On-surface Synthesis of Graphene Nanoribbons

摘要
图/表
参考文献
相关文章 (0)

全文: PDF (712 KB) HTML (1 KB)
输出: BibTeX | EndNote (RIS)

摘要 On-surface synthesis never fails to fascinate chemists by producing new functional polymers which can hardly been prepared via traditional solution chemistry. Among those newly prepared polymers, graphene nanoribbons (GNRs), featured with tunable band gap, have attracted substantial attention because they are considered as promising candidates for next generation carbon-based semiconductors. Here, we summarize the recent advances of GNRs prepared on single crystal surfaces with emphasis on the structural tuning and electronic properties of GNRs. Moreover, critical developments toward the application of GNRs have also been reviewed including the mass fabrication and the performance of GNRs as field effect transistors.

	服务

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	E-mail Alert
	RSS
	作者相关文章
	唐雁宁
	孙科伟
	李雪超
	张海明
	迟力峰

关键词 ： graphene nanoribbons (GNRs), on-surface reactions, scanning tunneling microscopy (STM), scanning tunneling spectroscopy (STS)

Abstract：On-surface synthesis never fails to fascinate chemists by producing new functional polymers which can hardly been prepared via traditional solution chemistry. Among those newly prepared polymers, graphene nanoribbons (GNRs), featured with tunable band gap, have attracted substantial attention because they are considered as promising candidates for next generation carbon-based semiconductors. Here, we summarize the recent advances of GNRs prepared on single crystal surfaces with emphasis on the structural tuning and electronic properties of GNRs. Moreover, critical developments toward the application of GNRs have also been reviewed including the mass fabrication and the performance of GNRs as field effect transistors.

Key words： graphene nanoribbons (GNRs) on-surface reactions scanning tunneling microscopy (STM) scanning tunneling spectroscopy (STS)

收稿日期: 2020-07-22 出版日期: 2020-08-12

基金资助:Supported by National Key R&D Program of China (2016YFB0700600), Soft Science Research Project of Guangdong Province (No. 2017B030301013), and Shenzhen Science and Technology Research Grant (ZDSYS201707281026184)

通讯作者: hmzhang@suda.edu.cn and chilf@suda.edu.cn E-mail: hmzhang@suda.edu.cn and chilf@suda.edu.cn

引用本文:

唐雁宁;孙科伟;李雪超;张海明;迟力峰. On-surface Synthesis of Graphene Nanoribbons[J]. 结构化学, 2020, 39(8): 1377-1384.
TANG Yan-Ning;SUN Ke-Wei;LI Xue-Chao;ZHANG Hai-Ming;CHI Li-Feng. On-surface Synthesis of Graphene Nanoribbons. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(8): 1377-1384.

链接本文:

