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2020 | OriginalPaper | Buchkapitel

Chemical Anchoring of Molecular Rotors

verfasst von : Oumaima Aiboudi, Franziska Lissel

Erschienen in: Building and Probing Small for Mechanics

Verlag: Springer International Publishing

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Abstract

A reliable anchoring on the substrate is the fundamental prerequisite to investigate surface-bound molecular rotors. The choice of the anchor group is dependent on the used substrate, and the surface-molecule bond must be sufficiently strong to endure under electrical operation. Here, we give an overview of anchor groups suitable to immobilize molecules on gold and other coinage metals via chemisorption. Sulfur-, nitrogen- and oxygen-based anchors are reviewed, N-heterocyclic carbenes as well as selected examples of other carbon-based anchors are considered, and examples of anchor groups reported for surface-bound molecular rotors are given. Anchoring is discussed in terms of the surface-molecule binding mode, i.e. radical adsorption and lone pair interaction. Green’s ligand classification, Pearson’s hard/soft- acid/base (HSAB) principle as well as the concepts denticity and podality are considered. Emphasis is placed on chemical aspects, e.g. the need to protect and controllably deprotect reactive anchors such as thiols and acetylenes.

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Literatur
1.
Zurück zum Zitat Fletcher, S.P., Dumur, F., Pollard, M.M., Feringa, B.L.: Chemistry: a reversible, unidirectional molecular rotary motor driven by chemical energy. Science 310(5745), 80–82 (2005) Fletcher, S.P., Dumur, F., Pollard, M.M., Feringa, B.L.: Chemistry: a reversible, unidirectional molecular rotary motor driven by chemical energy. Science 310(5745), 80–82 (2005)
2.
Zurück zum Zitat Kulago, A.A., Mes, E.M., Klok, M., Meetsma, A., Brouwer, A.M., Feringa, B.L.: Ultrafast light-driven nanomotors based on an acridane stator. J. Org. Chem. 75(3), 666–679 (2010)PubMed Kulago, A.A., Mes, E.M., Klok, M., Meetsma, A., Brouwer, A.M., Feringa, B.L.: Ultrafast light-driven nanomotors based on an acridane stator. J. Org. Chem. 75(3), 666–679 (2010)PubMed
3.
Zurück zum Zitat Manzano, C., et al.: Step-by-step rotation of a molecule-gear mounted on an atomic-scale axis. Nat. Mater. 8(7), 576–579 (2009)PubMed Manzano, C., et al.: Step-by-step rotation of a molecule-gear mounted on an atomic-scale axis. Nat. Mater. 8(7), 576–579 (2009)PubMed
4.
Zurück zum Zitat Molecular gears: wheels in motion. NPG Asia Mater. 1(1), 13 (2009) Molecular gears: wheels in motion. NPG Asia Mater. 1(1), 13 (2009)
5.
Zurück zum Zitat Stipe, B.C., Rezaei, M.A., Ho, W.: Inducing and viewing the rotational motion of a single molecule. Science 279(5358), 1907–1909 (1998) Stipe, B.C., Rezaei, M.A., Ho, W.: Inducing and viewing the rotational motion of a single molecule. Science 279(5358), 1907–1909 (1998)
6.
Zurück zum Zitat Gimzewski, J.K., Joachim, C., Schlittler, R.R., Langlais, V., Tang, H., Johannsen, I.: Rotation of a single molecule within a supramolecular bearing. Science 281(5376), 531–533 (1998) Gimzewski, J.K., Joachim, C., Schlittler, R.R., Langlais, V., Tang, H., Johannsen, I.: Rotation of a single molecule within a supramolecular bearing. Science 281(5376), 531–533 (1998)
7.
Zurück zum Zitat Zheng, X., Mulcahy, M.E., Horinek, D., Galeotti, F., Magnera, T.F., Michl, J.: Dipolar and nonpolar altitudinal molecular rotors mounted on an Au(111) surface. J. Am. Chem. Soc. 126(14), 4540–4542 (2004)PubMed Zheng, X., Mulcahy, M.E., Horinek, D., Galeotti, F., Magnera, T.F., Michl, J.: Dipolar and nonpolar altitudinal molecular rotors mounted on an Au(111) surface. J. Am. Chem. Soc. 126(14), 4540–4542 (2004)PubMed
8.
