Heteroatom-Doped Perihexacene from a Double Helicene Precursor: On-Surface Synthesis and Properties
Wang XY, Dienel T, Di Giovannantonio M, Barin GB, Kharche N, Deniz O, Urgel JI, Widmer R, Stolz S, De Lima LH, Muntwiler M, Tommasini M, Meunier V, Ruffieux P, Feng X, Fasel R, Muellen K, Narita A (2017)
Publication Type: Journal article
Publication year: 2017
Journal
Book Volume: 139
Pages Range: 4671-4674
Journal Issue: 13
DOI: 10.1021/jacs.7b02258
Abstract
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.
Involved external institutions
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Eidgenössische Materialprüfungs- und Forschungsanstalt (Empa) / Swiss Federal Laboratories for Materials Science & Technology
Switzerland (CH)
Rensselaer Polytechnic Institute (RPI)
United States (USA) (US)
Paul Scherrer Institute (PSI)
Switzerland (CH)
Politecnico di Milano
Italy (IT)
Technische Universität Dresden
Germany (DE)
Germany (DE)
Eidgenössische Materialprüfungs- und Forschungsanstalt (Empa) / Swiss Federal Laboratories for Materials Science & Technology
Switzerland (CH)
Rensselaer Polytechnic Institute (RPI)
United States (USA) (US)
Paul Scherrer Institute (PSI)
Switzerland (CH)
Politecnico di Milano
Italy (IT)
Technische Universität Dresden
Germany (DE)
How to cite
APA:
Wang, X.-Y., Dienel, T., Di Giovannantonio, M., Barin, G.B., Kharche, N., Deniz, O.,... Narita, A. (2017). Heteroatom-Doped Perihexacene from a Double Helicene Precursor: On-Surface Synthesis and Properties. Journal of the American Chemical Society, 139(13), 4671-4674. https://doi.org/10.1021/jacs.7b02258
MLA:
Wang, Xiao-Ye, et al. "Heteroatom-Doped Perihexacene from a Double Helicene Precursor: On-Surface Synthesis and Properties." Journal of the American Chemical Society 139.13 (2017): 4671-4674.
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