http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I8/1377

REFERENCES
(1) Cai, J. M.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg, S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X. L.; Mullen, K.; Fasel, R. Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 2010, 466, 470–473.
(2) Talirz, L.; Sde, H.; Kawai, S.; Ruffieux, P.; Meyer, E.; Feng, X. L.; Mllen, K.; Fasel, R.; Pignedoli, C. A.; Passerone, D. Band gap of atomically precise graphene nanoribbons as a function of ribbon length and termination. Chemphyschem 2019, 20, 2348–2353.
(3) Sun, K. W.; Ji, P. H.; Zhang, J. J.; Wang, J. X.; Li, X. C.; Xu, X.; Zhang, H. M.; Chi, L. F. On-surface synthesis of 8- and 10-armchair graphene nanoribbons. Small 2019, 15, 1804526.
(4) Zhang, H. M.; Lin, H. P.; Sun, K. W.; Chen, L.; Zagranyarski, Y.; Aghdassi, N.; Duhm, S.; Li, Q.; Zhong, D. Y.; Li, Y. Y.; Mullen, K.; Fuchs, H.; Chi, L. F. On-surface synthesis of rylene-type graphene nanoribbons. J. Am. Chem. Soc. 2015, 137, 4022–4025.
(5) Kimouche, A.; Ervasti, M. M.; Drost, R.; Halonen, S.; Harju, A.; Joensuu, P. M.; Sainio, J.; Liljeroth, P. Ultra-narrow metallic armchair graphene nanoribbons. Nat. Commun. 2015, 6, 10177.
(6) Beyer, D.; Wang, S. Y.; Pignedoli, C. A.; Melidonie, J.; Yuan, B. K.; Li, C.; Wilhelm, J.; Ruffieux, P.; Berger, R.; Mullen, K.; Fasel, R.; Feng, X. L. Graphene nanoribbons derived from zigzag edge-encased poly(para–2,9-dibenzo[bc,kl]coronenylene) polymer chains. J. Am. Chem. Soc. 2019, 141, 4488–4488.
(7) Ruffieux, P.; Wang, S. Y.; Yang, B.; Sanchez-Sanchez, C.; Liu, J.; Dienel, T.; Talirz, L.; Shinde, P.; Pignedoli, C. A.; Passerone, D.; Dumslaff, T.; Feng, X. L.; Mullen, K.; Fasel, R. On-surface synthesis of graphene nanoribbons with zigzag edge topology. Nature 2016, 531, 489–492.
(8) Liu, J. Z.; Li, B. W.; Tan, Y. Z.; Giannakopoulos, A.; Sanchez-Sanchez, C.; Beljonne, D.; Ruffieux, P.; Fasel, R.; Feng, X. L.; Mullen, K. Toward cove-edged low band gap graphene nanoribbons. J. Am. Chem. Soc. 2015, 137, 6097–6103.
(9) Yang, L.; Park, C. H.; Son, Y. W.; Cohen, M. L.; Louie, S. G. Quasiparticle energies and band gaps in graphene nanoribbons. Phys. Rev. Lett. 2007, 99, 186801.
(10) Yang, X. Y.; Dou, X.; Rouhanipour, A.; Zhi, L. J.; Rader, H. J.; Mullen, K. Two-dimensional graphene nanoribbons. J. Am. Chem. Soc. 2008, 130, 4216–4217.
(11) Jiao, L. Y.; Zhang, L.; Wang, X. R.; Diankov, G.; Dai, H. J. Narrow graphene nanoribbons from carbon nanotubes. Nature 2009, 458, 877–880.
(12) Chen, Y. C.; de Oteyza, D. G.; Pedramrazi, Z.; Chen, C.; Fischer, F. R.; Crommie, M. F. Tuning the band gap of graphene nanoribbons synthesized from molecular precursors. ACS Nano 2013, 7, 6123–6128.
(13) Wang, X. Y.; Dienel, T.; Di Giovannantonio, M.; Barin, G. B.; Kharche, N.; Deniz, O.; Urgel, J. I.; Widmer, R.; Stolz, S.; De Lima, L. H.; Muntwiler, M.; Tommasini, M.; Meunier, V.; Ruffieux, P.; Feng, X. L.; Fasel, R.; Mullen, K.; Narita, A. Heteroatom-doped perihexacene from a double helicene precursor: on-surface synthesis and properties. J. Am. Chem. Soc. 2017, 139, 4671–4674.
(14) Kawai, S.; Saito, S.; Osumi, S.; Yamaguchi, S.; Foster, A. S.; Spijker, P.; Meyer, E. Atomically controlled substitutional boron-doping of graphene nanoribbons. Nat. Commun. 2015, 6, 8098.
(15) Teeter, J. D.; Costa, P. S.; Pour, M. M.; Miller, D. P.; Zurek, E.; Enders, A.; Sinitskii, A. Epitaxial growth of aligned atomically precise chevron graphene nanoribbons on Cu(111). Chem. Commun. 2017, 53, 8463–8466.
