TY - JOUR
T1 - Heteroatom-Doped Perihexacene from a Double Helicene Precursor
T2 - On-Surface Synthesis and Properties
AU - Wang, Xiao Ye
AU - Dienel, Thomas
AU - Di Giovannantonio, Marco
AU - Barin, Gabriela Borin
AU - Kharche, Neerav
AU - Deniz, Okan
AU - Urgel, José I.
AU - Widmer, Roland
AU - Stolz, Samuel
AU - De Lima, Luis Henrique
AU - Muntwiler, Matthias
AU - Tommasini, Matteo
AU - Meunier, Vincent
AU - Ruffieux, Pascal
AU - Feng, Xinliang
AU - Fasel, Roman
AU - Müllen, Klaus
AU - Narita, Akimitsu
N1 - Funding Information:
We acknowledge the financial support from Max Planck Society and European Commission through the FET-Proactive Project “MoQuaS”, contract no. 610449, the Graphene Flagship and the Swiss National Science Foundation. The XPS experiments were performed on the X03DA (PEARL) beamline at the Swiss Light Source, Paul Scherrer Institut, Villigen, Switzerland. Lukas Rotach is acknowledged for technical support. Xiao-Ye Wang is grateful for the fellowship from Alexander von Humboldt Foundation.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/4/5
Y1 - 2017/4/5
N2 - We report on the surface-assisted synthesis and spectroscopic characterization of the hitherto longest periacene analogue with oxygen-boron-oxygen (OBO) segments along the zigzag edges, that is, a heteroatom-doped perihexacene 1. Surface-catalyzed cyclodehydrogenation successfully transformed the double helicene precursor 2, i.e., 12a,26a-dibora-12,13,26,27-tetraoxa-benzo[1,2,3-hi:4,5,6-h′i′]dihexacene, into the planar perihexacene analogue 1, which was visualized by scanning tunneling microscopy and noncontact atomic force microscopy. X-ray photoelectron spectroscopy, Raman spectroscopy, together with theoretical modeling, on both precursor 2 and product 1, provided further insights into the cyclodehydrogenation process. Moreover, the nonplanar precursor 2 underwent a conformational change upon adsorption on surfaces, and one-dimensional self-assembled superstructures were observed for both 2 and 1 due to the presence of OBO units along the zigzag edges.
AB - We report on the surface-assisted synthesis and spectroscopic characterization of the hitherto longest periacene analogue with oxygen-boron-oxygen (OBO) segments along the zigzag edges, that is, a heteroatom-doped perihexacene 1. Surface-catalyzed cyclodehydrogenation successfully transformed the double helicene precursor 2, i.e., 12a,26a-dibora-12,13,26,27-tetraoxa-benzo[1,2,3-hi:4,5,6-h′i′]dihexacene, into the planar perihexacene analogue 1, which was visualized by scanning tunneling microscopy and noncontact atomic force microscopy. X-ray photoelectron spectroscopy, Raman spectroscopy, together with theoretical modeling, on both precursor 2 and product 1, provided further insights into the cyclodehydrogenation process. Moreover, the nonplanar precursor 2 underwent a conformational change upon adsorption on surfaces, and one-dimensional self-assembled superstructures were observed for both 2 and 1 due to the presence of OBO units along the zigzag edges.
UR - http://www.scopus.com/inward/record.url?scp=85016966845&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85016966845&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b02258
DO - 10.1021/jacs.7b02258
M3 - Article
C2 - 28335591
AN - SCOPUS:85016966845
SN - 0002-7863
VL - 139
SP - 4671
EP - 4674
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 13
ER -