Self-assembly directed one-step synthesis of [4]radialene on Cu(100) surfaces

Li, Qing; Gao, Jianzhi; Li, Youyong; Fuentes-Cabrera, Miguel; Liu, Mengxi; Qiu, Xiaohui; Lin, Haiping; Chi, Lifeng; Pan, Minghu

doi:10.1038/s41467-018-05472-2

Title: Self-assembly directed one-step synthesis of [4]radialene on Cu(100) surfaces

Journal Article · 05 August 2018 · Nature Communications

DOI: https://doi.org/10.1038/s41467-018-05472-2 · OSTI ID:1463979

Li, Qing ^[1]; Gao, Jianzhi ^[2];

^[1]; Fuentes-Cabrera, Miguel ^[3]; Liu, Mengxi ^[4]; Qiu, Xiaohui ^[5];

^[1]; Chi, Lifeng ^[1]; Pan, Minghu ^[6]

Soochow Univ., Suzhou (China). Inst. of Functional Nano & Soft Materials (FUNSOM). Jiangsu Key Lab. for Carbon-Based Functional Materials & Devices
Shaanxi Normal Univ., Xi’an (China). School of Physics and Information Technology
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences. Computational Sciences and Engineering Division
National Center for Nanoscience and Technology, Beijing (China). CAS Key Lab. of Standardization and Measurement for Nanotechnology. CAS Center for Excellence in Nanoscience
National Center for Nanoscience and Technology, Beijing (China). CAS Key Lab. of Standardization and Measurement for Nanotechnology. CAS Center for Excellence in Nanoscience; Univ. of Chinese Academy of Sciences, Beijing (China)
Huazhong Univ. of Science and Technology, Wuhan (China). School of Physics

The synthetic challenges of radialenes have precluded their practical applications. Here, we report a one-step synthetic protocol of [4]radialene on a copper surface. High-resolution scanning tunneling microscopy measurements reveal that such catalytic reaction proceeds readily with high selectivity at the temperature below 120 K. First-principles calculations show that the reaction pathway is characterized by firstly the cooperative inter-molecular hydrogen tautomerization and then the C–C bond formation. The feasibility of such cyclotetramerization reaction can be interpreted by the surface effect of Cu(100), which firstly plays an important role in directing the molecular assembly and then serves as an active catalyst in the hydrogen tautomerization and C–C coupling processes. This work presents not only a novel strategy to the scant number of synthetic methods to produce [4]radialenes via a novel [1 + 1 + 1 + 1] reaction pathway, but also a successful example of C–C bond coupling reactions guided by the surface-induced C–H/π assembly.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Soochow Univ., Suzhou (China); National Center for Nanoscience and Technology, Beijing (China)

Sponsoring Organization:: USDOE Office of Science (SC); National Natural Science Foundation of China (NSFC); Natural Science Foundation of Jiangsu Province (China); Major State Basic Research Development Program of China

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1463979

Journal Information:: Nature Communications, Journal Name: Nature Communications Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (88)

