Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling

Polyaromatic hydrocarbons can be precisely manipulated to yield ever more complex and discrete graphene analogs, such as nanographenes. Here, the authors use azomethine ylide homocoupling to insert an antiaromatic pyrazine ring into the core of a nanographene, and characterize the molecule’s unique...

Full description

Bibliographic Details
Main Authors: Xiao-Ye Wang, Marcus Richter, Yuanqin He, Jonas Björk, Alexander Riss, Raju Rajesh, Manuela Garnica, Felix Hennersdorf, Jan J. Weigand, Akimitsu Narita, Reinhard Berger, Xinliang Feng, Willi Auwärter, Johannes V. Barth, Carlos-Andres Palma, Klaus Müllen
Format: Article
Language:English
Published: Nature Publishing Group 2017-12-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/s41467-017-01934-1
id doaj-bae30ce09492472a96d838a85983c954
record_format Article
spelling doaj-bae30ce09492472a96d838a85983c9542021-05-11T07:32:55ZengNature Publishing GroupNature Communications2041-17232017-12-01811710.1038/s41467-017-01934-1Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocouplingXiao-Ye Wang0Marcus Richter1Yuanqin He2Jonas Björk3Alexander Riss4Raju Rajesh5Manuela Garnica6Felix Hennersdorf7Jan J. Weigand8Akimitsu Narita9Reinhard Berger10Xinliang Feng11Willi Auwärter12Johannes V. Barth13Carlos-Andres Palma14Klaus Müllen15Max Planck Institute for Polymer Research, Ackermannweg 10Department for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Dresden University of Technology, Mommsenstr. 4Institute for Advanced Study, Technical University of Munich, Lichtenbergstr. 2aDepartment of Physics, Chemistry and Biology, IFM, Linköping UniversityPhysik-Department E20, Technical University of Munich, James-Franck-Str. 1Max Planck Institute for Polymer Research, Ackermannweg 10Physik-Department E20, Technical University of Munich, James-Franck-Str. 1Chair of Inorganic Molecular Chemistry, Dresden University of Technology, Mommsenstr. 4Chair of Inorganic Molecular Chemistry, Dresden University of Technology, Mommsenstr. 4Max Planck Institute for Polymer Research, Ackermannweg 10Department for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Dresden University of Technology, Mommsenstr. 4Department for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Dresden University of Technology, Mommsenstr. 4Physik-Department E20, Technical University of Munich, James-Franck-Str. 1Physik-Department E20, Technical University of Munich, James-Franck-Str. 1Physik-Department E20, Technical University of Munich, James-Franck-Str. 1Max Planck Institute for Polymer Research, Ackermannweg 10Polyaromatic hydrocarbons can be precisely manipulated to yield ever more complex and discrete graphene analogs, such as nanographenes. Here, the authors use azomethine ylide homocoupling to insert an antiaromatic pyrazine ring into the core of a nanographene, and characterize the molecule’s unique electronic character.https://doi.org/10.1038/s41467-017-01934-1
collection DOAJ
language English
format Article
sources DOAJ
author Xiao-Ye Wang
Marcus Richter
Yuanqin He
Jonas Björk
Alexander Riss
Raju Rajesh
Manuela Garnica
Felix Hennersdorf
Jan J. Weigand
Akimitsu Narita
Reinhard Berger
Xinliang Feng
Willi Auwärter
Johannes V. Barth
Carlos-Andres Palma
Klaus Müllen
spellingShingle Xiao-Ye Wang
Marcus Richter
Yuanqin He
Jonas Björk
Alexander Riss
Raju Rajesh
Manuela Garnica
Felix Hennersdorf
Jan J. Weigand
Akimitsu Narita
Reinhard Berger
Xinliang Feng
Willi Auwärter
Johannes V. Barth
Carlos-Andres Palma
Klaus Müllen
Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
Nature Communications
author_facet Xiao-Ye Wang
Marcus Richter
Yuanqin He
Jonas Björk
Alexander Riss
Raju Rajesh
Manuela Garnica
Felix Hennersdorf
Jan J. Weigand
Akimitsu Narita
Reinhard Berger
Xinliang Feng
Willi Auwärter
Johannes V. Barth
Carlos-Andres Palma
Klaus Müllen
author_sort Xiao-Ye Wang
title Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
title_short Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
title_full Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
title_fullStr Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
title_full_unstemmed Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
title_sort exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
publisher Nature Publishing Group
series Nature Communications
issn 2041-1723
publishDate 2017-12-01
description Polyaromatic hydrocarbons can be precisely manipulated to yield ever more complex and discrete graphene analogs, such as nanographenes. Here, the authors use azomethine ylide homocoupling to insert an antiaromatic pyrazine ring into the core of a nanographene, and characterize the molecule’s unique electronic character.
url https://doi.org/10.1038/s41467-017-01934-1
work_keys_str_mv AT xiaoyewang explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT marcusrichter explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT yuanqinhe explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT jonasbjork explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT alexanderriss explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT rajurajesh explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT manuelagarnica explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT felixhennersdorf explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT janjweigand explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT akimitsunarita explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT reinhardberger explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT xinliangfeng explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT williauwarter explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT johannesvbarth explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT carlosandrespalma explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
AT klausmullen explorationofpyrazineembeddedantiaromaticpolycyclichydrocarbonsgeneratedbysolutionandonsurfaceazomethineylidehomocoupling
_version_ 1721452058447446016