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

Aryl–Aryl Covalent Coupling on Rutile TiO2 Surfaces

verfasst von : Marek Kolmer, Jakub S. Prauzner-Bechcicki

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

In recent years, enormous progress has been made in developing bottom-up strategies based on the polymerization of specially designed building blocks directly on a supporting surface. So far, selected noble metals have been mostly used as substrates for such on-surface chemical reactions. For the sake of practical applications the semiconductor surfaces clearly represent much more attractive platforms. Especially transition metal oxides exhibiting advantageous optical as well as photo- and electrochemical properties seem to be particularly interesting. In this chapter we describe the strategies for thermally triggered on-surface covalent coupling of aryl halides performed directly on rutile titanium dioxide surfaces. We focus our work on important parameters that need to be considered for understanding and optimization of the polymerization reactions on this model transition metal oxide system.

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 Bottom-Up Fabrication of Atomically Precise Graphene Nanoribbons
Nächstes Kapitel On-Surface Synthesis of Two-Dimensional Polymers: Rational Design and Electronic Properties
Literatur
1.
Grill, L., et al.: Nano-architectures by covalent assembly of molecular building blocks. Nat. Nanotechnol. 2, 687–691 (2007)CrossRef
2.
Bieri, M., et al.: Porous graphenes: two-dimensional polymer synthesis with atomic precision. Chem. Commun. 45, 6919–6921 (2009)CrossRef
3.
Lipton-Duffin, J.A., et al.: Synthesis of polyphenylene molecular wires by surface-confined polymerization. Small 5(5), 592–597 (2009)CrossRef
4.
Perepichka, D.F., Rosei, F.: Extending polymer conjugation into the second dimension. Science 323(5911), 216–217 (2009)CrossRef
5.
Lafferentz, L., et al.: Conductance of a single conjugated polymer as a continuous function of its length. Science 323(5918), 1193–1197 (2009)CrossRef
6.
Cai, J., et al.: Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 466, 470–473 (2010)CrossRef
7.
Lafferentz, L., et al.: Controlling on-surface polymerization by hierarchical and substrate-directed growth. Nat. Chem. 4, 215–220 (2012)CrossRef
8.
Gourdon, A.: On-surface covalent coupling in ultrahigh vacuum. Angew. Chem. Int. Ed. 47, 6950–6953 (2008)CrossRef
9.
Franc, G., Gourdon, A.: Covalent networks through on-surface chemistry in ultra-high vacuum: state-of-the-art and recent developments. Phys. Chem. Chem. Phys. 13, 14283–14292 (2011)CrossRef
10.
Lindner, R., Kuhnle, A.: On-surface reactions. ChemPhysChem 16, 1582–1592 (2015)CrossRef
11.
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(8), 2484–2494 (2015)CrossRef
12.
Shen, Q., Gao, H.-Y., Fuchs, H.: Frontiers of on-surface synthesis: from principles to applications. Nano Today 13, 77–96 (2017)CrossRef
13.
Björk, J., Hanke, F., Stafström, S.: Mechanisms of halogen-based covalent self-assembly on metal surfaces. J. Am. Chem. Soc. 135(15), 5768–5775 (2013)CrossRef
14.
Treier, M., et al.: Surface-assisted cyclodehydrogenation provides a synthetic route towards easily processable and chemically tailored nanographenes. Nat. Chem. 3(1), 61–67 (2011)CrossRef
15.
Berner, N.C., et al.: Adsorption of 5,10,15,20-tetrakis (4-bromophenyl) porphyrin on germanium(001). Phys. Status Solidi C 9, 1404–1407 (2012)CrossRef
16.
Berner, N.C.: Towards stable molecular nanostructures on a semiconductor surface. School of Physics, Trinity College, University of Dublin, Dublin, Ireland (2012)
17.
Kolmer, M., et al.: Polymerization of polyanthrylene on a titanium dioxide (011)-(2×1) surface. Angew. Chem. Int. Ed. 52, 10300–10303 (2013)CrossRef
18.
Kolmer, M., et al.: On-surface polymerization on a semiconducting oxide: aryl halide coupling controlled by surface hydroxyl groups on rutile TiO2(011). Chem. Commun. 51, 11276–11279 (2015)CrossRef
19.
Vasseur, G., et al.: Pi band dispersion along conjugated organic nanowires synthesized on a metal oxide semiconductor. J. Am. Chem. Soc. 138(17), 5685–5692 (2016)CrossRef
20.
