Top

Published in:

2018 | OriginalPaper | Chapter

On-Surface Synthesis of Two-Dimensional Polymers: Rational Design and Electronic Properties

Author : Sabine Maier

Published in: On-Surface Synthesis II

Publisher: Springer International Publishing

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

The fabrication of long-range ordered 2D polymers directly on metal surfaces still presents a great challenge in ultra-high vacuum surface science. The structure of the polymer networks is in general predetermined by the coupling chemistry and the symmetry of the molecular precursors. However, the irreversible nature of the C–C coupling reaction readily leads to the formation of defects. Over the last decade, several strategies in the on-surface synthesis have been suggested to improve the structural order. Among them, the programmed hierarchical synthesis through a sequential polymerization proved to be suitable to reduce defects in the formation of 2D polymers. This chapter provides a review on the state-of-the-art structural characterization of surface-supported 2D polymers by established surface science techniques. Further, the chapter focuses on the electronic structure of 2D polymers, which remained experimentally widely unexplored until now.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 340 Zeitschriften

aus folgenden Fachgebieten:

Bauwesen + Immobilien
Business IT + Informatik
Finance + Banking
Management + Führung
Marketing + Vertrieb
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

previous chapter Aryl–Aryl Covalent Coupling on Rutile TiO2 Surfaces

next chapter On-Surface Coupling Reactions with Extrinsic Catalysts

Sakamoto, J., van Heijst, J., Lukin, O., Schlüter, A.D.: Two-dimensional polymers: just a dream of synthetic chemists? Angew. Chem. Int. Ed. 48, 1030–1069 (2009)CrossRef

Colson, J.W., Dichtel, W.R.: Rationally synthesized two-dimensional polymers. Nat. Chem. 5, 453–465 (2013)CrossRef

Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A.P., Saleh, M., Feng, X., et al.: Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466, 470–473 (2010)CrossRef

Talirz, L., Ruffieux, P., Fasel, R.: On-surface synthesis of atomically precise graphene nanoribbons. Adv. Mater. 28, 6222–6231 (2016)CrossRef

Söde, H., Talirz, L., Gröning, O., Pignedoli, C.A., Berger, R., Feng, X., Müllen, K., Fasel, R., Ruffieux, P.: Electronic band dispersion of graphene nanoribbons via Fourier-transformed scanning tunneling spectroscopy. Phys. Rev. B 91, 045429 (2015)

Cai, J., Pignedoli, C.A., Talirz, L., Ruffieux, P., Söde, H., Liang, L., Meunier, V., Berger, R., Li, R., Feng, X., et al.: Graphene nanoribbon heterojunctions. Nat. Nanotechnol. 9, 896–900 (2014)CrossRef

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 7, 6123–6128 (2013)CrossRef

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. Nanotechnol. 10, 156–160 (2015)CrossRef

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. 6, 8098 (2015)CrossRef

10.

Cloke, R.R., Marangoni, T., Nguyen, G.D., Joshi, T., Rizzo, D.J., Bronner, C., Cao, T., Louie, S.G., Crommie, M.F., Fischer, F.R.: Site-specific substitutional Boron doping of semiconducting armchair graphene nanoribbons. J. Am. Chem. Soc. 137, 8872–8875 (2015)CrossRef

11.

van der Lit, J., Boneschanscher, M.P., Vanmaekelbergh, D., Ijäs, M., Uppstu, A., Ervasti, M., Harju, A., Liljeroth, P., Swart, I.: Suppression of electron-vibron coupling in graphene nanoribbons contacted via a single atom. Nat. Commun. 4, 2023 (2013)

12.

Held, P.A., Fuchs, H., Studer, A.: Covalent-bond formation via on-surface chemistry. Chem. Eur. J. 23, 5874–5892 (2017)CrossRef

13.

Whitelam, S., Tamblyn, I., Haxton, T.K., Wieland, M.B., Champness, N.R., Garrahan, J.P., Beton, P.H.: Common physical framework explains phase behavior and dynamics of atomic, molecular, and polymeric network formers. Phys. Rev. X 4, 011044 (2014)

14.

