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Molecular On-Surface Synthesis: Metal Complexes, Organic Molecules, and Organometallic Compounds

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On-Surface Synthesis

Part of the book series: Advances in Atom and Single Molecule Machines ((AASMM))

Abstract

This article covers aspects of the on-surface synthesis of large molecular systems, in particular metal complexes, organometallic compounds, and organic molecules. It is shown that this approach is especially useful if the desired molecular species are too large or thermally unstable for vapor deposition, or when their synthesis in solution is not possible. Another advantage is the possible formation of well-ordered two-dimensional network structures with a hybrid covalent/van der Waals bonding scheme. The first part of the article focuses on the on-surface synthesis of metalloporphyrins, metallocorroles, and metallophthalocyanines by direct metalation of the respective ligand molecules with coadsorbed metal atoms. The underlying metalation reaction proceeds with high yields and without by-products except hydrogen, which readily desorbs. The second part is devoted to the on-surface synthesis of hydrocarbon macrocycles by means of the surface Ullmann reaction and also discusses the organometallic reaction intermediates with C–Cu–C bonds.

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Abbreviations

CV:

Cyclic voltammetry

DFT:

Density functional theory

EC-STM:

Electrochemical scanning tunneling microscopy

LDOS:

Local density of states

LT-STM:

Low-temperature scanning tunneling microscopy

MOCN:

Metal-organic coordination network

NEXAFS:

Near-edge X-ray absorption fine structure

RT:

Room temperature

SERRS:

Surface-enhanced resonance Raman scattering

STM:

Scanning tunneling microscopy

STS:

Scanning tunneling spectroscopy

TPD:

Temperature programmed desorption

TPR:

Temperature programmed reaction

UHV:

Ultra-high vacuum

UPS:

Ultraviolet photoelectron spectroscopy

XPS:

X-ray photoelectron spectroscopy

DABCO:

1,4-diazabicyclo[2.2.2]octane

DMTP:

4,4″-dibromo-m-terphenyl

DPP:

5,15-diphenylporphyrin

MTP:

meta-terphenyl biradical

OEP:

2,3,7,8,12,13,17,18-octaethylporphyrin

P:

Porphin

Pc:

Phthalocyanine

PPIX:

Protoporphyrin IX (3,7,12,17-tetramethyl-8,13-divinyl-2,18-porphindipropionic acid)

TBPP:

5,10,15,20-tetrakis-(3,5-di-tert-butyl)-phenylporphyrin

TBrPP:

5,10,15,20-tetrakis(4-bromophenyl)porphyrin

TCNB:

1,2,4,5-tetracyanobenzene

TMP:

Meso-tetramesitylporphyrin (5,10,15,20-tetrakis(2,4,6-trimethyl)phenylporphyrin)

TMPA:

5,10,15,20-tetrakis[4-(trimethylammonio)phenyl]-porphyrin

TMPyP4+ :

5,10,15,20-tetra(N-methyl-4-pyridinium)porphyrin

TPCN:

5,10,15,20-tetra[(4-cyanophenyl)phen-4-yl]porphyrin

TPP:

5,10,15,20-tetraphenylporphyrin

TPyP:

5,10,15,20-tetra(4-pyridyl)porphyrin

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Michael Gottfried, J. (2016). Molecular On-Surface Synthesis: Metal Complexes, Organic Molecules, and Organometallic Compounds. In: Gourdon, A. (eds) On-Surface Synthesis. Advances in Atom and Single Molecule Machines. Springer, Cham. https://doi.org/10.1007/978-3-319-26600-8_7

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