Display options
Cite
van der Meijden MW, Gelens E, Quirós NM, et al. Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene. Chemistry. 2015;22(4):1484-92doi: 10.1002/chem.201502798.
van der Meijden, M. W., Gelens, E., Quirós, N. M., Fuhr, J. D., Gayone, J. E., Ascolani, H., Wurst, K., Lingenfelder, M., & Kellogg, R. M. (2016). Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene. Chemistry (Weinheim an der Bergstrasse, Germany), 22(4), 1484-92. https://doi.org/10.1002/chem.201502798
van der Meijden, Maarten W, et al. "Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,4 (2016): 1484-92. doi: https://doi.org/10.1002/chem.201502798
van der Meijden MW, Gelens E, Quirós NM, Fuhr JD, Gayone JE, Ascolani H, Wurst K, Lingenfelder M, Kellogg RM. 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. PMID: 26662511.
Copy Download .nbib Format: NLM
Share it on

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

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

Chemistry (Weinheim an der Bergstrasse, Germany)

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

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. [email protected].
  7. Syncom BV, Kadijk 3, 9747, AT Groningen, The Netherlands. [email protected].

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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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

Publication Types