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Synthesis and Characterization of π-Extended Triangulene

Cite this: J. Am. Chem. Soc. 2019, 141, 27, 10621–10625
Publication Date (Web):June 26, 2019
https://doi.org/10.1021/jacs.9b05319
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    Abstract

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    The electronic and magnetic properties of nanographenes strongly depend on their size, shape and topology. While many nanographenes present a closed-shell electronic structure, certain molecular topologies may lead to an open-shell structure. Triangular-shaped nanographenes with zigzag edges, which exist as neutral radicals, are of considerable interest both in fundamental science and for future technologies aimed at harnessing their intrinsic high-spin magnetic ground states for spin-based operations and information storage. Their synthesis, however, is extremely challenging owing to the presence of unpaired electrons, which confers them with enhanced reactivity. We report a combined in-solution and on-surface synthesis of π-extended triangulene, a non-Kekulé nanographene with the structural formula C33H15, consisting of ten benzene rings fused in a triangular fashion. The distinctive topology of the molecule entails the presence of three unpaired electrons that couple to form a spin quartet ground state. The structure of individual molecules adsorbed on an inert gold surface is confirmed through ultrahigh-resolution scanning tunneling microscopy. The electronic properties are studied via scanning tunneling spectroscopy, wherein unambiguous spectroscopic signatures of the spin-split singly occupied molecular orbitals are found. Detailed insight into its properties is obtained through tight-binding, density functional and many-body perturbation theory calculations, with the latter providing evidence that π-extended triangulene retains its open-shell quartet ground state on the surface. Our work provides unprecedented access to open-shell nanographenes with high-spin ground states, potentially useful in carbon-based spintronics.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b05319.

    • Detailed synthetic description of chemical compounds reported in this study (Schemes S1–S4) and associated solution characterization data (Figures S5–S15), additional STM and STS data (Figures S1–S3), additional calculations (Figure S4) and experimental and calculation methods (PDF)

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    46. Prince Ravat, Olivier Blacque, Michal Juríček. Benzo[cd]triangulene: A Spin 1/2 Graphene Fragment. The Journal of Organic Chemistry 2020, 85 (1) , 92-100. https://doi.org/10.1021/acs.joc.9b02163
    47. Iago Pozo, Zsolt Majzik, Niko Pavliček, Manuel Melle-Franco, Enrique Guitián, Diego Peña, Leo Gross, Dolores Pérez. Revisiting Kekulene: Synthesis and Single-Molecule Imaging. Journal of the American Chemical Society 2019, 141 (39) , 15488-15493. https://doi.org/10.1021/jacs.9b07926
    48. Peter Ribar, Tomáš Šolomek, Michal Juríček. Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar’s Hydrocarbon Triangulene. Organic Letters 2019, 21 (17) , 7124-7128. https://doi.org/10.1021/acs.orglett.9b02683
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    51. Bo Chen, Lin Xue, Yan Han, Zhi Yang, Yong-Jia Zhang. Magnetic semiconducting borophenes and their derivatives. Physical Chemistry Chemical Physics 2023, 25 (45) , 30897-30902. https://doi.org/10.1039/D3CP04069K
