Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene

Maarten W van der Meijden; Edith Gelens; Natalia Murillo Quirós; Javier D Fuhr; J Esteban Gayone; Hugo Ascolani; Klaus Wurst; Magalí Lingenfelder; Richard M Kellogg

doi:10.1002/chem.201502798

Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene

Chemistry. 2016 Jan 22;22(4):1484-92. doi: 10.1002/chem.201502798. Epub 2015 Dec 14.

Authors

Maarten W van der Meijden¹, Edith Gelens², Natalia Murillo Quirós^{3

4}, Javier D Fuhr³, J Esteban Gayone³, Hugo Ascolani³, Klaus Wurst⁵, Magalí Lingenfelder⁶, Richard M Kellogg⁷

Affiliations

¹ Syncom BV, Kadijk 3, 9747, AT Groningen, The Netherlands.
² Nano Fiber Matrices B.V., Zernikepark 6, 9747, AN Groningen, The Netherlands.
³ Centro Atómico Bariloche, CNEA and CONICET, Av. E. Bustillo km. 9.500, R8402AGP, San Carlos de Bariloche, Argentina.
⁴ Instituto Tecnologico de Costa Rica, A-4, Tecnológico de Costa Rica, Cartago, Costa Rica.
⁵ Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.
⁶ Institut de Physique de la Matière Condensée, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland. magali.lingenfelder@epfl.ch.
⁷ Syncom BV, Kadijk 3, 9747, AT Groningen, The Netherlands. r.m.kellogg@syncom.nl.

PMID: 26662511
DOI: 10.1002/chem.201502798

Abstract

A convergent synthesis of racemic 5-amino[6]hexahelicene is described. Cross-coupling reactions are used to assemble a pentacyclic framework, and a metal-catalyzed ring-closure comprises the final step. The enantiomers were separated by means of chromatography and the absolute configurations were assigned by comparison of the CD spectra with hexahelicene. The t1/2 value for racemization at 210 °C was approximately 1 hour. Scanning tunneling microscopy (STM) measurements were carried out on enantiopure and racemic samples of aminohelicene on Au(111) under ultrahigh vacuum (UHV) conditions.

Keywords: cross-coupling; helicenes; optical properties; resolution; scanning tunneling microscopy.

Publication types

Research Support, Non-U.S. Gov't