Skip to main content
Fachgebiete
Automobil + Motoren Bauwesen + Immobilien Business IT + Informatik Elektrotechnik + Elektronik Energie + Nachhaltigkeit Finance + Banking Management + Führung Marketing + Vertrieb Maschinenbau + Werkstoffe Versicherung + Risiko
DE
EN
Bücher
Zeitschriften
Themenseiten
Organisationspsychologie Projektmanagement Marketing Smart Manufacturing
Weitere Formate
Podcasts Webinare Technik Webinare Wirtschaft Kongresse Veranstaltungskalender Awards
Jetzt Einzelzugang starten
Zugang für Unternehmen
Referenzkunden
SLX-Digitalkonferenz: Zukunftswerkstatt 2024

Mehr Umsatz mit Top-Kontakten

Am 7. Mai erfahren Sie, wie Vertriebsteams Leadgenerierung, Leadnurturing und Leadstrategien effizient steuern können.
Erweiterte Suche
Anmelden
nach oben
Erschienen in:
Mechanistic Insights into Surface-Supported Chemical Reactions Kapitel lesen Erstes Kapitel lesen

2018 | OriginalPaper | Buchkapitel

On-Surface Ullmann Reaction for the Synthesis of Polymers and Macrocycles

verfasst von : Qitang Fan, Junfa Zhu, J. Michael Gottfried

Erschienen in: On-Surface Synthesis II

Verlag: Springer International Publishing

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Compared to organic synthesis in solution, the benefits of on-surface synthesis are apparent especially when it involves insoluble reactants or when in situ characterizations of products with large molecular weight are required. This article covers the on-surface synthesis of hydrocarbon polymers and macrocycles via an Ullmann type reaction of haloarenes on metal single-crystal surfaces. The related formation of stable organometallic reaction intermediates with carbon-metal-carbon bonds is also discussed. Regarding the on-surface synthesis of polymers, deposition onto hot metal surfaces (in contrast to post-annealing) as well as high diffusion rates of the monomers lead to the increase of their chain lengths. To obtain high yields of macrocycles, it is important to enable the ring closure at the stage of the organometallic species with reversible carbon-metal-carbon bonds and to apply high-dilution conditions. In contrast, the formation of macrocycles by cyclisation of polymer chains with only covalent bonds is of low probability due to the particular mechanism of the ring-closure process in two-dimensional confinement.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

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!

Jetzt informieren

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!

Jetzt informieren

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!

