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Synthesis and characterization of triangulene

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Pavliček, Niko, Mistry, Anish, Majzik, Zsolt, Moll, Nikolaj, Meyer, Gerhard, Fox, David J. and Gross, Leo (2017) Synthesis and characterization of triangulene. Nature Nanotechnology, 12 . 308-311 . doi:10.1038/nnano.2016.305 ISSN 1748-3387.

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Official URL: http://dx.doi.org/10.1038/nnano.2016.305

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Abstract

Triangulene, the smallest triplet-ground-state polybenzenoid (also known as Clar's hydrocarbon), has been an enigmatic molecule ever since its existence was first hypothesized1. Despite containing an even number of carbons (22, in six fused benzene rings), it is not possible to draw Kekulé-style resonant structures for the whole molecule: any attempt results in two unpaired valence electrons2. Synthesis and characterization of unsubstituted triangulene has not been achieved because of its extreme reactivity1, although the addition of substituents has allowed the stabilization and synthesis of the triangulene core3, 4 and verification of the triplet ground state via electron paramagnetic resonance measurements5. Here we show the on-surface generation of unsubstituted triangulene that consists of six fused benzene rings. The tip of a combined scanning tunnelling and atomic force microscope (STM/AFM) was used to dehydrogenate precursor molecules. STM measurements in combination with density functional theory (DFT) calculations confirmed that triangulene keeps its free-molecule properties on the surface, whereas AFM measurements resolved its planar, threefold symmetric molecular structure. The unique topology of such non-Kekulé hydrocarbons results in open-shell π-conjugated graphene fragments6 that give rise to high-spin ground states, potentially useful in organic spintronic devices7, 8. Our generation method renders manifold experiments possible to investigate triangulene and related open-shell fragments at the single-molecule level.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Polycyclic aromatic hydrocarbons -- Synthesis
Journal or Publication Title: Nature Nanotechnology
Publisher: Nature Publishing Group
ISSN: 1748-3387
Official Date: 13 February 2017
Dates:
DateEvent
13 February 2017Published
29 December 2016Accepted
27 September 2016Submitted
Volume: 12
Page Range: 308-311
DOI: 10.1038/nnano.2016.305
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Date of first compliant deposit: 7 March 2017
Date of first compliant Open Access: 13 August 2017
Funder: European Research Council (ERC)
Grant number: CEMAS (agreement no. 291194), AMSEL (682144), PAMS (610446), ITN QTea (317485)

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