The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes

Anish Mistry; Ben Moreton; Bruno Schuler; Fabian Mohn; Gerhard Meyer; Leo Gross; Antony Williams; Peter Scott; Giovanni Costantini; David J. Fox

doi:10.1002/chem.201404877

The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes

Anish Mistry, Ben Moreton, Bruno Schuler, Fabian Mohn, Gerhard Meyer, Leo Gross, Antony Williams, Peter Scott, Giovanni Costantini, David J. Fox^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

H-Benzo[cd ]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekulé fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5 H-benzo[cd ]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.

Original language	English
Pages (from-to)	2011-2018
Number of pages	8
Journal	Chemistry - A European Journal
Volume	21
Issue number	5
DOIs	https://doi.org/10.1002/chem.201404877
Publication status	Published - 26 Jan 2015

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

Isomerization
Polyaromatic hydrocarbon
Radical
Scanning probe microscopy
Synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

Access to Document

10.1002/chem.201404877

Cite this

@article{1b2a7e0bbc2f4f65aa4632d12b59291e,

title = "The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes",

abstract = "H-Benzo[cd ]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekul{\'e} fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5 H-benzo[cd ]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.",

keywords = "Isomerization, Polyaromatic hydrocarbon, Radical, Scanning probe microscopy, Synthesis",

author = "Anish Mistry and Ben Moreton and Bruno Schuler and Fabian Mohn and Gerhard Meyer and Leo Gross and Antony Williams and Peter Scott and Giovanni Costantini and Fox, {David J.}",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = jan,

day = "26",

doi = "10.1002/chem.201404877",

language = "English",

volume = "21",

pages = "2011--2018",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "5",

}

TY - JOUR

T1 - The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes

AU - Mistry, Anish

AU - Moreton, Ben

AU - Schuler, Bruno

AU - Mohn, Fabian

AU - Meyer, Gerhard

AU - Gross, Leo

AU - Williams, Antony

AU - Scott, Peter

AU - Costantini, Giovanni

AU - Fox, David J.

PY - 2015/1/26

Y1 - 2015/1/26

N2 - H-Benzo[cd ]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekulé fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5 H-benzo[cd ]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.

AB - H-Benzo[cd ]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekulé fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5 H-benzo[cd ]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.

KW - Isomerization

KW - Polyaromatic hydrocarbon

KW - Radical

KW - Scanning probe microscopy

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=84921346748&partnerID=8YFLogxK

U2 - 10.1002/chem.201404877

DO - 10.1002/chem.201404877

M3 - Article

AN - SCOPUS:84921346748

SN - 0947-6539

VL - 21

SP - 2011

EP - 2018

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 5

ER -

The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this