Zurück zum Zitat Kottas, G.S., Clarke, L.I., Horinek, D., Michl, J.: Artificial molecular rotors. Chem. Rev 105(4), 1281–1376 (2005) Kottas, G.S., Clarke, L.I., Horinek, D., Michl, J.: Artificial molecular rotors. Chem. Rev 105(4), 1281–1376 (2005)
9.
Zurück zum Zitat Xue, M., Wang, K.L.: Molecular rotors as switches. Sensors (Switzerland) 12(9), 11612–11637 (2012) Xue, M., Wang, K.L.: Molecular rotors as switches. Sensors (Switzerland) 12(9), 11612–11637 (2012)
10.
Zurück zum Zitat Perera, U.G.E., et al.: Controlled clockwise and anticlockwise rotational switching of a molecular motor. Nat. Nanotechnol. 8(1), 46–51 (2013)PubMed Perera, U.G.E., et al.: Controlled clockwise and anticlockwise rotational switching of a molecular motor. Nat. Nanotechnol. 8(1), 46–51 (2013)PubMed
11.
Zurück zum Zitat Carroll, G.T., Pollard, M.M., van Delden, R., Feringa, B.L.: Controlled rotary motion of light-driven molecular motors assembled on a gold film. Chem. Sci. 1(1), 97–101 (2010) Carroll, G.T., Pollard, M.M., van Delden, R., Feringa, B.L.: Controlled rotary motion of light-driven molecular motors assembled on a gold film. Chem. Sci. 1(1), 97–101 (2010)
12.
Zurück zum Zitat Carroll, G.T., London, G., Landaluce, T.F., Rudolf, P., Feringa, B.L.: Adhesion of photon-driven molecular motors to surfaces via 1, 3-dipolar cycloadditions: effect of interfacial interactions on molecular motion. ACS Nano 5(1), 622–630 (2011)PubMed Carroll, G.T., London, G., Landaluce, T.F., Rudolf, P., Feringa, B.L.: Adhesion of photon-driven molecular motors to surfaces via 1, 3-dipolar cycloadditions: effect of interfacial interactions on molecular motion. ACS Nano 5(1), 622–630 (2011)PubMed
13.
Zurück zum Zitat Stipe, B.C., Rezaei, M.A., Ho, W. Inducing and viewing the rotational motion of a single molecule. Science 279(5358), 1907–1909 (1998) Stipe, B.C., Rezaei, M.A., Ho, W. Inducing and viewing the rotational motion of a single molecule. Science 279(5358), 1907–1909 (1998)
14.
Zurück zum Zitat Ulman, A.: Formation and structure of self-assembled monolayers. Chem. Rev. 96(4), 1533–1554 (1996)PubMed Ulman, A.: Formation and structure of self-assembled monolayers. Chem. Rev. 96(4), 1533–1554 (1996)PubMed
15.
Zurück zum Zitat Rao, B.V., Kwon, K.Y., Liu, A., Bartels, L.: 2, 5-dichlorothiophenol on Cu(111): initial adsorption site and scanning tunnel microscope-based abstraction of hydrogen at high intramolecular selectivity. J. Chem. Phys. 119(20), 10879–10884 (2003) Rao, B.V., Kwon, K.Y., Liu, A., Bartels, L.: 2, 5-dichlorothiophenol on Cu(111): initial adsorption site and scanning tunnel microscope-based abstraction of hydrogen at high intramolecular selectivity. J. Chem. Phys. 119(20), 10879–10884 (2003)
16.
Zurück zum Zitat Lippert, E.: The strengths of chemical bonds, von T.L. Cottrell. Butterworths Publications Ltd., London 1958. 2. Aufl., X, 317 S., geb.t—/32/—. Angew. Chemie 72(16), 602–602 (1960) Lippert, E.: The strengths of chemical bonds, von T.L. Cottrell. Butterworths Publications Ltd., London 1958. 2. Aufl., X, 317 S., geb.t—/32/—. Angew. Chemie 72(16), 602–602 (1960)
17.
Zurück zum Zitat Pensa, E., et al.: The chemistry of the sulfur-gold interface: in search of a unified model. Acc. Chem. Res. 45(8), 1183–1192 (2012)PubMed Pensa, E., et al.: The chemistry of the sulfur-gold interface: in search of a unified model. Acc. Chem. Res. 45(8), 1183–1192 (2012)PubMed
18.
Zurück zum Zitat Vericat, C., et al.: Self-assembled monolayers of thiolates on metals: a review article on sulfur-metal chemistry and surface structures. RSC Advances 4(53), 27730–27754 (2014). Royal Society of Chemistry Vericat, C., et al.: Self-assembled monolayers of thiolates on metals: a review article on sulfur-metal chemistry and surface structures. RSC Advances 4(53), 27730–27754 (2014). Royal Society of Chemistry
19.