Tunneling Spectroscopy and Inverse Photoemission: Image and Field States Binnig, G.; Frank, K. H.; Fuchs, H. Physical Review Letters, Vol. 55, Issue 9 https://doi.org/10.1103/PhysRevLett.55.991	journal	August 1985
On-Surface Synthesis of Rylene-Type Graphene Nanoribbons Zhang, Haiming; Lin, Haiping; Sun, Kewei Journal of the American Chemical Society, Vol. 137, Issue 12 https://doi.org/10.1021/ja511995r	journal	March 2015
Bottom-Up Synthesis of Metalated Carbyne Sun, Qiang; Cai, Liangliang; Wang, Shiyong Journal of the American Chemical Society, Vol. 138, Issue 4 https://doi.org/10.1021/jacs.5b10725	journal	January 2016
The Chemistry of Photodimers of Maleic and Fumaric Acid Derivatives. IV. ¹ Tetramethylenecyclobutane Griffin, Gary W.; Peterson, Laurence I. Journal of the American Chemical Society, Vol. 84, Issue 17 https://doi.org/10.1021/ja00876a033	journal	September 1962
Surface-assisted Dehydrogenative Homocoupling of Porphine Molecules Wiengarten, Alissa; Seufert, Knud; Auwärter, Willi Journal of the American Chemical Society, Vol. 136, Issue 26 https://doi.org/10.1021/ja501680n	journal	June 2014
Bottom-Up Synthesis of Metalated Carbyne Sun, Qiang; Cai, Liangliang; Wang, Shiyong Journal of the American Chemical Society, Vol. 138, Issue 4 https://doi.org/10.1021/jacs.5b10725	journal	January 2016
Thermal and Photochemical Isomerization of Tetraaryl Tetrakis(trifluoromethyl)[4]radialenes Uno, Hidemitsu; Kasahara, Ken-ichi; Nibu, Nobumasa The Journal of Organic Chemistry, Vol. 65, Issue 6 https://doi.org/10.1021/jo990699v	journal	March 2000
Two-Dimensional Polymer Formation on Surfaces: Insight into the Roles of Precursor Mobility and Reactivity Bieri, Marco; Nguyen, Manh-Thuong; Gröning, Oliver Journal of the American Chemical Society, Vol. 132, Issue 46 https://doi.org/10.1021/ja107947z	journal	November 2010
Linear Alkane Polymerization on a Gold Surface Zhong, D.; Franke, J. -H.; Podiyanachari, S. K. Science, Vol. 334, Issue 6053 https://doi.org/10.1126/science.1211836	journal	October 2011
Special points for Brillouin-zone integrations Monkhorst, Hendrik J.; Pack, James D. Physical Review B, Vol. 13, Issue 12, p. 5188-5192 https://doi.org/10.1103/PhysRevB.13.5188	journal	June 1976
Steering On-Surface Polymerization with Metal-Directed Template Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne Journal of the American Chemical Society, Vol. 135, Issue 9 https://doi.org/10.1021/ja311890n	journal	February 2013
The Chemical Structure of a Molecule Resolved by Atomic Force Microscopy Gross, L.; Mohn, F.; Moll, N. Science, Vol. 325, Issue 5944 https://doi.org/10.1126/science.1176210	journal	August 2009
Oligomeric and Polymeric Systems with a Cross-Conjugated π-Framework Gholami, Mojtaba; Tykwinski, Rik R. ChemInform, Vol. 38, Issue 18 https://doi.org/10.1002/chin.200718250	journal	May 2007
Linear Alkane Polymerization on a Gold Surface Zhong, D.; Franke, J. -H.; Podiyanachari, S. K. Science, Vol. 334, Issue 6053 https://doi.org/10.1126/science.1211836	journal	October 2011
Theories of scanning probe microscopes at the atomic scale Hofer, Werner A.; Foster, Adam S.; Shluger, Alexander L. Reviews of Modern Physics, Vol. 75, Issue 4 https://doi.org/10.1103/RevModPhys.75.1287	journal	October 2003
Transforming Surface Coordination Polymers into Covalent Surface Polymers: Linked Polycondensed Aromatics through Oligomerization of N-Heterocyclic Carbene Intermediates Matena, Manfred; Riehm, Till; Stöhr, Meike Angewandte Chemie, Vol. 120, Issue 13 https://doi.org/10.1002/ange.200704072	journal	March 2008
Transforming Surface Coordination Polymers into Covalent Surface Polymers: Linked Polycondensed Aromatics through Oligomerization of N-Heterocyclic Carbene Intermediates Matena, Manfred; Riehm, Till; Stöhr, Meike Angewandte Chemie International Edition, Vol. 47, Issue 13 https://doi.org/10.1002/anie.200704072	journal	March 2008