Jetzt informieren
Vorheriges Kapitel Dehydrogenative and Dehalogenative Homocoupling Reactions of C–X Groups on Metal Surfaces
Nächstes Kapitel Bottom-Up Fabrication of Atomically Precise Graphene Nanoribbons
Literatur
1.
Wöhler, F.: Über künstliche Bildung des Harnstoffs. Ann. Phys. 88, 253–256 (1828)
2.
Held, P.A., Fuchs, H., Studer, A.: Covalent-bond formation via on-surface chemistry. Chem. Eur. J. 23, 5874–5892 (2017)
3.
Grave, C., Schlüter, A.D.: Shape-persistent, nano-sized macrocycles. Eur. J. Org. Chem. 3075–3098 (2002)
4.
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
5.
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
6.
Fan, Q., Wang, T., Dai, J., Kuttner, J., Hilt, G., Gottfried, J. M., Zhu, J.: On-surface pseudo-high dilution synthesis of macrocycles: principle and mechanism. ACS Nano 11, 5070–5079 (2017)
7.
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
8.
Dong, L., Liu, P.N., Lin, N.: Surface-activated coupling reactions confined on a surface. Acc. Chem. Res. 48, 2765–2774 (2015)CrossRef
9.
Ullmann, F., Meyer, G., Loewenthal, O., Gilli, E.: Symmetric biphenyl derivates. Eur. J. Org. Chem. 332, 38–81 (1904)
10.
Lipton-Duffin, J.A., Ivasenko, O., Perepichka, D.F., Rosei, F.: Synthesis of polyphenylene molecular wires by surface-confined polymerization. Small 5, 592–597 (2009)CrossRef
11.
Di Giovannantonio, M.E.G.M., Lipton-Duffin, J., Meunier, V., Cardenas, L., Fagot Revurat, Y., Cossaro, A., Verdini, A., Perepichka, D.F., Rosei, F., Contini, G.: Insight into organometallic intermediate and its evolution to covalent bonding in surface-confined Ullmann polymerization. ACS Nano 7, 8190–8198 (2013)
12.
Di Giovannantonio, M., Tomellini, M., Lipton-Duffin, J., Galeotti, G., Ebrahimi, M., Cossaro, A., Verdini, A., Kharche, N., Meunier, V., Vasseur, G., Fagot-Revurat, Y., Perepichka, D.F., Rosei, F., Contini, G.: Mechanistic picture and kinetic analysis of surface-confined Ullmann polymerization. J. Am. Chem. Soc. 138, 16696–16702 (2016)CrossRef
13.
Wang, W.H., Shi, X.Q., Wang, S.Y., Van Hove, M.A., Lin, N.: Single-molecule resolution of an organometallic intermediate in a surface-supported Ullmann coupling reaction. J. Am. Chem. Soc. 133, 13264–13267 (2011)CrossRef
14.
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
15.
Reecht, G., Bulou, H., Scheurer, F., Speisser, V., Carriere, B., Mathevet, F., Schull, G.: Oligothiophene nanorings as electron resonators for whispering gallery modes. Phys. Rev. Lett. 110, 056802 (2013)CrossRef
16.
Talirz, L., Ruffieux, P., Fasel, R.: On-surface synthesis of atomically precise graphene nanoribbons. Adv. Mater. 28, 6222–6231 (2016)CrossRef
17.
Pham, T.A., Tran, B.V., Nguyen, M.-T., Stöhr, M.: Chiral-selective formation of 1D polymers based on Ullmann-type coupling: The role of the metallic substrate. Small 13, 1603675 (2017)
18.
Ullmann, F., Bielecki, J.: Synthesis in the biphenyl series. Ber. Dtsch. Chem. Ges. 34, 2174–2185 (1901)CrossRef
19.
Xi, M., Bent, B.E.: Iodobenzene on Cu(111): formation and coupling of adsorbed phenyl groups. Surf. Sci. 278, 19–32 (1992)
20.
Xi, M., Bent, B.E.: Mechanisms of the Ullmann coupling reaction in adsorbed monolayers. J. Am. Chem. Soc. 115, 7426–7433 (1993)CrossRef
21.
