SCHEDULED MAINTENANCE
Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization†
a
Steffen
Böckmann,
c
Silvio
Osella,
d
Nicolás
Arisnabarreta,
e
David
Beljonne,
g
Jan J.
Weigand,
f
Mischa
Bonn,
b
Steven
De Feyter,
e
Michael Ryan
Hansen,
c
Hai I.
Wang,
b
Ji
Ma
*ah
and
Xinliang
Feng
*ah
Abstract
Precise synthesis of graphene nanoribbons (GNRs) is of great interest to chemists and materials scientists because of their unique opto-electronic properties and potential applications in carbon-based nanoelectronics and spintronics. In addition to the tunable edge structure and width, introducing curvature in GNRs is a powerful structural feature for their chemi-physical property modification. Here, we report an efficient solution synthesis of the first pyrene-based GNR (PyGNR) with curved geometry via one-pot K-region oxidation and Scholl cyclization of its corresponding well-soluble tetrahydropyrene-based polyphenylene precursor. The efficient A2B2-type Suzuki polymerization and subsequent Scholl reaction furnishes up to ∼35 nm long curved GNRs bearing cove- and armchair-edges. The construction of model compound 1, as a cutout of PyGNR, from a tetrahydropyrene-based oligophenylene precursor proves the concept and efficiency of the one-pot K-region oxidation and Scholl cyclization, which is clearly revealed by single crystal X-ray diffraction analysis. The structure and optical properties of PyGNR are investigated by Raman, FT-IR, solid-state NMR, STM and UV-Vis analysis with the support of DFT calculations. PyGNR exhibits a narrow optical bandgap of ∼1.4 eV derived from a Tauc plot, qualifying as a low-bandgap GNR. Moreover, THz spectroscopy on PyGNR estimates its macroscopic charge mobility μ as ∼3.6 cm2 V−1 s−1, outperforming several other curved GNRs reported via conventional Scholl reaction.
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