Real-Space Identification of Intermolecular Bonding with Atomic Force Microscopy Zhang, J.; Chen, P.; Yuan, B. Science, Vol. 342, Issue 6158 https://doi.org/10.1126/science.1242603	journal	September 2013
On-Surface Covalent Coupling in Ultrahigh Vacuum Gourdon, André Angewandte Chemie International Edition, Vol. 47, Issue 37 https://doi.org/10.1002/anie.200802229	journal	September 2008
Generation, manipulation and characterization of molecules by atomic force microscopy Pavliček, Niko; Gross, Leo Nature Reviews Chemistry, Vol. 1, Issue 1 https://doi.org/10.1038/s41570-016-0005	journal	January 2017
Surface-Controlled Mono/Diselective ortho C–H Bond Activation Li, Qing; Yang, Biao; Lin, Haiping Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b13286	journal	February 2016
Preparation and Properties, Reactions, and Applications of Radialenes Hopf, Henning; Maas, Gerhard Angewandte Chemie International Edition in English, Vol. 31, Issue 8 https://doi.org/10.1002/anie.199209313	journal	August 1992
Thermal and Photochemical Isomerization of Tetraaryl Tetrakis(trifluoromethyl)[4]radialenes Uno, Hidemitsu; Kasahara, Ken-ichi; Nibu, Nobumasa The Journal of Organic Chemistry, Vol. 65, Issue 6 https://doi.org/10.1021/jo990699v	journal	March 2000
Atomically precise bottom-up fabrication of graphene nanoribbons Cai, J. M.; Ruffieux, P.; Jaafar, R. Nature Publishing Group https://doi.org/10.5167/uzh-36020	text	January 2010
Nickel-catalyzed cyclodimerization of [5]cumulene (hexapentaene). Synthesis of a novel [4]radialene system Iyoda, Masahiko; Kuwatani, Yoshiyuki; Oda, Masaji Journal of the American Chemical Society, Vol. 111, Issue 10 https://doi.org/10.1021/ja00192a051	journal	May 1989
Nano-architectures by covalent assembly of molecular building blocks Grill, Leonhard; Dyer, Matthew; Lafferentz, Leif Nature Nanotechnology, Vol. 2, Issue 11 https://doi.org/10.1038/nnano.2007.346	journal	October 2007
Glaser Coupling at Metal Surfaces Gao, Hong-Ying; Wagner, Hendrik; Zhong, Dingyong Angewandte Chemie International Edition, Vol. 52, Issue 14 https://doi.org/10.1002/anie.201208597	journal	February 2013
Direct Visualization of Surface-Assisted Two-Dimensional Diyne Polycyclotrimerization Zhou, Haitao; Liu, Jianzhao; Du, Shixuan Journal of the American Chemical Society, Vol. 136, Issue 15 https://doi.org/10.1021/ja501308s	journal	April 2014
Catalytic Dealkylation of Ethers to Alcohols on Metal Surfaces Yang, Biao; Lin, Haiping; Miao, Kangjian Angewandte Chemie, Vol. 128, Issue 34 https://doi.org/10.1002/ange.201602414	journal	July 2016
Nickel-catalyzed cyclodimerization of [5]cumulene (hexapentaene). Synthesis of a novel [4]radialene system Iyoda, Masahiko; Kuwatani, Yoshiyuki; Oda, Masaji Journal of the American Chemical Society, Vol. 111, Issue 10 https://doi.org/10.1021/ja00192a051	journal	May 1989
Two-Dimensional Chirality Transfer via On-Surface Reaction Zhang, Haiming; Gong, Zhongmiao; Sun, Kewei Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b05597	journal	September 2016
Surface-assisted Dehydrogenative Homocoupling of Porphine Molecules Wiengarten, Alissa; Seufert, Knud; Auwärter, Willi Journal of the American Chemical Society, Vol. 136, Issue 26 https://doi.org/10.1021/ja501680n	journal	June 2014
Bottom-Up Synthesis of Metalated Carbyne Ju, Huanxin; Cai, Liangliang; Fasel, Roman American Chemical Society https://doi.org/10.7892/boris.90506	text	January 2016
Synthesis and Structure of a Diphospha[4]radialene Toyota, Kozo; Tashiro, Katsuya; Yoshifuji, Masaaki Angewandte Chemie International Edition in English, Vol. 32, Issue 8 https://doi.org/10.1002/anie.199311631	journal	August 1993
