Heteroatom-Doped Perihexacene from a Double Helicene Precursor: On-Surface Synthesis and Properties.
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.
Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
Xiao-Ye
0000-0003-3540-0277
XY
Wang
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Thomas
0000-0001-8146-8841
T
Dienel
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Marco
M
Di Giovannantonio
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Gabriela Borin
GB
Barin
Department of Physics, Rensselaer Polytechnic Institute , Troy, 12180 New York, United States.
Neerav
N
Kharche
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Okan
0000-0001-8634-8849
O
Deniz
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
José I
JI
Urgel
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Roland
R
Widmer
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Samuel
S
Stolz
Paul Scherrer Institut , 5232 Villigen PSI, Switzerland.
Luis Henrique
LH
De Lima
Paul Scherrer Institut , 5232 Villigen PSI, Switzerland.
Matthias
M
Muntwiler
Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'G. Natta', Politecnico di Milano , Piazza Leonardo da Vinci 32, 20133 Milano, Italy.
Matteo
0000-0002-7917-426X
M
Tommasini
Department of Physics, Rensselaer Polytechnic Institute , Troy, 12180 New York, United States.
Vincent
V
Meunier
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
Pascal
0000-0001-5729-5354
P
Ruffieux
Center for Advancing Electronics Dresden, Department of Chemistry and Food Chemistry, Technische Universität Dresden , 01062 Dresden, Germany.
Xinliang
X
Feng
Empa, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.|Department of Chemistry and Biochemistry, University of Bern , 3012 Bern, Switzerland.
Roman
R
Fasel
Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
Klaus
0000-0001-6630-8786
K
Müllen
Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
Akimitsu
0000-0002-3625-522X
A
Narita