(16) Carbonell-Sanroma, E.; Hieulle, J.; Vilas-Varela, M.; Brandimarte, P.; Lraola, M.; Barragan, A.; Li, J. C.; Abadia, M.; Corso, M.; Sanchez-Portal, D.; Pena, D.; Pascual, J. I. Doping of graphene nanoribbons via functional group edge modification. ACS Nano 2017, 11, 7355–7361.
(17) Marangoni, T.; Haberer, D.; Rizzo, D. J.; Cloke, R. R.; Fischer, F. R. Heterostructures through divergent edge reconstruction in nitrogen-doped segmented graphene nanoribbons. Chem.-Eur. J. 2016, 22, 13037–13040.
(18) Zhang, Y.; Zhang, Y. F.; Li, G.; Lu, J. C.; Lin, X.; Du, S. X.; Berger, R.; Feng, X. L.; Mullen, K.; Gao, H. J. Direct visualization of atomically precise nitrogen-doped graphene nanoribbons. Appl. Phys. Lett. 2014, 105, 023101.
(19) Nguyen, G. D.; Tom, F. M.; Cao, T.; Pedramrazi, Z.; Chen, C.; Rizzo, D. J.; Joshi, T.; Bronner, C.; Chen, Y. C.; Favaro, M.; Louie, S. G.; Fischer, F. R.; Crommie, M. F. Bottom-up synthesis of n = 13 sulfur-doped graphene nanoribbons. J. Phys. Chem. C 2016, 120, 2684–2687.
(20) Wang, X. Y.; Yao, X. L.; Narita, A.; Mullen, K. Heteroatom-doped nanographenes with structural precision. Acc. Chem. Res. 2019, 52, 2491–2505.
(21) Liu, M. Z.; Liu, M. X.; Zha, Z. Q.; Pan, J. L.; Qiu, X. H.; Li, T.; Wang, J. B.; Zheng, Y.; Zhong, D. Y. Thermally induced transformation of nonhexagonal carbon rings in graphene-like nanoribbons. J. Phys. Chem. C 2018, 122, 9586–9592.
(22) Fan, Q.; Martin-Jimenez, D.; Ebeling, D.; Krug, C. K.; Brechmann, L.; Kohlmeyer, C.; Hilt, G.; Hieringer, W.; Schirmeisen, A.; Gottfried, J. M. Nanoribbons with nonalternant topology from fusion of polyazulene: carbon allotropes beyond graphene. J. Am. Chem. Soc. 2019, 141, 17713–17720.
(23) Hou, I. C. Y.; Sun, Q.; Eimre, K.; Di Giovannantonio, M.; Urgel, J. I.; Ruffieux, P.; Narita, A.; Fasel, R.; Müllen, K. On-surface synthesis of unsaturated carbon nanostructures with regularly fused pentagon-heptagon pairs. J. Am. Chem. Soc. 2020, 142, 10291–10296.
(24) Di Giovannantonio, M.; Urgel, J. I.; Beser, U.; Yakutovich, A. V.; Wilhelm, J.; Pignedoli, C. A.; Ruffieux, P.; Narita, A.; Mullen, K.; Fasel, R. On-surface synthesis of indenofluorene polymers by oxidative five-membered ring formation. J. Am. Chem. Soc. 2018, 140, 3532–3536.
(25) Majzik, Z.; Pavlicek, N.; Vilas-Varela, M.; Perez, D.; Moll, N.; Guitian, E.; Meyer, G.; Pena, D.; Gross, L. Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces. Nat. Commun. 2018, 9, 1198.
(26) Riss, A.; Wickenburg, S.; Gorman, P.; Tan, L. Z.; Tsai, H. Z.; de Oteyza, D. G.; Chen, Y. C.; Bradley, A. J.; Ugeda, M. M.; Etkin, G.; Louie, S. G.; Fischer, F. R.; Crommie, M. F. Local electronic and chemical structure of oligo-acetylene derivatives formed through radical cyclizations at a surface. Nano. Lett. 2014, 14, 2251–2255.
(27) Liu, M. Z.; Liu, M. X.; She, L. M.; Zha, Z. Q.; Pan, J. L.; Li, S. C.; Li, T.; He, Y. Y.; Cai, Z. Y.; Wang, J. B.; Zheng, Y.; Qiu, X. H.; Zhong, D. Y. Graphene-like nanoribbons periodically embedded with four- and eight-membered rings. Nat. Commun. 2017, 8, 14924.
(28) Kawai, S.; Takahashi, K.; Ito, S.; Pawlak, R.; Meier, T.; Spijker, P.; Canova, F. F.; Tracey, J.; Nozaki, K.; Foster, A. S.; Meyer, E. Competing annulene and radialene structures in a single anti-aromatic molecule studied by high-resolution atomic force microscopy. ACS Nano 2017, 11, 8122–8130.