On-Surface Synthesis of Carbon-Based Scaffolds and Nanomaterials Using Terminal Alkynes Klappenberger, Florian; Zhang, Yi-Qi; Björk, Jonas Accounts of Chemical Research, Vol. 48, Issue 7 https://doi.org/10.1021/acs.accounts.5b00174	journal	June 2015
Surface-Assisted Organic Synthesis of Hyperbenzene Nanotroughs Fan, Qitang; Wang, Cici; Han, Yong Angewandte Chemie International Edition, Vol. 52, Issue 17 https://doi.org/10.1002/anie.201300610	journal	March 2013
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Surface-assisted cyclodehydrogenation provides a synthetic route towards easily processable and chemically tailored nanographenes Treier, Matthias; Pignedoli, Carlo Antonio; Laino, Teodoro Nature Chemistry, Vol. 3, Issue 1 https://doi.org/10.1038/nchem.891	journal	November 2010
Tunneling Spectroscopy and Inverse Photoemission: Image and Field States Binnig, G.; Frank, K. H.; Fuchs, H. Physical Review Letters, Vol. 55, Issue 9 https://doi.org/10.1103/physrevlett.55.991	journal	August 1985
Modern techniques of surface science Grovenor, C. R. M. Materials Characterization, Vol. 34, Issue 3 https://doi.org/10.1016/1044-5803(94)00096-4	journal	April 1995
Two-Dimensional Polymer Formation on Surfaces: Insight into the Roles of Precursor Mobility and Reactivity Bieri, Marco; Nguyen, Manh-Thuong; Gröning, Oliver Journal of the American Chemical Society, Vol. 132, Issue 46 https://doi.org/10.1021/ja107947z	journal	November 2010
CHEMISTRY: Extending Polymer Conjugation into the Second Dimension Perepichka, D. F.; Rosei, F. Science, Vol. 323, Issue 5911 https://doi.org/10.1126/science.1165429	journal	January 2009
Local Spectroscopy of Image-Potential-Derived States: From Single Molecules to Monolayers of Benzene on Cu(111) Dougherty, D. B.; Maksymovych, P.; Lee, J. Physical Review Letters, Vol. 97, Issue 23 https://doi.org/10.1103/PhysRevLett.97.236806	journal	December 2006
Structural Variation in Surface-Supported Synthesis by Adjusting the Stoichiometric Ratio of the Reactants Gong, Zhongmiao; Yang, Biao; Lin, Haiping ACS Nano, Vol. 10, Issue 4 https://doi.org/10.1021/acsnano.5b07601	journal	April 2016
On-Surface Covalent Coupling in Ultrahigh Vacuum Gourdon, André Angewandte Chemie International Edition, Vol. 47, Issue 37 https://doi.org/10.1002/anie.200802229	journal	September 2008
Structural Variation in Surface-Supported Synthesis by Adjusting the Stoichiometric Ratio of the Reactants Gong, Zhongmiao; Yang, Biao; Lin, Haiping ACS Nano, Vol. 10, Issue 4 https://doi.org/10.1021/acsnano.5b07601	journal	April 2016
Unique intermolecular reaction of simple porphyrins at a metal surface gives covalent nanostructures In’t Veld, Mendel; Iavicoli, Patrizia; Haq, Sam Chemical Communications, Issue 13 https://doi.org/10.1039/b718865j	journal	January 2008
The adsorption of xenon by W(111), and its interaction with preadsorbed oxygen Dresser, Miles J.; Madey, Theodore E.; Yates, John T. Surface Science, Vol. 42, Issue 2 https://doi.org/10.1016/0039-6028(74)90037-5	journal	April 1974
Generation, manipulation and characterization of molecules by atomic force microscopy Pavliček, Niko; Gross, Leo Nature Reviews Chemistry, Vol. 1, Issue 1 https://doi.org/10.1038/s41570-016-0005	journal	January 2017
Surface-Assisted Organic Synthesis of Hyperbenzene Nanotroughs Fan, Qitang; Wang, Cici; Han, Yong Angewandte Chemie International Edition, Vol. 52, Issue 17 https://doi.org/10.1002/anie.201300610	journal	March 2013
Atomically precise bottom-up fabrication of graphene nanoribbons Cai, Jinming; Ruffieux, Pascal; Jaafar, Rached Nature, Vol. 466, Issue 7305 https://doi.org/10.1038/nature09211	journal	July 2010