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
22.
Hla, S.W., Bartels, L., Meyer, G., Rieder, K.H.: Inducing all steps of a chemical reaction with the scanning tunneling microscope tip: towards single molecule engineering. Phys. Rev. Lett. 85, 2777–2780 (2000)CrossRef
23.
Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A.P., Saleh, M., Feng, X., Müllen, K., Fasel, R.: Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466, 470–473 (2010)
24.
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
25.
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
26.
Bieri, M., Nguyen, M.T., Groning, O., Cai, J.M., Treier, M., Ait-Mansour, K., Ruffieux, P., Pignedoli, C.A., Passerone, D., Kastler, M., Müllen, K., Fasel, R.: Two-dimensional polymer formation on surfaces: insight into the roles of precursor mobility and reactivity. J. Am. Chem. Soc. 132, 16669–16676 (2010)CrossRef
27.
Fan, Q., Wang, C., Liu, L., Han, Y., Zhao, J., Zhu, J., Kuttner, J., Hilt, G., Gottfried, J.M.: Covalent, organometallic, and halogen-bonded nanomeshes from tetrabromo-terphenyl by surface-assisted synthesis on Cu(111). J. Phys. Chem. C 118, 13018–13025 (2014)CrossRef
28.
Fan, Q., Wang, T., Liu, L., Zhao, J., Zhu, J., Gottfried, J.M.: Tribromobenzene on Cu(111): temperature-dependent formation of halogen-bonded, organometallic, and covalent nanostructures. J. Chem. Phys. 142, 101906 (2015)CrossRef
29.
Klappenberger, F., Zhang, Y.-Q., Björk, J., Klyatskaya, S., Ruben, M., Barth, J.V.: On-surface synthesis of carbon-based scaffolds and nanomaterials using terminal alkynes. Acc. Chem. Res. 48, 2140–2150 (2015)CrossRef
30.
Sun, Q., Cai, L., Ding, Y., Xie, L., Zhang, C., Tan, Q., Xu, W.: Dehydrogenative homocoupling of terminal alkenes on copper surfaces: a route to dienes. Angew. Chem. Int. Ed. 54, 4549–4552 (2015)CrossRef
31.
Sun, Q., Zhang, C., Kong, H., Tan, Q., Xu, W.: On-surface aryl-aryl coupling via selective C-H activation. Chem. Commun. 50, 11825–11828 (2014)CrossRef
32.
Sun, Q., Zhang, C., Cai, L., Xie, L., Tan, Q., Xu, W.: On-surface formation of two-dimensional polymer via direct C-H activation of metal phthalocyanine. Chem. Commun. 51, 2836–2839 (2015)CrossRef
33.
He, Y., Garnica, M., Bischoff, F., Ducke, J., Bocquet, M.-L., Batzill, M., Auwärter, W., Barth, J.V.: Fusing tetrapyrroles to graphene edges by surface-assisted covalent coupling. Nat. Chem. 9, 33–38 (2017)CrossRef
34.
Zhang, H., Lin, H., Sun, K., Chen, L., Zagranyarski, Y., Aghdassi, N., Duhm, S., Li, Q., Zhong, D., Li, Y., Müllen, K., Fuchs, H., Chi, L.: On-surface synthesis of rylene-type graphene nanoribbons. J. Am. Chem. Soc. 137, 4022–4025 (2015)CrossRef
35.
Fan, Q., Wang, C., Han, Y., Zhu, J., Kuttner, J., Hilt, G., Gottfried, J.M.: Surface-assisted formation, assembly, and dynamics of planar organometallic macrocycles and zigzag shaped polymer chains with C-Cu-C bonds. ACS Nano 8, 709–718 (2014)CrossRef
36.
Chung, K.-H., Koo, B.-G., Kim, H., Yoon, J.K., Kim, J.-H., Kwon, Y.-K., Kahng, S.-J.: Electronic structures of one-dimensional metal-molecule hybrid chains studied using scanning tunneling microscopy and density functional theory. Phys. Chem. Chem. Phys. 14, 7304–7308 (2012)CrossRef
37.