Pedersen, T.G., Flindt, C., Pedersen, J., Mortensen, N.A., Jauho, A.-P., Pedersen, K.: Graphene antidot lattices: designed defects and spin qubits. Phys. Rev. Lett. 100, 136804 (2008)CrossRef

15.

Adjizian, J.-J., Briddon, P., Humbert, B., Duvail, J.-L., Wagner, P., Adda, C., Ewels, C.: Dirac cones in two-dimensional conjugated polymer networks. Nat. Commun. 5, 5842 (2014)CrossRef

16.

Adjizian, J.-J., Lherbier, A., M.-M., Dubois, S., Botello-Mendez, A.R., Charlier, J.-C.: The electronic and transport properties of two-dimensional conjugated polymer networks including disorder. Nanoscale, 8, 1642–1651 (2016)

17.

Malko, D., Neiss, C., Viñes, F., Görling, A.: Competition for graphene: graphynes with direction-dependent Dirac cones. Phys. Rev. Lett. 108, 086804 (2012)

18.

Perepichka, D.F., Rosei, F.: Extending polymer conjugation into the second dimension. Science 323, 216 (2009)CrossRef

19.

Blankenburg, S., Bieri, M., Fasel, R., Müllen, K., Pignedoli, C.A., Passerone, D.: Porous graphene as an atmospheric nanofilter. Small 6, 2266–2271 (2010)CrossRef

20.

Xiang, Z., Cao, D., Dai, L.: Well-defined two dimensional covalent organic polymers: rational design, controlled syntheses, and potential applications. Polym. Chem. 6, 1896–1911 (2015)CrossRef

21.

Narita, A., Wang, X.-Y., Feng, X., Mullen, K.: New advances in nanographene chemistry. Chem. Soc. Rev. 44, 6616–6643 (2015)CrossRef

22.

Li, Y., Xu, L., Liu, H., Li, Y.: Graphdiyne and graphyne: from theoretical predictions to practical construction. Chem. Soc. Rev. 43, 2572–2586 (2014)CrossRef

23.

Gourdon, A.: On-surface covalent coupling in ultrahigh vacuum. Angew. Chem. Int. Ed. 47, 6950–6953 (2008)CrossRef

24.

Fan, Q., Gottfried, J.M., Zhu, J.: Surface-catalyzed C-C covalent coupling strategies toward the synthesis of low-dimensional carbon-based nanostructures. Acc. Chem. Res. 48, 2484–2494 (2015)CrossRef

25.

Dong, L., Liu, P.N., Lin, N.: Surface-activated coupling reactions confined on a surface. Acc. Chem. Res. 48, 2765–2774 (2015)CrossRef

26.

Björk, J., Hanke, F.: Towards design rules for covalent nanostructures on metal surfaces. Chem. Eur. J. 20, 928–934 (2014)CrossRef

27.

Lindner, R., Rahe, P., Kittelmann, M., Gourdon, A., Bechstein, R., Kühnle, A.: Substrate templating guides the photoinduced reaction of C₆₀ on calcite. Angew. Chem. Int. Ed. 53, 7952–7955 (2014)CrossRef

28.

Palma, C.-A., Diller, K., Berger, R., Welle, A., Björk, J., Cabellos, J.L., Mowbray, D.J., Papageorgiou, A.C., Ivleva, N.P., Matich, S., et al.: Photoinduced C-C reactions on insulators toward photolithography of graphene nanoarchitectures. J. Am. Chem. Soc. 136, 4651–4658 (2014)CrossRef

29.

Kawai, S.: Revealing mechanical and structural properties of molecules on surface by high-resolution atomic force microscopy. Polym. J. 49, 3–11 (2017)CrossRef

30.

Gross, L.: Recent advances in submolecular resolution with scanning probe microscopy. Nat. Chem. 3, 273–278 (2011)CrossRef

31.

Zwaneveld, N.A.A., Pawlak, R., Abel, M., Catalin, D., Gigmes, D., Bertin, D., Porte, L.: Organized formation of 2D extended covalent organic frameworks at surfaces. J. Am. Chem. Soc. 130, 6678–6679 (2008)CrossRef

32.