Supramolecular Self-Assembly of π-Conjugated Hydrocarbons via 2D Cooperative CH/π Interaction Li, Qing; Han, Chengbo; Horton, Scott R. ACS Nano, Vol. 6, Issue 1 https://doi.org/10.1021/nn203952e	journal	December 2011
Two-Dimensional Chirality Transfer via On-Surface Reaction Zhang, Haiming; Gong, Zhongmiao; Sun, Kewei Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b05597	journal	September 2016
Atomically precise bottom-up fabrication of graphene nanoribbons Cai, J. M.; Ruffieux, P.; Jaafar, R. Nature Publishing Group https://doi.org/10.5167/uzh-36020	text	January 2010
Oligomeric and Polymeric Systems with a Cross-conjugated π-Framework ^† Gholami, Mojtaba; Tykwinski, Rik R. Chemical Reviews, Vol. 106, Issue 12 https://doi.org/10.1021/cr0505573	journal	December 2006
On-Surface Synthesis of Carbon-Based Scaffolds and Nanomaterials Using Terminal Alkynes Klappenberger, Florian; Zhang, Yi-Qi; Björk, Jonas Accounts of Chemical Research, Vol. 48, Issue 7 https://doi.org/10.1021/acs.accounts.5b00174	journal	June 2015
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/physrevlett.77.3865	journal	October 1996
On-Surface Synthesis of Single-Layered Two-Dimensional Covalent Organic Frameworks via Solid–Vapor Interface Reactions Liu, Xuan-He; Guan, Cui-Zhong; Ding, San-Yuan Journal of the American Chemical Society, Vol. 135, Issue 28 https://doi.org/10.1021/ja403464h	journal	May 2013
Direct Visualization of Surface-Assisted Two-Dimensional Diyne Polycyclotrimerization Zhou, Haitao; Liu, Jianzhao; Du, Shixuan Journal of the American Chemical Society, Vol. 136, Issue 15 https://doi.org/10.1021/ja501308s	journal	April 2014
On-Surface Synthesis of Single-Layered Two-Dimensional Covalent Organic Frameworks via Solid–Vapor Interface Reactions Liu, Xuan-He; Guan, Cui-Zhong; Ding, San-Yuan Journal of the American Chemical Society, Vol. 135, Issue 28 https://doi.org/10.1021/ja403464h	journal	May 2013
Preparation and Properties, Reactions, and Applications of Radialenes Hopf, Henning; Maas, Gerhard Angewandte Chemie International Edition in English, Vol. 31, Issue 8 https://doi.org/10.1002/anie.199209313	journal	August 1992
Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons Narita, Akimitsu; Feng, Xinliang; Hernandez, Yenny Nature Chemistry, Vol. 6, Issue 2 https://doi.org/10.1038/nchem.1819	journal	December 2013
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
The adsorption of xenon by W(111), and its interaction with preadsorbed oxygen Dresser, Miles J.; Madey, Theodore E.; Yates, John T. Surface Science, Vol. 42, Issue 2 https://doi.org/10.1016/0039-6028(74)90037-5	journal	April 1974
Catalytic Dealkylation of Ethers to Alcohols on Metal Surfaces Yang, Biao; Lin, Haiping; Miao, Kangjian Angewandte Chemie, Vol. 128, Issue 34 https://doi.org/10.1002/ange.201602414	journal	July 2016
Van der Waals density functionals applied to solids Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos arXiv https://doi.org/10.48550/arxiv.1102.1358	text	January 2011
The Chemistry of Photodimers of Maleic and Fumaric Acid Derivatives. IV. ¹ Tetramethylenecyclobutane Griffin, Gary W.; Peterson, Laurence I. Journal of the American Chemical Society, Vol. 84, Issue 17 https://doi.org/10.1021/ja00876a033	journal	September 1962
The Chemical Structure of a Molecule Resolved by Atomic Force Microscopy Gross, L.; Mohn, F.; Moll, N. Science, Vol. 325, Issue 5944 https://doi.org/10.1126/science.1176210	journal	August 2009
On-Surface Azide–Alkyne Cycloaddition on Cu(111): Does It “Click” in Ultrahigh Vacuum? Bebensee, Fabian; Bombis, Christian; Vadapoo, Sundar-Raja Journal of the American Chemical Society, Vol. 135, Issue 6 https://doi.org/10.1021/ja312303a	journal	January 2013
