Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne

Martin Drohse Kilde; Adrian H. Murray; Cecilie Lindholm Andersen; Freja Eilso Storm; Katrin Schmidt; Anders Kadziola; Kurt V. Mikkelsen; Frank Hampel; Ole Hammerich; Rik R. Tykwinski; Mogens Brondsted Nielsen

doi:10.1038/s41467-019-11700-0

Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne

Martin Drohse Kilde, Adrian H. Murray, Cecilie Lindholm Andersen, Freja Eilso Storm, Katrin Schmidt, Anders Kadziola, Kurt V. Mikkelsen, Frank Hampel, Ole Hammerich, Rik R. Tykwinski, Mogens Brondsted Nielsen

Kemisk Institut

11 Citationer (Scopus)

Abstract

Graphyne allotropes of carbon are fascinating materials, and their electronic properties are predicted to rival those of the “wonder material” graphene. One allotrope of graphyne, having rectangular symmetry rather than hexagonal, stands out as particularly attractive, namely 6,6,12-graphyne. It is currently an insurmountable challenge, however, to design and execute a synthesis of this material. Herein, we present synthesis and electronic properties of molecules that serve as model compounds. These oligomers, so-called radiaannulenes, are prepared by iterative acetylenic coupling reactions. Systematic optical and redox studies indicate the effective conjugation length of the radiaannulene oligomers is nearly met by the length of the trimer. The HOMO-LUMO gap suggested by the series of oligomers is still, however, higher than that expected for 6,6,12-graphyne from theory, which predicts two nonequivalent distorted Dirac cones (no band gap). Thus, the radiaannulene oligomers present a suitable length in one dimension of a sheet, but should be expanded in the second dimension to provide a unique representation of 6,6,12-graphyne.

Originalsprog	Engelsk
Artikelnummer	3714
Tidsskrift	Nature Communications
Vol/bind	10
Antal sider	9
ISSN	2041-1723
DOI	https://doi.org/10.1038/s41467-019-11700-0
Status	Udgivet - 1 dec. 2019

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10.1038/s41467-019-11700-0Licens: CC BY

s41467-019-11700-0Forlagets udgivne version, 0,99 MBLicens: CC BY

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title = "Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne",

abstract = "Graphyne allotropes of carbon are fascinating materials, and their electronic properties are predicted to rival those of the “wonder material” graphene. One allotrope of graphyne, having rectangular symmetry rather than hexagonal, stands out as particularly attractive, namely 6,6,12-graphyne. It is currently an insurmountable challenge, however, to design and execute a synthesis of this material. Herein, we present synthesis and electronic properties of molecules that serve as model compounds. These oligomers, so-called radiaannulenes, are prepared by iterative acetylenic coupling reactions. Systematic optical and redox studies indicate the effective conjugation length of the radiaannulene oligomers is nearly met by the length of the trimer. The HOMO-LUMO gap suggested by the series of oligomers is still, however, higher than that expected for 6,6,12-graphyne from theory, which predicts two nonequivalent distorted Dirac cones (no band gap). Thus, the radiaannulene oligomers present a suitable length in one dimension of a sheet, but should be expanded in the second dimension to provide a unique representation of 6,6,12-graphyne.",

author = "Kilde, {Martin Drohse} and Murray, {Adrian H.} and Andersen, {Cecilie Lindholm} and Storm, {Freja Eilso} and Katrin Schmidt and Anders Kadziola and Mikkelsen, {Kurt V.} and Frank Hampel and Ole Hammerich and Tykwinski, {Rik R.} and Nielsen, {Mogens Brondsted}",

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TY - JOUR

T1 - Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne

AU - Kilde, Martin Drohse

AU - Murray, Adrian H.

AU - Andersen, Cecilie Lindholm

AU - Storm, Freja Eilso

AU - Schmidt, Katrin

AU - Kadziola, Anders

AU - Mikkelsen, Kurt V.

AU - Hampel, Frank

AU - Hammerich, Ole

AU - Tykwinski, Rik R.

AU - Nielsen, Mogens Brondsted

PY - 2019/12/1

Y1 - 2019/12/1

N2 - Graphyne allotropes of carbon are fascinating materials, and their electronic properties are predicted to rival those of the “wonder material” graphene. One allotrope of graphyne, having rectangular symmetry rather than hexagonal, stands out as particularly attractive, namely 6,6,12-graphyne. It is currently an insurmountable challenge, however, to design and execute a synthesis of this material. Herein, we present synthesis and electronic properties of molecules that serve as model compounds. These oligomers, so-called radiaannulenes, are prepared by iterative acetylenic coupling reactions. Systematic optical and redox studies indicate the effective conjugation length of the radiaannulene oligomers is nearly met by the length of the trimer. The HOMO-LUMO gap suggested by the series of oligomers is still, however, higher than that expected for 6,6,12-graphyne from theory, which predicts two nonequivalent distorted Dirac cones (no band gap). Thus, the radiaannulene oligomers present a suitable length in one dimension of a sheet, but should be expanded in the second dimension to provide a unique representation of 6,6,12-graphyne.

AB - Graphyne allotropes of carbon are fascinating materials, and their electronic properties are predicted to rival those of the “wonder material” graphene. One allotrope of graphyne, having rectangular symmetry rather than hexagonal, stands out as particularly attractive, namely 6,6,12-graphyne. It is currently an insurmountable challenge, however, to design and execute a synthesis of this material. Herein, we present synthesis and electronic properties of molecules that serve as model compounds. These oligomers, so-called radiaannulenes, are prepared by iterative acetylenic coupling reactions. Systematic optical and redox studies indicate the effective conjugation length of the radiaannulene oligomers is nearly met by the length of the trimer. The HOMO-LUMO gap suggested by the series of oligomers is still, however, higher than that expected for 6,6,12-graphyne from theory, which predicts two nonequivalent distorted Dirac cones (no band gap). Thus, the radiaannulene oligomers present a suitable length in one dimension of a sheet, but should be expanded in the second dimension to provide a unique representation of 6,6,12-graphyne.

U2 - 10.1038/s41467-019-11700-0

DO - 10.1038/s41467-019-11700-0

M3 - Journal article

C2 - 31420550

SN - 2041-1723

VL - 10

JO - Nature Communications

JF - Nature Communications

M1 - 3714

ER -

Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne

Abstract

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