Fan, Q., Dai, J., Wang, T., Kuttner, J., Hilt, G., Gottfried, J.M., Zhu, J.: Confined synthesis of organometallic chains and macrocycles by Cu–O surface templating. ACS Nano 10, 3747–3754 (2016)CrossRef
38.
Blake, M.M., Nanayakkara, S.U., Claridge, S.A., Fernandez-Torres, L.C., Sykes, E.C.H., Weiss, P.S.: Identifying reactive intermediates in the Ullmann coupling reaction by scanning tunneling microscopy and spectroscopy. J. Phys. Chem. A 113, 13167–13172 (2009)CrossRef
39.
Chung, K.-H., Kim, H., Jang, W.J., Yoon, J.K., Kahng, S.-J., Lee, J., Han, S.: Molecular multistate systems formed in two-dimensional porous networks on Ag(111). J. Phys. Chem. C 117, 302–306 (2013)CrossRef
40.
Park, J., Kim, K.Y., Chung, K.-H., Yoon, J.K., Kim, H., Han, S., Kahng, S.-J.: Interchain interactions mediated by Br adsorbates in arrays of metal-organic hybrid chains on Ag(111). J. Phys. Chem. C 115, 14834–14838 (2011)CrossRef
41.
Huang, H., Tan, Z., He, Y., Liu, J., Sun, J., Zhao, K., Zhou, Z., Tian, G., Wong, S.L., Wee, A.T.S.: Competition between hexagonal and tetragonal hexabromobenzene packing on Au(111). ACS Nano 10, 3198–3205 (2016)CrossRef
42.
Barton, D., Gao, H.-Y., Held, P.A., Studer, A., Fuchs, H., Doltsinis, N.L., Neugebauer, J.: Formation of organometallic intermediate states in on-surface Ullmann couplings. Chem. Eur. J. 23, 6190–6197 (2017)
43.
Björk, J., Hanke, F., Stafström, S.: Mechanisms of halogen-based covalent self-assembly on metal surfaces. J. Am. Chem. Soc. 135, 5768–5775 (2013)
44.
Basagni, A., Vasseur, G., Pignedoli, C.A., Vilas-Varela, M., Pena, D., Nicolas, L., Vitali, L., Lobo-Checa, J., de Oteyza, D.G., Sedona, F., Casarin, M., Ortega, J.E., Sambi, M.: Tunable band alignment with unperturbed carrier mobility of on-surface synthesized organic semiconducting wires. ACS Nano 10, 2644–2651 (2016)CrossRef
45.
Nacci, C., Ample, F., Bleger, D., Hecht, S., Joachim, C., Grill, L.: Conductance of a single flexible molecular wire composed of alternating donor and acceptor units. Nat. Commun. 6, 7397 (2015)CrossRef
46.
Lafferentz, L., Ample, F., Yu, H., Hecht, S., Joachim, C., Grill, L.: Conductance of a single conjugated polymer as a continuous function of its length. Science 323, 1193–1197 (2009)CrossRef
47.
Liu, J., Li, B.W., Tan, Y.Z., Giannakopoulos, A., Sanchez-Sanchez, C., Beljonne, D., Ruffieux, P., Fasel, R., Feng, X., Müllen, K.: Toward cove-edged low band gap graphene nanoribbons. J. Am. Chem. Soc. 137, 6097–6103 (2015)CrossRef
48.
Ruffieux, P., Wang, S., Yang, B., Sánchez-Sánchez, C., Liu, J., Dienel, T., Talirz, L., Shinde, P., Pignedoli, C.A., Passerone, D., Dumslaff, T., Feng, X., Müllen, K., Fasel, R.: On-surface synthesis of graphene nanoribbons with zigzag edge topology. Nature 531, 489–492 (2016)CrossRef
49.
Schulz, F., Jacobse, P.H., Canova, F.F., van der Lit, J., Gao, D.Z., van den Hoogenband, A., Han, P., Klein Gebbink, R.J.M., Moret, M.-E., Joensuu, P.M., Swart, I., Liljeroth, P.: Precursor geometry determines the growth mechanism in graphene nanoribbons. J. Phys. Chem. C 121, 2896–2904 (2017)CrossRef
50.
Chen, Z., Wang, H.I., Teyssandier, J., Mali, K.S., Dumslaff, T., Ivanov, I., Zhang, W., Ruffieux, P., Fasel, R., Rader, H.J., Turchinovich, D., De Feyter, S., Feng, X., Klaui, M., Narita, A., Bonn, M., Müllen, K.: Chemical vapor deposition synthesis and terahertz photoconductivity of low-bandgap n = 9 armchair graphene nanoribbons. J. Am. Chem. Soc. 139, 3635–3638 (2017)CrossRef