Côté, A.P., Benin, A.I., Ockwig, N.W., O’Keeffe, M., Matzger, A.J., Yaghi, O.M.: Porous, crystalline. Covalent organic frameworks. Science 310, 1166–1170 (2005)CrossRef

33.

Weigelt, S., Busse, C., Bombis, C., Knudsen, M.M., Gothelf, K.V., Lægsgaard, E., Besenbacher, F., Linderoth, T.R.: Surface synthesis of 2D branched polymer nanostructures. Angew. Chem. Int. Ed. 47, 4406–4410 (2008)CrossRef

34.

Schlögl, S., Heckl, W.M., Lackinger, M.: On-surface radical addition of triply iodinated monomers on Au(111)—the influence of monomer size and thermal post-processing. Surf. Sci. 606, 999–1004 (2012)CrossRef

35.

Eichhorn, J., Nieckarz, D., Ochs, O., Samanta, D., Schmittel, M., Szabelski, P.J., Lackinger, M.: On-surface Ullmann coupling: the influence of kinetic reaction parameters on the morphology and quality of covalent networks. ACS Nano 8, 7880–7889 (2014)CrossRef

36.

Bieri, M., Nguyen, M.-T., Gröning, O., Cai, J., Treier, M., Aït-Mansour, K., Ruffieux, P., Pignedoli, C.A., Passerone, D., Kastler, M., et al.: Two-dimensional polymer formation on surfaces: insight into the roles of precursor mobility and reactivity. J. Am. Chem. Soc. 132, 16669–16676 (2010)CrossRef

37.

Grill, L., Dyer, M., Lafferentz, L., Persson, M., Peters, M.V., Hecht, S.: Nano-architectures by covalent assembly of molecular building blocks. Nat. Nanotechnol. 2, 687–691 (2007)CrossRef

38.

Bieri, M., Treier, M., Cai, J., Ait-Mansour, K., Ruffieux, P., Groning, O., Groning, P., Kastler, M., Rieger, R., Feng, X., et al.: Porous graphenes: two-dimensional polymer synthesis with atomic precision. Chem. Commun. 6919–6921 (2009)

39.

Liu, J., Ruffieux, P., Feng, X., Müllen, K., Fasel, R.: Cyclotrimerization of arylalkynes on Au(111). Chem. Commun. 50, 11200–11203 (2014)CrossRef

40.

Yang, B., Björk, J., Lin, H., Zhang, X., Zhang, H., Li, Y., Fan, J., Li, Q., Chi, L.: Synthesis of surface covalent organic frameworks via dimerization and cyclotrimerization of acetyls. J. Am. Chem. Soc. 137, 4904–4907 (2015)CrossRef

41.

Liu, J., Ruffieux, P., Feng, X., Müllen, K., Fasel, R.: Cyclotrimerization of arylalkynes on Au(111). Chem. Commun. 50, 11200–11203 (2014)CrossRef

42.

Eichhorn, J., Strunskus, T., Rastgoo-Lahrood, A., Samanta, D., Schmittel, M., Lackinger, M.: On-surface Ullmann polymerization via intermediate organometallic networks on Ag(111). Chem. Commun. 50, 7680–7682 (2014)CrossRef

43.

Biradha, K., Santra, R.: Crystal engineering of topochemical solid state reactions. Chem. Soc. Rev. 42, 950–967 (2013)CrossRef

44.

Ruffieux, P., Wang, S., Yang, B., Sánchez-Sánchez, C., Liu, J., Dienel, T., Talirz, L., Shinde, P., Pignedoli, C.A., Passerone, D., et al.: On-surface synthesis of graphene nanoribbons with zigzag edge topology. Nature 531, 489–492 (2016)CrossRef

45.

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. 137, 1802–1808 (2015)CrossRef

46.

Zhang, H., Franke, J.-H., Zhong, D., Li, Y., Timmer, A., Arado, O.D., Mönig, H., Wang, H., Chi, L., Wang, Z., et al.: Surface supported gold-organic hybrids: on-surface synthesis and surface directed orientation. Small 10, 1361–1368 (2014)CrossRef

47.