Olszowski, P., et al.: Aryl halide C–C coupling on Ge(001): H surfaces. J. Phys. Chem. C 119(49), 27478–27482 (2015)CrossRef
21.
Kittelmann, M., et al.: On-surface covalent linking of organic building blocks on a bulk insulator. ACS Nano 5, 8420–8425 (2011)CrossRef
22.
Kittelmann, M., et al.: Sequential and site-specific on-surface synthesis on a bulk insulator. ACS Nano 7(6), 5614–5620 (2013)CrossRef
23.
Bieri, 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
24.
Zebari, A.A.A., Kolmer, M., Prauzner-Bechcicki, J.S.: STM tip-assisted engineering of molecular nanostructures: PTCDA islands on Ge(001):H surfaces. Beilstein J. Nanotechnol. 4, 927–932 (2013)
25.
Zebari, A.A.A., Kolmer, M., Prauzner-Bechcicki, J.S.: Characterization of PTCDA nanocrystals on Ge(001):H-(2 × 1) surfaces. Appl. Surf. Sci. 332, 403–408 (2015)
26.
Loske, F., et al.: Growth of ordered C-60 islands on TiO2(110). Nanotechnology 20(6) (2009)
27.
Prauzner-Bechcicki, J.S., et al.: High-resolution STM studies of terephthalic acid molecules on rutile TiO2(110)-(1 × 1) surfaces. J. Phys. Chem. C 113(21), 9309–9315 (2009)CrossRef
28.
Godlewski, S., et al.: Adsorption of organic molecules on the TiO2(011) surface: STM study. J. Chem. Phys. 134(22), 224701 (2011)CrossRef
29.
Godlewski, S., et al.: Supramolecular ordering of PTCDA molecules: the key role of dispersion forces in an unusual transition from physisorbed into chemisorbed state. ACS Nano 6(10), 8536–8545 (2012)CrossRef
30.
Godlewski, S., et al.: [11]Anthrahelicene on TiO2 surfaces. Surf. Sci. 606(21–22), 1600–1607 (2012)CrossRef
31.
Grinter, D.C., et al.: Binding of a benzoate dye-molecule analogue to rutile titanium dioxide surfaces. J Phys. Chem. C 116(1), 1020–1026 (2012)CrossRef
32.
English, C.R., et al.: Formation of self-assembled monolayers of pi-conjugated molecules on TiO2 surfaces by thermal grafting of aryl and benzyl halides. Langmuir 28(17), 6866–6876 (2012)CrossRef
33.
Lanzilotto, V., et al.: Commensurate growth of densely packed PTCDI islands on the rutile TiO2(110) surface. J. Phys. Chem. C 117(24), 12639–12647 (2013)CrossRef
34.
Zając, Ł., et al.: Ordered heteromolecular overlayers formed by metal phthalocyanines and porphyrins on rutile titanium dioxide surface studied at room temperature. J. Chem. Phys. 143(22), 224702 (2015)CrossRef
35.
Godlewski, S., et al.: Transformations of PTCDA structures on rutile TiO2 induced by thermal annealing and intermolecular forces. Beilstein J. Nanotechnol. 6, 1498–1507 (2015)CrossRef
36.
Zajac, L., et al.: Self-assembling of Zn porphyrins on a (110) face of rutile TiO2–The anchoring role of carboxyl groups. Appl. Surf. Sci. 379, 277–281 (2016)CrossRef
37.
Prauzner-Bechcicki, J.S., et al.: Scanning probe microscopy studies on the adsorption of selected molecular dyes on titania. Beilstein J. Nanotechnol. 7, 1642–1653 (2016)CrossRef
38.
39.
Diebold, U.: The surface science of titanium dioxide. Surf. Sci. Rep. 48(5–8), 53–229 (2003)CrossRef
40.
Pang, C.L., Lindsay, R., Thornton, G.: Chemical reactions on rutile TiO2(110). Chem. Soc. Rev. 37(10), 2328–2353 (2008)CrossRef
41.
Dohnálek, Z., Lyubinetsky, I., Rousseau, R.: Thermally-driven processes on rutile TiO2(110)-(1 × 1): a direct view at the atomic scale. Prog. Surf. Sci. 85(5–8), 161–205 (2010)CrossRef
42.
