Abstract
On-surface synthesis has become a very promising bottom-up approach to obtain a functional surface with designable chemical structures. Dynamic covalent chemistry is an interesting reaction strategy to form thermodynamically controlled products utilizing the reversible covalent bond as linkage, which can be formed, broken, and reformed during the reaction and therefore provide an incidence of error-checking and self-healing. In this chapter, we focused on the surface-assisted synthesis of molecular nanostructures using dynamic covalent linkers. By proper tuning the on-surface dynamic covalent reaction processes, highly ordered covalent bond connected nanostructures can be obtained on surfaces.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Zhang, X., Chen, T., Yan, H.-J., Wang, D., Fan, Q.-H., Wan, L.-J., Ghosh, K., Yang, H.-B., Stang, P.J.: Engineering of linear molecular nanostructures by a hydrogen-bond-mediated modular and flexible Host−Guest assembly. ACS Nano 4(10), 5685–5692 (2010)
Gourdon, A.: On-surface covalent coupling in ultrahigh vacuum. Angew. Chem. Int. Ed. 47(37), 6950–6953 (2008)
Lin, T., Shang, X.S., Liu, P.N., Lin, N.: Multicomponent assembly of supramolecular coordination polygons on a Au(111) surface. J. Phys. Chem. C 117(44), 23027–23033 (2013)
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(17), 4668–4672 (2013)
Liu, J., Ruffieux, P., Feng, X., Mullen, K., Fasel, R.: Cyclotrimerization of arylalkynes on Au(111). Chem. Commun. 50(76), 11200–11203 (2014)
Lewis, E.A., Murphy, C.J., Liriano, M.L., Sykes, E.C.H.: Atomic-scale insight into the formation, mobility and reaction of Ullmann coupling intermediates. Chem. Commun. 50(8), 1006–1008 (2014)
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(57), 7680–7682 (2014)
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(1), 709–718 (2013)
Lipton-Duffin, J.A., Miwa, J.A., Kondratenko, M., Cicoira, F., Sumpter, B.G., Meunier, V., Perepichka, D.F., Rosei, F.: Step-by-step growth of epitaxially aligned polythiophene by surface-confined reaction. Proc. Natl. Acad. Sci. USA 107(25), 11200–11204 (2010)
Schlutter, F., Rossel, F., Kivala, M., Enkelmann, V., Gisselbrecht, J.P., Ruffieux, P., Fasel, R., Mullen, K.: Pi-conjugated heterotriangulene macrocycles by solution and surface-supported synthesis toward honeycomb networks. J. Am. Chem. Soc. 135(11), 4550–4557 (2013)
Mendez, J., Lopez, M.F., Martin-Gago, J.A.: On-surface synthesis of cyclic organic molecules. Chem. Soc. Rev. 40(9), 4578–4590 (2011)
Zhang, X., Zeng, Q., Wang, C.: On-surface single molecule synthesis chemistry, a promising bottom-up approach towards functional surfaces. Nanoscale 5(18), 8269–8287 (2013)
El Garah, M., MacLeod, J.M., Rosei, F.: Covalently bonded networks through surface-confined polymerization. Surf. Sci. 613, 6–14 (2013)
Liu, X.-H., Guan, C.-Z., Wang, D., Wan, L.-J.: Graphene-like single-layered covalent organic frameworks, synthesis strategies and application prospects. Adv. Mater. 26(40), 6912–6920 (2014)
Rowan, S.J., Cantrill, S.J., Cousins, G.R.L., Sanders, J.K.M., Stoddart, J.F.: Dynamic covalent chemistry. Angew. Chem. Int. Ed. 41(6), 898–952 (2002)
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(5751), 1166–1170 (2005)
Weigelt, S., Busse, C., Bombis, C., Knudsen, M.M., Gothelf, K.V., Strunskus, T., Wöll, C., Dahlbom, M., Hammer, B., Lægsgaard, E., Besenbacher, F., Linderoth, T.R.: Covalent interlinking of an aldehyde and an amine on a Au(111) surface in ultrahigh vacuum. Angew. Chem. 119(48), 9387–9390 (2007)
Dienstmaier, J.F., Gigler, A.M., Goetz, A.J., Knochel, P., Bein, T., Lyapin, A., Reichlmaier, S., Heckl, W.M., Lackinger, M.: Synthesis of well-ordered COF monolayers: surface growth of nanocrystalline precursors versus direct on-surface polycondensation. ACS Nano 5(12), 9737–9745 (2011)
Dienstmaier, J.F., Medina, D.D., Dogru, M., Knochel, P., Bein, T., Heckl, W.M., Lackinger, M.: Isoreticular two-dimensional covalent organic frameworks synthesized by on-surface condensation of diboronic acids. ACS Nano 6(8), 7234–7242 (2012)
Guan, C.-Z., Wang, D., Wan, L.-J.: Construction and repair of highly ordered 2D covalent networks by chemical equilibrium regulation. Chem. Commun. 48(24), 2943–2945 (2012)
Faury, T., Clair, S., Abel, M., Dumur, F., Gigmes, D., Porte, L.: Sequential linking to control growth of a surface covalent organic framework. J. Phys. Chem. C 116(7), 4819–4823 (2012)
Acharyya, K., Mukherjee, S., Mukherjee, P.S.: Molecular marriage through partner preferences in covalent cage formation and cage-to-cage transformation. J. Am. Chem. Soc. 135(2), 554–557 (2013)