    52. Manuel Vilas‐Varela, Francisco Romero‐Lara, Alessio Vegliante, Jan Patrick Calupitan, Adrián Martínez, Lorenz Meyer, Unai Uriarte‐Amiano, Niklas Friedrich, Dongfei Wang, Fabian Schulz, Natalia E. Koval, María E. Sandoval‐Salinas, David Casanova, Martina Corso, Emilio Artacho, Diego Peña, José Ignacio Pascual. On‐Surface Synthesis and Characterization of a High‐Spin Aza‐[5]‐Triangulene. Angewandte Chemie 2023, 135 (41) https://doi.org/10.1002/ange.202307884
    53. Manuel Vilas‐Varela, Francisco Romero‐Lara, Alessio Vegliante, Jan Patrick Calupitan, Adrián Martínez, Lorenz Meyer, Unai Uriarte‐Amiano, Niklas Friedrich, Dongfei Wang, Fabian Schulz, Natalia E. Koval, María E. Sandoval‐Salinas, David Casanova, Martina Corso, Emilio Artacho, Diego Peña, José Ignacio Pascual. On‐Surface Synthesis and Characterization of a High‐Spin Aza‐[5]‐Triangulene. Angewandte Chemie International Edition 2023, 62 (41) https://doi.org/10.1002/anie.202307884
    54. J. C. G. Henriques, J. Fernández-Rossier. Anatomy of linear and nonlinear intermolecular exchange in S = 1 nanographene. Physical Review B 2023, 108 (15) https://doi.org/10.1103/PhysRevB.108.155423
    55. A. A. Starikova, M. G. Chegerev, A. G. Starikov. Phenalenyl-Substituted Stilbenes as the Basis for Spin Switches: Quantum-Chemical Modeling. Russian Journal of General Chemistry 2023, 93 (10) , 2534-2541. https://doi.org/10.1134/S1070363223100080
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    58. L. Fiorini Filho, C.J. Terroso, F.A.L. de Souza, W.S. Paz, F.N.N. Pansini. Spin state engineering of triangulene graphene embedded in h-BN nanoflake. Carbon 2023, 213 , 118186. https://doi.org/10.1016/j.carbon.2023.118186
    59. Hazem Abdelsalam, Qinfang Zhang. Spintronic properties of 2D heterostructures from laterally connected graphene and hBN quantum dots. Chemical Physics Letters 2023, 825 , 140591. https://doi.org/10.1016/j.cplett.2023.140591
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    64. Ziying Li, Shuilin Li, Yongjie Xu, Nujiang Tang. Recent advances in magnetism of graphene from 0D to 2D. Chemical Communications 2023, 59 (42) , 6286-6300. https://doi.org/10.1039/D3CC01311A
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    69. António J. C. Varandas. Can the quasi‐molecule concept help in deciphering planarity? The case of polycyclic aromatic hydrocarbons. International Journal of Quantum Chemistry 2023, 123 (4) https://doi.org/10.1002/qua.27036
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    71. Hui Zhang, Jianchen Lu, Yong Zhang, Lei Gao, Xin-Jing Zhao, Yuan-Zhi Tan, Jinming Cai. Magnetism engineering of nanographene: An enrichment strategy by co-depositing diverse precursors on Au(111). Chinese Chemical Letters 2023, 34 (1) , 107450. https://doi.org/10.1016/j.cclet.2022.04.048
    72. R Ortiz, G Catarina, J Fernández-Rossier. Theory of triangulene two-dimensional crystals. 2D Materials 2023, 10 (1) , 015015. https://doi.org/10.1088/2053-1583/aca4e2
    73. Shiyong Wang, Tomohiko Nishiuchi, Carlo A. Pignedoli, Xuelin Yao, Marco Di Giovannantonio, Yan Zhao, Akimitsu Narita, Xinliang Feng, Klaus Müllen, Pascal Ruffieux, Roman Fasel. Steering on-surface reactions through molecular steric hindrance and molecule-substrate van der Waals interactions. Quantum Frontiers 2022, 1 (1) https://doi.org/10.1007/s44214-022-00023-9
    74. Suqin Cheng, Zhijie Xue, Can Li, Yufeng Liu, Longjun Xiang, Youqi Ke, Kaking Yan, Shiyong Wang, Ping Yu. On-surface synthesis of triangulene trimers via dehydration reaction. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-29371-9