51.
Talirz, L., Söde, H., Dumslaff, T., Wang, S., Sanchez-Valencia, J.R., Liu, J., Shinde, P., Pignedoli, C.A., Liang, L., Meunier, V., Plumb, N.C., Shi, M., Feng, X., Narita, A., Müllen, K., Fasel, R., Ruffieux, P.: On-surface synthesis and characterization of 9-atom wide armchair graphene nanoribbons. ACS Nano 11, 1380–1388 (2017)CrossRef
52.
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
53.
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
54.
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
55.
Cai, J., Pignedoli, C.A., Talirz, L., Ruffieux, P., Sode, H., Liang, L., Meunier, V., Berger, R., Li, R., Feng, X., Müllen, K., Fasel, R.: Graphene nanoribbon heterojunctions. Nat. Nanotechnol. 9, 896–900 (2014)CrossRef
56.
Dow, A.R., Wittrig, A.M., Kenttämaa, H.I.: Laser-induced acoustic desorption mass spectrometry. Eur. J. Mass Spectrom. 18, 77–92 (2012)CrossRef
57.
Saywell, A., Magnano, G., Satterley, C.J., Perdigao, L.M., Britton, A.J., Taleb, N., del Carmen Gimenez-Lopez, M., Champness, N.R., O’Shea, J.N., Beton, P.H.: Self-assembled aggregates formed by single-molecule magnets on a gold surface. Nat. Commun. 1, 75 (2010)CrossRef
58.
Ruggli, P.: A ring with a threefold bond. Eur. J. Org. Chem. 392, 92–100 (1912)
59.
Ziegler, K., Eberle, H., Ohlinger, H.: Polynomial Ring Systems I. The preparative, productive synthesis of polymethyl ketones with more than 6 mmbers of the ring. Eur. J. Org. Chem. 504, 94–130 (1933)
60.
Jia, Z., Monteiro, M.J.: Synthesis of cyclic polymers via ring closure. Adv. Polym. Sci. 262, 295–327 (2013)CrossRef
61.
Melson G.A., Bush D.H.: Cyclic tetramerisation of o-aminobenzaldehyde in presence of metal ions. Proc. chem. Soc. 223 (1963)
62.
Laughrey, Z.R., Gibb, B.C.: Macrocycle synthesis through templation. In: Schalley, C.A., Vögtle, F., Dötz, K.H. (eds.) Templates in Chemistry II vol. 249, pp. 67–125 (2005)
63.
Hoffmann, M., Wilson, C.J., Odell, B., Anderson, H.L.: Template-directed synthesis of a pi-conjugated porphyrin nanoring. Angew. Chem. Int. Ed. 46, 3122–3125 (2007)CrossRef
64.
Sprafke, J.K., Kondratuk, D.V., Wykes, M., Thompson, A.L., Hoffmann, M., Drevinskas, R., Chen, W.H., Yong, C.K., Karnbratt, J., Bullock, J.E., Malfois, M., Wasielewski, M.R., Albinsson, B., Herz, L.M., Zigmantas, D., Beljonne, D., Anderson, H.L.: Belt-shaped pi-systems: relating geometry to electronic structure in a six-porphyrin nanoring. J. Am. Chem. Soc. 133, 17262–17273 (2011)CrossRef
65.
Svatek, S.A., Perdigao, L.M., Stannard, A., Wieland, M.B., Kondratuk, D.V., Anderson, H.L., O’Shea, J.N., Beton, P.H.: Mechanical stiffening of porphyrin nanorings through supramolecular columnar stacking. Nano Lett. 13, 3391–3395 (2013)CrossRef
66.
O’Sullivan, M.C., Sprafke, J.K., Kondratuk, D.V., Rinfray, C., Claridge, T.D., Saywell, A., Blunt, M.O., O’Shea, J.N., Beton, P.H., Malfois, M., Anderson, H.L.: Vernier templating and synthesis of a 12-porphyrin nano-ring. Nature 469, 72–75 (2011)CrossRef
67.
Anderson, S., Anderson, H.L.: Templates in organic synthesis: definitions and roles. Templated organic synthesis, pp. 1–38. Wiley-VCH Verlag GmbH (2007)