Supramolecular Self-Assembly of π-Conjugated Hydrocarbons via 2D Cooperative CH/π Interaction Li, Qing; Han, Chengbo; Horton, Scott R. ACS Nano, Vol. 6, Issue 1 https://doi.org/10.1021/nn203952e	journal	December 2011
Surface-Controlled Mono/Diselective ortho C–H Bond Activation Li, Qing; Yang, Biao; Lin, Haiping Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b13286	journal	February 2016
Electronic Control over Attachment and Self-Assembly of Alkyne Groups on Gold Li, Qing; Han, Chengbo; Fuentes-Cabrera, Miguel ACS Nano, Vol. 6, Issue 10 https://doi.org/10.1021/nn303734r	journal	September 2012
Reducing Dzyaloshinskii-Moriya interaction and field-free spin-orbit torque switching in synthetic antiferromagnets Chen, Ruyi; Cui, Qirui; Liao, Liyang Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-23414-3	journal	May 2021
Self-Organized and Cu-Coordinated Surface Linear Polymerization Li, Qing; Owens, Jonathan R.; Han, Chengbo Scientific Reports, Vol. 3, Issue 1 https://doi.org/10.1038/srep02102	journal	July 2013
Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22 https://doi.org/10.1063/1.1323224	journal	December 2000
Glaser Coupling at Metal Surfaces Gao, Hong-Ying; Wagner, Hendrik; Zhong, Dingyong Angewandte Chemie International Edition, Vol. 52, Issue 14 https://doi.org/10.1002/anie.201208597	journal	February 2013
On-surface aryl–aryl coupling via selective C–H activation Sun, Qiang; Zhang, Chi; Kong, Huihui Chem. Commun., Vol. 50, Issue 80 https://doi.org/10.1039/C4CC05482B	journal	January 2014
Steering On-Surface Polymerization with Metal-Directed Template Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne Journal of the American Chemical Society, Vol. 135, Issue 9 https://doi.org/10.1021/ja311890n	journal	February 2013
Organized Formation of 2D Extended Covalent Organic Frameworks at Surfaces Zwaneveld, Nikolas A. A.; Pawlak, Rémy; Abel, Mathieu Journal of the American Chemical Society, Vol. 130, Issue 21 https://doi.org/10.1021/ja800906f	journal	May 2008
Van der Waals density functionals applied to solids Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Physical Review B, Vol. 83, Issue 19 https://doi.org/10.1103/PhysRevB.83.195131	journal	May 2011
Organized Formation of 2D Extended Covalent Organic Frameworks at Surfaces Zwaneveld, Nikolas A. A.; Pawlak, Rémy; Abel, Mathieu Journal of the American Chemical Society, Vol. 130, Issue 21 https://doi.org/10.1021/ja800906f	journal	May 2008
CHEMISTRY: Extending Polymer Conjugation into the Second Dimension Perepichka, D. F.; Rosei, F. Science, Vol. 323, Issue 5911 https://doi.org/10.1126/science.1165429	journal	January 2009
Homo-coupling of terminal alkynes on a noble metal surface Zhang, Yi-Qi; Kepčija, Nenad; Kleinschrodt, Martin Nature Communications, Vol. 3, Issue 1, Article No. 1286 (2012) https://doi.org/10.1038/ncomms2291	journal	January 2012
Synthesis of Surface Covalent Organic Frameworks via Dimerization and Cyclotrimerization of Acetyls Yang, Biao; Björk, Jonas; Lin, Haiping Journal of the American Chemical Society, Vol. 137, Issue 15 https://doi.org/10.1021/jacs.5b00774	journal	March 2015
Homo-coupling of terminal alkynes on a noble metal surface Zhang, Yi-Qi; Kepčija, Nenad; Kleinschrodt, Martin Nature Communications, Vol. 3, Issue 1, Article No. 1286 (2012) https://doi.org/10.1038/ncomms2291	journal	January 2012
On-Surface Azide–Alkyne Cycloaddition on Cu(111): Does It “Click” in Ultrahigh Vacuum? Bebensee, Fabian; Bombis, Christian; Vadapoo, Sundar-Raja Journal of the American Chemical Society, Vol. 135, Issue 6 https://doi.org/10.1021/ja312303a	journal	January 2013
Catalytic Dealkylation of Ethers to Alcohols on Metal Surfaces Yang, Biao; Lin, Haiping; Miao, Kangjian Angewandte Chemie International Edition, Vol. 55, Issue 34 https://doi.org/10.1002/anie.201602414	journal	July 2016