Lafferentz, L., Eberhardt, V., Dri, C., Africh, C., Comelli, G., Esch, F., Hecht, S., Grill, L.: Controlling on-surface polymerization by hierarchical and substrate-directed growth. Nat. Chem. 4, 215–220 (2012)CrossRef

48.

Shi, K.J., Zhang, X., Shu, C.H., Li, D.Y., Wu, X.Y., Liu, P.N.: Ullmann coupling reaction of aryl chlorides on Au(111) using dosed Cu as a catalyst and the programmed growth of 2D covalent organic frameworks. Chem. Commun. 52, 8726–8729 (2016)

49.

Steiner, C., Gebhardt, J., Ammon, M., Yang, Z., Heidenreich, A., Hammer, N., Görling, A., Kivala, M., Maier, S.: Hierarchical on-surface synthesis and electronic structure of carbonyl-functionalized one- and two-dimensional covalent nanoarchitectures. Nat. Commun. 8, 14765 (2017)CrossRef

50.

Fan, Q., Wang, C., Han, Y., Zhu, J., Hieringer, W., Kuttner, J., Hilt, G., Gottfried, J.M.: Surface-assisted organic synthesis of hyperbenzene nanotroughs. Angew. Chem. Int. Ed. 52, 4668–4672 (2013)CrossRef

51.

Chen, M., Shang, J., Wang, Y., Wu, K., Kuttner, J., Hilt, G., Hieringer, W., Gottfried, J.M.: On-Surface synthesis and characterization of honeycombene oligophenylene macrocycles. ACS Nano 11, 134–143 (2017)CrossRef

52.

Vasseur, G., Fagot-Revurat, Y., Sicot, M., Kierren, B., Moreau, L., Malterre, D., Cardenas, L., Galeotti, G., Lipton-Duffin, J., Rosei, F., et al.: Quasi one-dimensional band dispersion and surface metallization in long-range ordered polymeric wires. Nat. Commun. 7, 10235 (2016)CrossRef

53.

Gutzler, R., Perepichka, D.F.: π-electron conjugation in two dimensions. J. Am. Chem. Soc. 135, 16585–16594 (2013)CrossRef

54.

Wen, J., Luo, D., Cheng, L., Zhao, K., Ma, H.: Electronic structure properties of two-dimensional π-conjugated polymers. Macromolecules 49, 1305–1312 (2016)CrossRef

55.

Cardenas, L., Gutzler, R., Lipton-Duffin, J., Fu, C., Brusso, J.L., Dinca, L.E., Vondracek, M., Fagot-Revurat, Y., Malterre, D., Rosei, F., et al.: Synthesis and electronic structure of a two dimensional π-conjugated polythiophene. Chem. Sci. 4, 3263–3268 (2013)CrossRef

56.

Baryshnikov, G.V., Minaev, B.F., Karaush, N.N., Minaeva, V.A.: The art of the possible: computational design of the 1D and 2D materials based on the tetraoxa[8]circulene monomer. RSC Adv. 4, 25843–25851 (2014)CrossRef

57.

Wiengarten, A., Seufert, K., Auwärter, W., Ecija, D., Diller, K., Allegretti, F., Bischoff, F., Fischer, S., Duncan, D.A., Papageorgiou, A.C., et al.: Surface-assisted dehydrogenative homocoupling of porphine molecules. J. Am. Chem. Soc. 136, 9346–9354 (2014)CrossRef

58.

Morchutt, C., Björk, J., Straßer, C., Starke, U., Gutzler, R., Kern, K.: Interplay of chemical and electronic structure on the single-molecule level in 2D polymerization. ACS Nano 10, 11511–11518 (2016)CrossRef

59.

Sánchez-Sánchez, C., Brüller, S., Sachdev, H., Müllen, K., Krieg, M., Bettinger, H.F., Nicolaï, A., Meunier, V., Talirz, L., Fasel, R., et al.: On-surface synthesis of BN-substituted heteroaromatic networks. ACS Nano 9, 9228–9235 (2015)CrossRef

60.