68.
Lin, N., Stepanow, S., Ruben, M., Barth, J.V.: Surface-confined supramolecular coordination chemistry. In: Broekmann, P., Dötz, K.H., Schalley, C.A. (eds.) Templates in Chemistry III, Topics in Current Chemistry, pp. 1–44 (2009)
69.
Chen, M., Feng, X., Zhang, L., Ju, H., Xu, Q., Zhu, J., Gottfried, J.M., Ibrahim, K., Qian, H., Wang, J.: Direct synthesis of nickel(II) tetraphenylporphyrin and its interaction with a Au(111) surface: a comprehensive study. J. Phys. Chem. C 114, 9908–9916 (2010)CrossRef
70.
Gottfried, J.M.: Surface chemistry of porphyrins and phthalocyanines. Sur. Sci. Rep. 70, 259–379 (2015)CrossRef
71.
Weckesser, J., De Vita, A., Barth, J.V., Cai, C., Kern, K.: Mesoscopic correlation of supramolecular chirality in one-dimensional hydrogen-bonded assemblies. Phys. Rev. Lett. 87, 096101 (2001)CrossRef
72.
Gambardella, P., Stepanow, S., Dmitriev, A., Honolka, J., de Groot, F.M.F., Lingenfelder, M., Sen Gupta, S., Sarma, D.D., Bencok, P., Stanescu, S., Clair, S., Pons, S., Lin, N., Seitsonen, A.P., Brune, H., Barth, J.V., Kern, K.: Supramolecular control of the magnetic anisotropy in two-dimensional high-spin Fe arrays at a metal interface. Nat. Mater. 8, 189–193 (2009)
73.
Barth, J.V., Costantini, G., Kern, K.: Engineering atomic and molecular nanostructures at surfaces. Nature 437, 671–679 (2005)CrossRef
74.
Shi, Z., Lin, N.: Porphyrin-based two-dimensional coordination kagome lattice self-assembled on a Au(111) surface. J. Am. Chem. Soc. 131, 5376–5377 (2009)CrossRef
75.
Shi, Z., Lin, N.: Structural and chemical control in assembly of multicomponent metal-organic coordination networks on a surface. J. Am. Chem. Soc. 132, 10756–10761 (2010)CrossRef
76.
Lin, T., Shang, X.S., Adisoejoso, J., Liu, P.N., Lin, N.: Steering on-surface polymerization with metal-directed template. J. Am. Chem. Soc. 135, 3576–3582 (2013)CrossRef
77.
Dai, J., Fan, Q., Wang, T., Kuttner, J., Hilt, G., Gottfried, J.M., Zhu, J.: The role of the substrate structure in the on-surface synthesis of organometallic and covalent oligophenylene chains. Phys. Chem. Chem. Phys. 18, 20627–20634 (2016)CrossRef
78.
Jacobson, H., Beckmann, C.O., Stockmayer, W.H.: Intramolecular reaction in polycondensations. 2. Ring-chain equilibrium in polydecamethylene adipate. J. Chem. Phys. 18, 1607–1612 (1950)CrossRef
79.
Jacobson, H., Stockmayer, W.H.: Intramolecular reaction in polycondensations. 1. The theory of linear systems. J. Chem. Phys. 18, 1600–1606 (1950)CrossRef
80.
Müllegger, S., Salzmann, I., Resel, R., Hlawacek, G., Teichert, C., Winkler, A.: Growth kinetics, structure, and morphology of para-quaterphenyl thin films on gold(111). J. Chem. Phys. 121, 2272–2277 (2004)CrossRef
Metadaten
Titel
On-Surface Ullmann Reaction for the Synthesis of Polymers and Macrocycles
verfasst von
Qitang Fan
Junfa Zhu
J. Michael Gottfried
Copyright-Jahr
2018
Buch
On-Surface Synthesis II

Print ISBN: 978-3-319-75809-1

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

Copyright-Jahr: 2018

DOI
https://doi.org/10.1007/978-3-319-75810-7_5

Premium Partner

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen. 

    Zur Marktübersicht
    Bildnachweise