Cited By (12)

On‐Surface Evolution of meso ‐Isomerism in Two‐Dimensional Supramolecular Assemblies Park, Juyeon; Kim, Ju‐Hyung; Bak, Sunmi Angewandte Chemie International Edition, Vol. 58, Issue 28 https://doi.org/10.1002/anie.201904290	journal	July 2019
Identifying Multinuclear Organometallic Intermediates in On‐Surface [2+2] Cycloaddition Reactions Zhang, Ran; Xia, Bowen; Xu, Hu Angewandte Chemie International Edition, Vol. 58, Issue 46 https://doi.org/10.1002/anie.201909278	journal	November 2019
Highly emissive phenylene-expanded [5]radialene Yu, Jie; Tang, Chunlin; Gu, Xinggui Chemical Communications, Vol. 56, Issue 27 https://doi.org/10.1039/d0cc00122h	journal	January 2020
Reaction selectivity of homochiral versus heterochiral intermolecular reactions of prochiral terminal alkynes on surfaces Wang, Tao; Lv, Haifeng; Huang, Jianmin Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-12102-y	journal	September 2019
Reaction selectivity of homochiral versus heterochiral intermolecular reactions of prochiral terminal alkynes on surfaces Wang, Tao; Lv, Haifeng; Huang, Jianmin Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-12102-y	journal	September 2019
Atomic‐Scale Visualization of the Stepwise Metal‐Mediated Dehalogenative Cycloaddition Reaction Pathways: Competition between Radicals and Organometallic Intermediates Zhang, Chi; Kazuma, Emiko; Kim, Yousoo Angewandte Chemie, Vol. 131, Issue 49 https://doi.org/10.1002/ange.201909111	journal	October 2019
Identifying Multinuclear Organometallic Intermediates in On‐Surface [2+2] Cycloaddition Reactions Zhang, Ran; Xia, Bowen; Xu, Hu Angewandte Chemie, Vol. 131, Issue 46 https://doi.org/10.1002/ange.201909278	journal	October 2019
Controlling a Chemical Coupling Reaction on a Surface: Tools and Strategies for On-Surface Synthesis Clair, Sylvain; de Oteyza, Dimas G. Chemical Reviews, Vol. 119, Issue 7 https://doi.org/10.1021/acs.chemrev.8b00601	journal	March 2019
On‐Surface Evolution of meso ‐Isomerism in Two‐Dimensional Supramolecular Assemblies Park, Juyeon; Kim, Ju‐Hyung; Bak, Sunmi Angewandte Chemie, Vol. 131, Issue 28 https://doi.org/10.1002/ange.201904290	journal	June 2019
Two‐Sidedness of Surface Reaction Mediation Chen, Haoran; Zhu, Hao; Huang, Zhichao Advanced Materials, Vol. 31, Issue 50 https://doi.org/10.1002/adma.201902080	journal	July 2019
Atomic‐Scale Visualization of the Stepwise Metal‐Mediated Dehalogenative Cycloaddition Reaction Pathways: Competition between Radicals and Organometallic Intermediates Zhang, Chi; Kazuma, Emiko; Kim, Yousoo Angewandte Chemie International Edition, Vol. 58, Issue 49 https://doi.org/10.1002/anie.201909111	journal	December 2019
Two-Dimensional Hydrogen-Bonded Nanoarchitecture Composed of Rectangular 3,4,9,10-Perylenetetracarboxylic Diimide and Boomerang-Shaped Molecules Resulting from the Dissociation of 1,3,5-Tris(4-aminophenyl)benzene Hieulle, Jeremy; Silly, Fabien ACS Omega, Vol. 5, Issue 8 https://doi.org/10.1021/acsomega.9b03453	journal	February 2020

Similar Records

High-Resolution Infrared and Electron-Diffraction Studies of Trimethylenecyclopropane ([3]-Radialene)

Journal Article · 2013 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory · OSTI ID:1088634

Wright, Corey; Holmes, Joshua; Nibler, Joseph W.; +5 more

A Theoretical Investigation of the Structure and Reactivity of the Molecular Constituents of Oil Sand and Oil Shale

Technical Report · 2016 · OSTI ID:1333568

Parish, Carol A.

Linear pi-Acceptor-Templated Dynamic Clipping to Macrobicycles and[2]Rotaxanes

Journal Article · 2009 · Angewandte Chemie International Edition · OSTI ID:965776

Klivansky, Liana M; Koshkakaryan, Gayane; Cao, Dennis; +1 more

Related Subjects

36 MATERIALS SCIENCE
density functional theory
scanning probe microscopy
surface assembly

Title: Self-assembly directed one-step synthesis of [4]radialene on Cu(100) surfaces

Citation Formats

References (88)

Cited By (12)

Similar Records

Related Subjects