Bieri, M., Blankenburg, S., Kivala, M., Pignedoli, C.A., Ruffieux, P., Müllen, K., Fasel, R.: Surface-supported 2D heterotriangulene polymers. Chem. Comm. 47, 10239–10241 (2011)CrossRef

61.

Faury, T., Dumur, F., Clair, S., Abel, M., Porte, L., Gigmes, D.: Side functionalization of diboronic acid precursors for covalent organic frameworks. CrystEngComm 15, 2067–2075 (2013)CrossRef

62.

Xu, L., Cao, L., Guo, Z., Zha, Z., Lei, S.: Side-functionalized two-dimensional polymers synthesized via on-surface Schiff-base coupling. Chem. Comm. 51, 8664–8667 (2015)CrossRef

63.

Teyssandier, J., Feyter, S.D., Mali, K.S.: Host-guest chemistry in two-dimensional supramolecular networks. Chem. Comm. 52, 11465–11487 (2016)CrossRef

64.

Kong, X.-H., Deng, K., Yang, Y.-L., Zeng, Q.-D., Wang, C.: H-bond switching mediated multiple flexibility in supramolecular host-guest architectures. J. Phys. Chem. C 111, 17382–17387 (2007)CrossRef

65.

Banerjee, K., Kumar, A., Canova, F.F., Kezilebieke, S., Foster, A.S., Liljeroth, P.: Flexible self-assembled molecular templates on graphene. J. Phys. Chem. C 120, 8772–8780 (2016)CrossRef

66.

Sun, J., Zhou, X., Lei, S.: Host-guest architectures with a surface confined imine covalent organic framework as two-dimensional host networks. Chem. Comm. 52, 8691–8694 (2016)CrossRef

67.

Cui, D., MacLeod, J.M., Ebrahimi, M., Rosei, F.: Selective binding in different adsorption sites of a 2D covalent organic framework. CrystEngComm (2017)

68.

Blunt, M.O., Russell, J.C., Champness, N.R., Beton, P.H.: Templating molecular adsorption using a covalent organic framework. Chem. Comm. 46, 7157–7159 (2010)CrossRef

69.

Kittelmann, M., Nimmrich, M., Lindner, R., Gourdon, A., Kühnle, A.: Sequential and site-specific on-surface synthesis on a bulk insulator. ACS Nano 7, 5614–5620 (2013)CrossRef

70.

Lindner, R., Kühnle, A.: On-surface reactions. ChemPhysChem 16, 1582–1592 (2015)CrossRef

71.

Rastgoo-Lahrood, A., Björk, J., Lischka, M., Eichhorn, J., Kloft, S., Fritton, M., Strunskus, T., Samanta, D., Schmittel, M., Heckl, W.M., et al.: Post-synthetic decoupling of on-surface-synthesized covalent nanostructures from Ag(111). Angew. Chem. Int. Ed. 55, 7650–7654 (2016)CrossRef

72.

Rastgoo-Lahrood, A., Lischka, M., Eichhorn, J., Samanta, D., Schmittel, M., Heckl, W.M., Lackinger, M.: Reversible intercalation of iodine monolayers between on-surface synthesised covalent polyphenylene networks and Au(111). Nanoscale 9, 4995–5001 (2017)CrossRef

73.

Peyrot, D., Silly, F.: On-surface synthesis of two-dimensional covalent organic structures versus halogen-bonded self-assembly: competing formation of organic nanoarchitectures. ACS Nano 10, 5490–5498 (2016)CrossRef

Title: On-Surface Synthesis of Two-Dimensional Polymers: Rational Design and Electronic Properties
Author: Sabine Maier
Publisher: Springer International Publishing
Book: On-Surface Synthesis II
Print ISBN: 978-3-319-75809-1

Electronic ISBN: 978-3-319-75810-7

Copyright Year: 2018
DOI: https://doi.org/10.1007/978-3-319-75810-7_8

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Springer Professional "Wirtschaft"

Premium Partners