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 - 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 - https://www.scopus.com/pages/publications/85016966845
UR - https://www.scopus.com/pages/publications/85016966845#tab=citedBy
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 -