(29) Cho, J.; Smerdon, J.; Gao, L.; Suzer, O.; Guest, J. R.; Guisinger, N. P. Structural and electronic decoupling of c–60 from epitaxial graphene on sic. Nano. Lett. 2012, 12, 3018–3024.
(30) Repp, J.; Meyer, G.; Stojkovic, S. M.; Gourdon, A.; Joachim, C. Molecules on insulating films: scanning-tunneling microscopy imaging of individual molecular orbitals. Phys. Rev. Lett. 2005, 94, 026803.
(31) Zheng, Y. J.; Huang, Y. L.; Chenp, Y. F.; Zhao, W. J.; Eda, G.; Spataru, C. D.; Zhang, W. J.; Chang, Y. H.; Li, L. J.; Chi, D. Z.; Quek, S. Y.; Wee, A. T. S. Heterointerface screening effects between organic monolayers and monolayer transition metal dichalcogenides. ACS Nano 2016, 10, 2476–2484.
(32) Liu, Z. H.; Sun, K. W.; Li, X. C.; Li, L.; Zhang, H. M.; Chi, L. F. Electronic decoupling of organic layers by a self-assembled supramolecular network on au(111). J. Phys. Chem. Lett. 2019, 10, 4297–4302.
(33) Han, P.; Akagi, K.; Canova, F. F.; Mutoh, H.; Shiraki, S.; Iwaya, K.; Weiss, P. S.; Asao, N.; Hitosugi, T. Bottom-up graphene-nanoribbon fabrication reveals chiral edges and enantioselectivity. ACS Nano 2014, 8, 9181–9187.
(34) Basagni, A.; Sedona, F.; Pignedoli, C. A.; Cattelan, M.; Nicolas, L.; Casarin, M.; Sambi, M. Molecules-oligomers-nanowires-graphene nanoribbons: a bottom-up stepwise on-surface covalent synthesis preserving long-range order. J. Am. Chem. Soc. 2015, 137, 1802–1808
(35) Zhang, Y. F.; Zhang, Y.; Li, G.; Lu, J. C.; Que, Y. D.; Chen, H.; Berger, R.; Feng, X. L.; Mullen, K.; Lin, X.; Zhang, Y. Y.; Du, S. X.; Pantelides, S. T.; Gao, H. J. Sulfur-doped graphene nanoribbons with a sequence of distinct band gaps. Nano Res. 2017, 10, 3377–3384
(36) Bronner, C.; Leyssner, F.; Stremlau, S.; Utecht, M.; Saalfrank, P.; Klamroth, T.; Tegeder, P. Electronic structure of a subnanometer wide bottom-up fabricated graphene nanoribbon: end states, band gap, and dispersion. Phys. Rev. B 2012, 86, 085444.
(37) Kleimeier, N. F.; Timmer, A.; Bignardi, L.; Monig, H.; Feng, X. L.; Mullen, K.; Chi, L. F.; Fuchs, H.; Zacharias, H. Electron dynamics in unoccupied states of spatially aligned 7-a graphene nanoribbons on au(788). Phys. Rev. B 2014, 90, 245408.
(38) Linden, S.; Zhong, D.; Timmer, A.; Aghdassi, N.; Franke, J. H.; Zhang, H.; Feng, X.; Mullen, K.; Fuchs, H.; Chi, L.; Zacharias, H. Electronic structure of spatially aligned graphene nanoribbons on au(788). Phys. Rev. Lett. 2012, 108, 216801.
(39) Chen, Y. C.; Cao, T.; Chen, C.; Pedramrazi, Z.; Haberer, D.; de Oteyza, D. G.; Fischer, F. R.; Louie, S. G.; Crommie, M. F. Molecular bandgap engineering of bottom-up synthesized graphene nanoribbon heterojunctions. Nat. Nanotech. 2015, 10, 156–160.
(40) Mishra, S.; Lohr, T. G.; Pignedoli, C. A.; Liu, J. Z.; Berger, R.; Urgel, J. I.; Mullen, K.; Feng, X. L.; Ruffieux, P.; Fasel, R. Tailoring bond topologies in open-shell graphene nanostructures. ACS Nano 2018, 12, 11917–11927.
(41) Mishra, S.; Beyer, D.; Berger, R.; Liu, J. Z.; Groning, O.; Urgel, J. I.; Mullen, K.; Ruffieux, P.; Feng, X. L.; Fasel, R. Topological defect-induced magnetism in a nanographene. J. Am. Chem. Soc. 2020, 142, 1147–1152.
(42) Merino-Diez, N.; Garcia-Lekue, A.; Carbonell-Sanroma, E.; Li, J. C.; Corso, M.; Colazzo, L.; Sedona, F.; Sanchez-Portal, D.; Pascual, J. I.; de Oteyza, D. G. Width-dependent band gap in armchair graphene nanoribbons reveals fermi level pinning on au(111). ACS Nano 2017, 11, 11661–11668.