Jin, Y., Zhu, Y., Zhang, W.: Development of organic porous materials through schiff-base chemistry. Cryst. Eng. Comm. G 15, 1484–1499 (2013)
Weigelt, S., Busse, C., Bombis, C., Knudsen, M.M., Gothelf, K.V., Lægsgaard, E., Besembacher, F., Linderoth, T.R.: Surface synthesis of 2D branched polymer nanostructures. Angew. Chem. Int. Ed. 47(23), 4406–4410 (2008)
Ciesielski, A., El Garah, M., Haar, S., Kovaricek, P., Lehn, J.M., Samori, P.: Dynamic covalent chemistry of bisimines at the solid/liquid interface monitored by scanning tunnelling microscopy. Nat. Chem. 6(11), 1017–1023 (2014)
Li, Y., Wan, J., Deng, K., Han, X., Lei, S., Yang, Y., Zheng, Q., Zeng, Q., Wang, C.: Transformation of self-assembled structure by the addition of active reactant. J. Phys. Chem. C 115(14), 6540–6544 (2011)
Hu, F.-Y., Zhang, X.-M., Wang, X.-C., Wang, S., Wang, H.-Q., Duan, W.-B., Zeng, Q.-D., Wang, C.: In Situ STM investigation of two-dimensional chiral assemblies through schiff-base condensation at a liquid/solid interface. ACS Appl. Mater. Interfaces 5(5), 1583–1587 (2013)
Liu, X.-H., Wang, D., Wan, L.-J.: Surface tectonics of nanoporous networks of melamine-capped molecular building blocks formed through interface schiff-base reactions. Chem. Asian J. 8(10), 2466–2470 (2013)
Tanoue, R., Higuchi, R., Enoki, N., Miyasato, Y., Uemura, S., Kimizuka, N., Stieg, A.Z., Gimzewski, J.K., Kunitake, M.: Thermodynamically controlled self-assembly of covalent nanoarchitectures in aqueous solution. ACS Nano 5(5), 3923–3929 (2011)
Liu, X.-H., Guan, C.-Z., Ding, S.-Y., Wang, W., Yan, H.-J., Wang, D., Wan, L.-J.: On-surface synthesis of single-layered two-dimensional covalent organic frameworks via solid-vapor interface reactions. J. Am. Chem. Soc. 135(28), 10470–10474 (2013)
Liu, X.-H., Mo, Y.-P., Yue, J.-Y., Zheng, Q.-N., Yan, H.-J., Wang, D., Wan, L.-J.: Isomeric routes to schiff-base single-layered covalent organic frameworks. Small 10(23), 4934–4939 (2014)
Xu, L., Zhou, X., Yu, Y., Tian, W.Q., Ma, J., Lei, S.: Surface-confined crystalline two-dimensional covalent organic frameworks via on-surface schiff-base coupling. ACS Nano 7(9), 8066–8073 (2013)
Xu, L., Zhou, X., Tian, W.Q., Gao, T., Zhang, Y.F., Lei, S., Liu, Z.F.: Surface-confined single-layer covalent organic framework on single-layer graphene grown on copper foil. Angew. Chem. Int. Ed. 53(36), 9564–9568 (2014)
Schmitz, C.H., Ikonomov, J., Sokolowski, M.: Two-dimensional polyamide networks with a broad pore size distribution on the Ag(111) surface. J. Phys. Chem. C 115(15), 7270–7278 (2011)
Jensen, S., Greenwood, Früchtl H.A., Baddeley, C.J.: STM investigation on the formation of oligoamides on Au(111) by surface-confined reactions of melamine with trimesoyl chloride. J. Phys. Chem. C 115(17), 8630–8636 (2011)
Treier, M., Fasel, R., Champness, N.R., Argent, S., Richardson, N.V.: Molecular imaging of polyimide formation. Phys. Chem. Chem. Phys. 11(8), 1209–1214 (2009)
Treier, M., Richardson, N.V., Fasel, R.: Fabrication of surface-supported low-dimensional polyimide networks. J. Am. Chem. Soc. 130(43), 14054–14055 (2008)
Marele, A.C., Mas-Balleste, R., Terracciano, L., Rodriguez-Fernandez, J., Berlanga, I., Alexandre, S.S., Otero, R., Gallego, J.M., Zamora, F., Gomez-Rodriguez, J.M.: Formation of a surface covalent organic framework based on polyester condensation. Chem. Commun. 48(54), 6779–6781 (2012)
Greenwood, J., Früchtl, H.A., Baddeley, C.J.: Surface-confined reaction of aliphatic diamines with aromatic diisocyanates on Au(111) leads to ordered oligomer assemblies. J. Phys. Chem. C 117(9), 4515–4520 (2013)
Wan, S., Guo, J., Kim, J., Ihee, H., Jiang, D.: A belt-shaped, blue luminescent, and semiconducting covalent organic framework. Angew. Chem. Int. Ed. 48(18), 3207 (2009)
Baughman, R.H., Eckhardt, H., Kertesz, M.: Structure-property predictions for new planar forms of carbon: Layered phases containing sp 2 and sp atoms. J. Chem. Phys. 87(11), 6687–6699 (1987)
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this paper
Cite this paper
Yue, JY., Wan, LJ., Wang, D. (2016). On-Surface Dynamic Covalent Chemistry. In: Gourdon, A. (eds) On-Surface Synthesis. Advances in Atom and Single Molecule Machines. Springer, Cham. https://doi.org/10.1007/978-3-319-26600-8_11
Download citation
DOI: https://doi.org/10.1007/978-3-319-26600-8_11
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-26598-8
Online ISBN: 978-3-319-26600-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)