Thomas, A.G., Syres, K.L.: Adsorption of organic molecules on rutile TiO2 and anatase TiO2 single crystal surfaces. Chem. Soc. Rev. 41(11), 4207–4217 (2012)CrossRef
43.
Godlewski, S., Szymonski, M.: Adsorption and self-assembly of large polycyclic molecules on the surfaces of TiO2 single crystals. Int. J. Mol. Sci. 14(2), 2946–2966 (2013)CrossRef
44.
Pang, C.L., Lindsay, R., Thornton, G.: Structure of clean and adsorbate-covered single-crystal rutile TiO2 surfaces. Chem. Rev. 113(6), 3887–3948 (2013)CrossRef
45.
Henderson, M.A.: A surface science perspective on photocatalysis. Surf. Sci. Rep. 66(6–7), 185–297 (2011)CrossRef
46.
Zhang, Z., Yates, J.T.: Band bending in semiconductors: chemical and physical consequences at surfaces and interfaces. Chem. Rev. 112(10), 5520–5551 (2012)CrossRef
47.
Thompson, T.L., Yates, J.T.: TiO2-based photocatalysis: surface defects, oxygen and charge transfer. Top. Catal. 35(3), 197–210 (2005)CrossRef
48.
Thompson, T.L., Yates, J.T.: Surface science studies of the photoactivation of TiO2 new photochemical processes. Chem. Rev. 106(10), 4428–4453 (2006)CrossRef
49.
Guo, Q., et al.: Elementary photocatalytic chemistry on TiO2 surfaces. Chem. Soc. Rev. 45(13), 3701–3730 (2016)CrossRef
50.
Cai, Y., Feng, Y.P.: Review on charge transfer and chemical activity of TiO2: Mechanism and applications. Prog. Surf. Sci. 91(4), 183–202 (2016)CrossRef
51.
Ramamoorthy, M., Vanderbilt, D., Kingsmith, R.D.: 1st-Principles calculations of the energetics of stoichiometric TiO2 surfaces. Phys. Rev. B 49(23), 16721–16727 (1994)CrossRef
52.
Gong, X.-Q., et al.: The 2 × 1 reconstruction of the rutile TiO2(011) surface: a combined density functional theory, X-ray diffraction, and scanning tunneling microscopy study. Surf. Sci. 603(1), 138–144 (2009)CrossRef
53.
Torrelles, X., et al.: Geometric structure of TiO2(011)-(2 × 1). Phys. Rev. Lett. 101(18), 185501 (2008)CrossRef
54.
Yurtsever, A., et al.: Imaging the TiO2(011)-(2 × 1) surface using noncontact atomic force microscopy and scanning tunneling microscopy. J. Phys. Chem. C 120(6), 3390–3395 (2016)CrossRef
55.
Pang, C.L., et al.: (2n × 1) Reconstructions of TiO2(011) revealed by noncontact atomic force microscopy and scanning tunneling microscopy. J. Phys. Chem. C 118(40), 23168–23174 (2014)CrossRef
56.
Kubo, T., Orita, H., Nozoye, H.: Surface structures of rutile TiO2(011). J. Am. Chem. Soc. 129(34), 10474–10478 (2007)CrossRef
57.
Dupont, C., et al.: Structure of TiO2(011) revealed by photoelectron diffraction. Phys. Rev. B 94(24), 241304 (2016)CrossRef
58.
Woolcot, T., et al.: Scanning tunneling microscopy contrast mechanisms for TiO2. Phys. Rev. Lett. 109(15) (2012)
59.
Wang, Q., et al.: The unexpectedly rich reconstructions of rutile TiO2(011)-(2 × 1) surface and the driving forces behind their formation: an ab initio evolutionary study. Phys. Chem. Chem. Phys. 18(29), 19549–19556 (2016)CrossRef
60.
Dulub, O., et al.: Structure, defects, and impurities at the rutile TiO2(011)-(2 × 1) surface: a scanning tunneling microscopy study. Surf. Sci. 600(19), 4407–4417 (2006)CrossRef
61.
Kolmer, M., et al.: Temperature-dependent orientation of self-organized nanopatterns on ion-irradiated TiO2(110). Phys. Rev. B 88(19), 195427 (2013)CrossRef
62.
Tao, J.G., et al.: Diffusion and reaction of hydrogen on rutile TiO2(011)-2 × 1: the role of surface structure. J. Phys. Chem. C 116(38), 20438–20446 (2012)CrossRef
63.