(43) Ruffieux, P.; Cai, J. M.; Plumb, N. C.; Patthey, L.; Prezzi, D.; Ferretti, A.; Molinari, E.; Feng, X. L.; Mullen, K.; Pignedoli, C. A.; Fasel, R. Electronic structure of atomically precise graphene nanoribbons. ACS Nano 2012, 6, 6930–6935.
(44) Huang, H.; Chen, S.; Gao, X. Y.; Chen, W.; Wee, A. T. S. Structural and electronic properties of ptcda thin films on epitaxial graphene. ACS Nano 2009, 3, 3431–3436.
(45) Liu, L. W.; Dienel, T.; Widmer, R.; Groning, O. Interplay between energy-level position and charging effect of manganese phthalocyanines on an atomically thin insulator. ACS Nano 2015, 9, 10125–10132.
(46) Wang, S. Y.; Talirz, L.; Pignedoli, C. A.; Feng, X. L.; Mullen, K.; Fasel, R.; Ruffieux, P. Giant edge state splitting at atomically precise graphene zigzag edges. Nat. Commun. 2016, 7, 11507.
(47) Yamaguchi, J.; Hayashi, H.; Jippo, H.; Shiotari, A.; Ohtomo, M.; Sakakura, M.; Hieda, N.; Aratani, N.; Ohfuchi, M.; Sugimoto, Y.; Yamada, H.; Sato, S. Small bandgap in atomically precise 17-atom-wide armchair-edged graphene nanoribbons. Commun. Mater. 2020, 1, DOI 10.1038/s43246-020-0039-9.
(48) Sakaguchi, H.; Kawagoe, Y.; Hirano, Y.; Iruka, T.; Yano, M.; Nakae, T. Width-controlled sub-nanometer graphene nanoribbon films synthesized by radical-polymerized chemical vapor deposition. Adv. Mater. 2014, 26, 4134–4138.
(49) Narita, A.; Chen, Z. P.; Chen, Q.; Mullen, K. Solution and on-surface synthesis of structurally defined graphene nanoribbons as a new family of semiconductors. Chem. Sci. 2019, 10, 964–975.
(50) Sakaguchi, H.; Song, S. T.; Kojima, T.; Nakae, T. Homochiral polymerization-driven selective growth of graphene nanoribbons. Nat. Chem. 2017, 9, 57–63.
(51) Song, S. T.; Kojima, T.; Nakae, T.; Sakaguchi, H. Wide graphene nanoribbons produced by interchain fusion of poly(p-phenylene) via two-zone chemical vapor deposition. Chem. Commun. 2017, 53, 7034–7036.
(52) Bennett, P. B.; Pedramrazi, Z.; Madani, A.; Chen, Y. C.; de Oteyza, D. G.; Chen, C.; Fischer, F. R.; Crommie, M. F.; Bokor, J. Bottom-up graphene nanoribbon field-effect transistors. Appl. Phys. Lett. 2013, 103, 253114.
(53) Chen, Z. P.; Zhang, W.; Palma, C. A.; Rizzini, A. L.; Liu, B. L.; Abbas, A.; Richter, N.; Martini, L.; Wang, X. Y.; Cavani, N.; Lu, H.; Mishra, N.; Coletti, C.; Berger, R.; Klappenberger, F.; Klaui, M.; Candini, A.; Affronte, M.; Zhou, C. W.; De Renzi, V.; del Pennino, U.; Barth, J. V.; Rader, H. J.; Narita, A.; Feng, X. L.; Mullen, K. Synthesis of graphene nanoribbons by ambient-pressure chemical vapor deposition and device integration. J. Am. Chem. Soc. 2016, 138, 15488–15496.
(54) Kojima, T.; Bao, Y.; Zhang, C.; Liu, S. L.; Xu, H.; Nakae, T.; Loh, K. P.; Sakaguchi, H. Orientation and electronic structures of multilayered graphene nanoribbons produced by two-zone chemical vapor deposition. Langmuir 2017, 33, 10439–10445.
(55) Ohtomo, M.; Sekine, Y.; Hibino, H.; Yamamoto, H. Graphene nanoribbon field-effect transistors fabricated by etchant-free transfer from au(788). Appl. Phys. Lett. 2018, 112, 021602.
(56) Liu, Y.; Wang, X. Z.; Dong, Y. F.; Wang, Z. Y.; Zhao, Z. B.; Qiu, J. S. Nitrogen-doped graphene nanoribbons for high-performance lithium ion batteries. J. Mater. Chem. A 2014, 2, 16832–16835.
(57) Liu, M. K.; Song, Y. F.; He, S. X.; Tjiu, W. W.; Pan, J. S.; Xia, Y. Y.; Liu, T. X. Nitrogen-doped graphene nanoribbons as efficient metal-free electrocatalysts for oxygen reduction. Acs Appl. Mater. Inter. 2014, 6, 4214–4222.