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Surface-Dependent Chemoselectivity in C-C Coupling Reactions.

Zhi Chen^1,2, Tao Lin^3,4, Liding Zhang³

¹Institute of Nanotechnology, Karlsruhe Institute of Technology (KIT), 76344, Eggenstein-Leopoldshafen, Germany.

Angewandte Chemie (International Ed. in English)

|April 25, 2019

Summary

This summary is machine-generated.

This study explores surface reactions of a biphenyl compound with alkyne and enyne groups. It reveals surface-dependent chemoselectivity, paving the way for novel carbon-based polymer synthesis.

Keywords:

alkenes alkynes chemoselectivity cross-coupling scanning tunneling microscopy

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Published on: September 12, 2018

Area of Science:

Materials Science
Surface Chemistry
Polymer Chemistry

Background:

Investigating surface-confined covalent coupling reactions is crucial for designing advanced materials.
Understanding the role of functional groups like alkynes and enynes in surface reactions is key.
The synthesis of covalent carbon-based polymers with specific architectures remains a challenge.

Purpose of the Study:

To investigate the surface-confined covalent coupling reactions of 4-(but-3-en-1-ynyl)-4'-ethynyl-1,1'-biphenyl.
To elucidate the surface-dependent chemoselectivity of these reactions on different metal substrates.
To explore the potential for creating novel sp-sp² polymers through surface-confined synthesis.

Main Methods:

Utilized scanning tunneling microscopy (STM) to observe surface reactions at the molecular level.
Employed density functional theory (DFT) calculations to understand reaction mechanisms and selectivity.
Studied the behavior of a linear biphenyl compound with terminal alkyne and enyne functionalities.

Main Results:

Observed distinct surface-dependent chemoselectivity: cyclotrimerization on Au(111) and selective enyne-alkyne coupling on Cu(111).
Formation of linear, V-shaped, and Y-shaped motifs leading to surface reticulation.
DFT calculations identified a critical C-H⋅⋅⋅π transition state governing reaction selectivity.

Conclusions:

The study demonstrates a novel concept for surface-confined synthesis of covalent carbon-based sp-sp² polymers.
Surface chemistry dictates the outcome of coupling reactions, enabling control over polymer architecture.
This approach opens new avenues for creating functional polymeric materials with tailored properties.