    75. Cheng Chen, Jiayi Lu, Yang Lv, Yuyi Yan, Qiang Sun, Akimitsu Narita, Klaus Müllen, Xiao‐Ye Wang. Heteroatom‐Edged [4]Triangulene: Facile Synthesis and Two‐Dimensional On‐Surface Self‐Assemblies**. Angewandte Chemie 2022, 134 (47) https://doi.org/10.1002/ange.202212594
    76. Cheng Chen, Jiayi Lu, Yang Lv, Yuyi Yan, Qiang Sun, Akimitsu Narita, Klaus Müllen, Xiao‐Ye Wang. Heteroatom‐Edged [4]Triangulene: Facile Synthesis and Two‐Dimensional On‐Surface Self‐Assemblies**. Angewandte Chemie International Edition 2022, 61 (47) https://doi.org/10.1002/anie.202212594
    77. Sergio Moles Quintero, Michael M. Haley, Miklos Kertesz, Juan Casado. Polycyclic Hydrocarbons from [4 n ]Annulenes: Correlation versus Hybridization Forces in the Formation of Diradicaloids. Angewandte Chemie 2022, 134 (44) https://doi.org/10.1002/ange.202209138
    78. Sergio Moles Quintero, Michael M. Haley, Miklos Kertesz, Juan Casado. Polycyclic Hydrocarbons from [4 n ]Annulenes: Correlation versus Hybridization Forces in the Formation of Diradicaloids. Angewandte Chemie International Edition 2022, 61 (44) https://doi.org/10.1002/anie.202209138
    79. Dimas G de Oteyza, Thomas Frederiksen. Carbon-based nanostructures as a versatile platform for tunable π-magnetism. Journal of Physics: Condensed Matter 2022, 34 (44) , 443001. https://doi.org/10.1088/1361-648X/ac8a7f
    80. David Jacob, Joaquín Fernández-Rossier. Theory of intermolecular exchange in coupled spin- 1 2 nanographenes. Physical Review B 2022, 106 (20) https://doi.org/10.1103/PhysRevB.106.205405
    81. Haipeng Wei, Xudong Hou, Tingting Xu, Ya Zou, Guangwu Li, Shaofei Wu, Yanhou Geng, Jishan Wu. Solution‐Phase Synthesis and Isolation of An Aza‐Triangulene and Its Cation in Crystalline Form. Angewandte Chemie 2022, 134 (40) https://doi.org/10.1002/ange.202210386
    82. Haipeng Wei, Xudong Hou, Tingting Xu, Ya Zou, Guangwu Li, Shaofei Wu, Yanhou Geng, Jishan Wu. Solution‐Phase Synthesis and Isolation of An Aza‐Triangulene and Its Cation in Crystalline Form. Angewandte Chemie International Edition 2022, 61 (40) https://doi.org/10.1002/anie.202210386
    83. Leoš Valenta, Michal Juríček. The taming of Clar's hydrocarbon. Chemical Communications 2022, 58 (78) , 10896-10906. https://doi.org/10.1039/D2CC03720C
    84. Tsuyoshi Murata, Kenta Yoshida, Shuichi Suzuki, Akira Ueda, Shinsuke Nishida, Junya Kawai, Kozo Fukui, Kazunobu Sato, Takeji Takui, Kazuhiro Nakasuji, Yasushi Morita. Double‐σ‐Bonded Close‐Shell Dimers and Peroxy‐Linked Open‐Shell Dimer Derived from a C 3 Symmetric Trioxophenalenyl Neutral Diradical. Chemistry – A European Journal 2022, 28 (52) https://doi.org/10.1002/chem.202201426
    85. Chi Zhang, Zewei Yi, Wei Xu. Scanning probe microscopy in probing low-dimensional carbon-based nanostructures and nanomaterials. Materials Futures 2022, 1 (3) , 032301. https://doi.org/10.1088/2752-5724/ac8a63
    86. Cui-Cui Yang, Xue-Lian Zheng, Jiu Chen, Wei Quan Tian, Wei-Qi Li, Ling Yang. Spin engineering of triangulenes and application for nano nonlinear optical materials design. Physical Chemistry Chemical Physics 2022, 24 (31) , 18529-18542. https://doi.org/10.1039/D2CP02915D
    87. Hazem Abdelsalam, Mohamed M. Atta, Vasil A. Saroka, Qinfang Zhang. Anomalous magnetic and transport properties of laterally connected graphene quantum dots. Journal of Materials Science 2022, 57 (30) , 14356-14370. https://doi.org/10.1007/s10853-022-07524-x
    88. Qin Xiang, Zhe Sun. Doublet Open‐Shell Graphene Fragments. Chemistry – An Asian Journal 2022, 17 (13) https://doi.org/10.1002/asia.202200251
