments)
PicoSTM (Agilent)
Interface experiments: ■ measurements under ambient conditions ■ easy manipulation ■ simple (and less expensive) equipment ■ limited temperature range ■ dynamic behavior (sometimes disadvantage)
UHV Conditions: ■ wide temperature range ■ electronic state information (I/V response) ■ free from complexity due to solvents ■ hard manipulation ■ atoms or molecules must be evaporated to deposit surface (蒸着) .
Liquid/Solid Interface Ultra High Vacuum (UHV)
Graphite
Sample solution
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Previous Research Ⅰ
Müllen, K.; Fasel, R. et al. Nature 2010, 466, 470-473.
Graphene Nano Ribbon (GNR)
On Au(111) under UHV condition
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Previous Research Ⅱ
On Ag(111) under UHV condition
After annealing at 805 K.
M. Bieri, R. Fasel, et al. Chem. Commun. 2009, 6919-6921.
Porous network
Cyclohexa-m-phenylene(CHP)
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Previous Research Ⅲ
On Ag(111) under UHV condition
Fe Atom
Abel, M. ; Clair, S. et al. J. Am. Chem. Soc. 2011, 133, 1203-1205.
1,2,4,5-tetracyanobenzene
(TCNB)
On a thin insulating NaCl island deposited on Ag(100)
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My StudyPurpose of This Work
Functional Group
Self-Assembly
Guest Molecule
Chemical Reaction
Covalent Bond
Dehydrobenzo[12]annulene(DBA)
Honeycomb Structure
Self-Assembly
Guest Molecule
Host-Guest Co-adsorption
2D Polymer
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NH2 CHO
nBuOH
NCH
HOnBu
Imine-Forming Reaction
InvertibleAmine Aldehyde Imine
Target Molecule
Alkyl Chain Interdigitation
Honeycomb Network of DBA 1
Amine
2
Imine–Forming Reaction
Imine Bond
Molecular Network of DBA 1 and Aldehyde 2
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Conclusion• Intense interests have been paid for the synthesis and physical
properties of the 2D polymer which constitutes ordered nano structure with single atomic film thickness, and which is novel polymeric material.
• One of the methods for the synthesis of 2D polymer is utilizing the chemical reaction on solid surfaces, and unique 2D polymer have been synthesized recently.
• In my project, I’ll synthesize 2D polymer via imine formation between the DBA which comprises amino groups at the end of alkyl chains and guest molecule with the formyl groups at the ambient condition.