Li, M., et al.: The influence of the bulk reduction state on the surface structure and morphology of rutile TiO2(110) single crystals. J. Phys. Chem. B 104(20), 4944–4950 (2000)CrossRef
64.
Setvin, M., et al.: Direct view at excess electrons in TiO2 rutile and anatase. Phys. Rev. Lett. 113(8), 086402 (2014)CrossRef
65.
Deskins, N.A., Rousseau, R., Dupuis, M.: Defining the Role of Excess Electrons in the Surface Chemistry of TiO2. The Journal of Physical Chemistry C 114(13), 5891–5897 (2010)CrossRef
66.
Kowalski, P.M., et al.: Charge localization dynamics induced by oxygen vacancies on the TiO2(110) surface. Phys. Rev. Lett. 105(14), 146405 (2010)CrossRef
67.
Heckel, W., et al.: The role of hydrogen on the adsorption behavior of carboxylic acid on TiO2 surfaces. J. Phys. Chem. C 118(20), 10771–10779 (2014)CrossRef
68.
Yuan, F., et al.: The hydroxylated and reduced rutile TiO2(011)-2 × 1 surfaces: a first-principles study. Surf. Sci. 628, 126–131 (2014)CrossRef
69.
Zhang, D., Yang, M., Dong, S.: Hydroxylation of the rutile TiO2(110) surface enhancing its reducing power for photocatalysis. J. Phys. Chem. C 119(3), 1451–1456 (2014)CrossRef
70.
Zhang, Z., Yates, J.T.: A new form of chemisorbed photo- and electro-active atomic H species on the TiO2(110) surface. Surf. Sci. 652, 195–199 (2016)CrossRef
71.
Mao, X., et al.: Band-gap states of TiO2(110): major contribution from surface defects. J. Phys. Chem. Lett. 4(22), 3839–3844 (2013)CrossRef
72.
Yang, W., et al.: Controlled vacancy-assisted C–C couplings of acetaldehyde on rutile TiO2(110). J. Phys. Chem. C 118(48), 27920–27924 (2014)CrossRef
73.
Idriss, H., Barteau, M.A.: Selectivity and mechanism shifts in the reactions of acetaldehyde on oxidized and reduced TiO2(001) surfaces. Catal. Lett. 40(3), 147–153 (1996)CrossRef
74.
Benz, L., et al.: McMurry chemistry on TiO2(110): reductive C=C coupling of benzaldehyde driven by titanium interstitials. J. Am. Chem. Soc. 131(41), 15026–15031 (2009)CrossRef
75.
Benz, L., et al.: Molecular imaging of reductive coupling reactions: interstitial-mediated coupling of benzaldehyde on reduced TiO2(110). ACS Nano 5(2), 834–843 (2011)CrossRef
76.
Cremer, T., Jensen, S.C., Friend, C.M.: Enhanced photo-oxidation of formaldehyde on highly reduced o-TiO2(110). J. Phys. Chem. C 118(50), 29242–29251 (2014)CrossRef
77.
Koch, M., et al.: Voltage-dependent conductance of a single graphene nanoribbon. Nat. Nanotechnol. 7(11), 713–717 (2012)CrossRef
78.
Li, S.-C., et al.: Hydrogen bonding controls the dynamics of catechol adsorbed on a TiO2(110) surface. Science 328(5980), 882–884 (2010)CrossRef
79.
Saywell, A., et al.: Polymerization on stepped surfaces: alignment of polymers and identification of catalytic sites. Angew. Chem. Int. Ed. 51(21), 5096–5100 (2012)CrossRef
80.
Kawai, S., et al.: Quantifying the atomic-level mechanics of single long physisorbed molecular chains. Proc. Natl. Acad. Sci. U S A 111(11), 3968–3972 (2014)CrossRef
81.
Di Giovannantonio, M., et al.: Insight into organometallic intermediate and its evolution to covalent bonding in surface-confined Ullmann polymerization. ACS Nano 7(9), 8190–8198 (2013)CrossRef
82.
Miccio, L.A., et al.: Interplay between steps and oxygen vacancies on curved TiO2(110). Nano Lett. 16(3), 2017–2022 (2016)CrossRef
Metadaten
Titel
Aryl–Aryl Covalent Coupling on Rutile TiO2 Surfaces
verfasst von
Marek Kolmer
Jakub S. Prauzner-Bechcicki
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_7

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