    89. Yannick Carissan, Denis Hagebaum-Reignier, Nicolas Prcovic, Cyril Terrioux, Adrien Varet. How constraint programming can help chemists to generate Benzenoid structures and assess the local Aromaticity of Benzenoids. Constraints 2022, 27 (3) , 192-248. https://doi.org/10.1007/s10601-022-09328-x
    90. Marco Di Giovannantonio, Roman Fasel. On‐surface synthesis and atomic scale characterization of unprotected indenofluorene polymers. Journal of Polymer Science 2022, 60 (12) , 1814-1826. https://doi.org/10.1002/pol.20210902
    91. Kalyan Biswas, José I. Urgel, M. R. Ajayakumar, Ji Ma, Ana Sánchez‐Grande, Shayan Edalatmanesh, Koen Lauwaet, Pingo Mutombo, José M. Gallego, Rodolfo Miranda, Pavel Jelínek, Xinliang Feng, David Écija. Synthesis and Characterization of peri ‐Heptacene on a Metallic Surface. Angewandte Chemie 2022, 134 (23) https://doi.org/10.1002/ange.202114983
    92. Kalyan Biswas, José I. Urgel, M. R. Ajayakumar, Ji Ma, Ana Sánchez‐Grande, Shayan Edalatmanesh, Koen Lauwaet, Pingo Mutombo, José M. Gallego, Rodolfo Miranda, Pavel Jelínek, Xinliang Feng, David Écija. Synthesis and Characterization of peri ‐Heptacene on a Metallic Surface. Angewandte Chemie International Edition 2022, 61 (23) https://doi.org/10.1002/anie.202114983
    93. Si-Yu Li, Lin He. Recent progresses of quantum confinement in graphene quantum dots. Frontiers of Physics 2022, 17 (3) https://doi.org/10.1007/s11467-021-1125-2
    94. Prabhleen Kaur, Md. Ehesan Ali. The influence of the radicaloid character of polyaromatic hydrocarbon couplers on magnetic exchange interactions. Physical Chemistry Chemical Physics 2022, 24 (21) , 13094-13101. https://doi.org/10.1039/D1CP02044G
    95. F.A.L. de Souza, F.N.N. Pansini, L.F. Filho, Alan R. Ambrozio, J.C.C. Freitas, Wanderlã L. Scopel. NMR spectral parameters of open- and closed-shell graphene nanoflakes: Orbital and hyperfine contributions. Carbon 2022, 191 , 374-383. https://doi.org/10.1016/j.carbon.2022.01.045
    96. Khalid N. Anindya, Alain Rochefort. Controlling the magnetic properties of two-dimensional carbon-based Kagome polymers. Carbon Trends 2022, 7 , 100170. https://doi.org/10.1016/j.cartre.2022.100170
    97. Leoš Valenta, Maximilian Mayländer, Pia Kappeler, Olivier Blacque, Tomáš Šolomek, Sabine Richert, Michal Juríček. Trimesityltriangulene: a persistent derivative of Clar's hydrocarbon. Chemical Communications 2022, 58 (18) , 3019-3022. https://doi.org/10.1039/D2CC00352J
    98. Enquan Jin, Shuai Fu, Hiroki Hanayama, Matthew A. Addicoat, Wenxin Wei, Qiang Chen, Robert Graf, Katharina Landfester, Mischa Bonn, Kai A. I. Zhang, Hai I. Wang, Klaus Müllen, Akimitsu Narita. A Nanographene‐Based Two‐Dimensional Covalent Organic Framework as a Stable and Efficient Photocatalyst. Angewandte Chemie 2022, 134 (5) https://doi.org/10.1002/ange.202114059
    99. Enquan Jin, Shuai Fu, Hiroki Hanayama, Matthew A. Addicoat, Wenxin Wei, Qiang Chen, Robert Graf, Katharina Landfester, Mischa Bonn, Kai A. I. Zhang, Hai I. Wang, Klaus Müllen, Akimitsu Narita. A Nanographene‐Based Two‐Dimensional Covalent Organic Framework as a Stable and Efficient Photocatalyst. Angewandte Chemie International Edition 2022, 61 (5) https://doi.org/10.1002/anie.202114059
    100. R. Ortiz, J. C. Sancho-García, J. Fernández-Rossier. Frustrated magnetic interactions in a cyclacene crystal. Physical Review Materials 2022, 6 (1) https://doi.org/10.1103/PhysRevMaterials.6.014406
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