TY - JOUR
T1 - Synthesis, properties, and two-dimensional adsorption characteristics of 5-amino[6]hexahelicene
AU - Van Der Meijden, Maarten W.
AU - Gelens, Edith
AU - Quirõs, Natalia Murillo
AU - Fuhr, Javier D.
AU - Gayone, J. Esteban
AU - Ascolani, Hugo
AU - Wurst, Klaus
AU - Lingenfelder, Magalí
AU - Kellogg, Richard M.
N1 - Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/1/22
Y1 - 2016/1/22
N2 - 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. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
AB - 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. Stairway to heaven? In a convergent synthesis of racemic 5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble a pentacyclic framework, with a metal-catalyzed ring closure as the final step. The enantiomers are separated by means of chromatography and the absolute configurations assigned by comparison of the CD spectra with hexahelicene. Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed under ultrahigh vacuum.
KW - cross-coupling
KW - helicenes
KW - optical properties
KW - resolution
KW - scanning tunneling microscopy
UR - http://www.scopus.com/inward/record.url?scp=84954360815&partnerID=8YFLogxK
U2 - 10.1002/chem.201502798
DO - 10.1002/chem.201502798
M3 - Artículo
AN - SCOPUS:84954360815
SN - 0947-6539
VL - 22
SP - 1484
EP - 1492
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 4
ER -