Volume 22, Issue 41 p. 14633-14639
Full Paper

Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of [6]Hexahelicene-7-carboxylic acid

Dr. Maarten W. van der Meijden

Dr. Maarten W. van der Meijden

Syncom BV, Kadijk 3, 9747 AT Groningen, The Netherlands

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Dr. Tatyana Balandina

Dr. Tatyana Balandina

KU Leuven, Department of Chemistry, Division of Molecular Imaging and Photonics, Celestijnenlaan 200F, 3001 Heverlee, Belgium

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Dr. Oleksandr Ivasenko

Dr. Oleksandr Ivasenko

KU Leuven, Department of Chemistry, Division of Molecular Imaging and Photonics, Celestijnenlaan 200F, 3001 Heverlee, Belgium

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Prof. Dr. Steven De Feyter

Prof. Dr. Steven De Feyter

KU Leuven, Department of Chemistry, Division of Molecular Imaging and Photonics, Celestijnenlaan 200F, 3001 Heverlee, Belgium

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Dr. Klaus Wurst

Dr. Klaus Wurst

University of Innsbruck, Institute of General, Inorganic and Theoretical Chemistry, Innrain 80–82, 6020 Innsbruck, Austria

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Prof. Dr. Richard M. Kellogg

Corresponding Author

Prof. Dr. Richard M. Kellogg

Syncom BV, Kadijk 3, 9747 AT Groningen, The Netherlands

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First published: 24 August 2016
Citations: 7

Graphical Abstract

A winding road: A synthesis of 7-carboxyhexahelicene 1 has been developed using a convergent cross-coupling synthesis that provides the 7-methyl derivative in good yield. The methyl group proved to be remarkably recalcitrant to oxidation to the carboxylic acid of 1. Self-assembly of 1 from the liquid on solid Au(111) provided monolayers of well-ordered racemic two-dimensional crystals.

Abstract

A convergent synthesis of racemic [6]hexahelicene-7-carboxylic acid by cross-coupling of a bicyclic and a tricyclic component is described. A metal-catalyzed ring-closure is also a fundamental component of the synthetic approach. Scanning tunneling microscopy (STM) measurements of the racemate self-assembled on Au(111) at liquid–solid interface revealed the formation of ordered racemic 2D crystals.