Zurück zum Zitat Valášek, M., Lindner, M., Mayor, M.: Rigid multipodal platforms for metal surfaces. Beilstein J. Nanotechnol. 7(1), 374–405 (2016). Beilstein-Institut Zur Forderung der Chemischen Wissenschaften Valášek, M., Lindner, M., Mayor, M.: Rigid multipodal platforms for metal surfaces. Beilstein J. Nanotechnol. 7(1), 374–405 (2016). Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
20.
Zurück zum Zitat Kitagawa, T., et al.: Rigid molecular tripod with an adamantane framework and thiol legs. Synthesis and observation of an ordered monolayer on Au(111). J. Org. Chem. 71(4), 1362–1369 (2006)PubMed Kitagawa, T., et al.: Rigid molecular tripod with an adamantane framework and thiol legs. Synthesis and observation of an ordered monolayer on Au(111). J. Org. Chem. 71(4), 1362–1369 (2006)PubMed
21.
Zurück zum Zitat Green, M.L.H.: A new approach to the formal classification of covalent compounds of the elements. J. Organomet. Chem. (1995) Green, M.L.H.: A new approach to the formal classification of covalent compounds of the elements. J. Organomet. Chem. (1995)
22.
Zurück zum Zitat Haaland, A.: Covalent versus dative bonds to main group metals, a useful distinction. Angew. Chemie Int. Ed. English 28(8), 992–1007 (1989) Haaland, A.: Covalent versus dative bonds to main group metals, a useful distinction. Angew. Chemie Int. Ed. English 28(8), 992–1007 (1989)
23.
Zurück zum Zitat Pearson, R.G.: Hard and soft Acids and bases. J. Am. Chem. Soc. 85(22), 3533–3539 (1963) Pearson, R.G.: Hard and soft Acids and bases. J. Am. Chem. Soc. 85(22), 3533–3539 (1963)
25.
Zurück zum Zitat Patrone, L., Palacin, S., Bourgoin, J.P., Lagoute, J., Zambelli, T., Gauthier, S.: Direct comparison of the electronic coupling efficiency of sulfur and selenium anchoring groups for molecules adsorbed onto gold electrodes. Chem. Phys. 281(2–3), 325–332 (2002) Patrone, L., Palacin, S., Bourgoin, J.P., Lagoute, J., Zambelli, T., Gauthier, S.: Direct comparison of the electronic coupling efficiency of sulfur and selenium anchoring groups for molecules adsorbed onto gold electrodes. Chem. Phys. 281(2–3), 325–332 (2002)
26.
Zurück zum Zitat Lissel, F., et al.: Organometallic single-molecule electronics: tuning electron transport through X(diphosphine)2FeC4Fe(diphosphine)2X building blocks by varying the Fe-X-Au anchoring scheme from coordinative to covalent. J. Am. Chem. Soc. 136(41), 14560–14569 (2014)PubMed Lissel, F., et al.: Organometallic single-molecule electronics: tuning electron transport through X(diphosphine)2FeC4Fe(diphosphine)2X building blocks by varying the Fe-X-Au anchoring scheme from coordinative to covalent. J. Am. Chem. Soc. 136(41), 14560–14569 (2014)PubMed
27.
Zurück zum Zitat Grönbeck, H., Curioni, A., Andreoni, W.: Thiols and disulfides on the Au(111) surface: the headgroup-gold interaction. J. Am. Chem. Soc. 122(16), 3839–3842 (2000) Grönbeck, H., Curioni, A., Andreoni, W.: Thiols and disulfides on the Au(111) surface: the headgroup-gold interaction. J. Am. Chem. Soc. 122(16), 3839–3842 (2000)
28.
Zurück zum Zitat Reed, M.A., Zhou, C., Muller, C.J., Burgin, T.P., Tour, J. M.: Conductance of a molecular junction. Science 278(5336), 252–254 (1997) Reed, M.A., Zhou, C., Muller, C.J., Burgin, T.P., Tour, J. M.: Conductance of a molecular junction. Science 278(5336), 252–254 (1997)
29.
Zurück zum Zitat Schwarz, F., et al.: High-conductive organometallic molecular wires with delocalized electron systems strongly coupled to metal electrodes. (2014) Schwarz, F., et al.: High-conductive organometallic molecular wires with delocalized electron systems strongly coupled to metal electrodes. (2014)
30.
Zurück zum Zitat Yaliraki, S.N., Kemp, M., Ratner, M.A.: Conductance of molecular wires: influence of molecule-electrode binding. J. Am. Chem. Soc. 121(14), 3428–3434 (1999) Yaliraki, S.N., Kemp, M., Ratner, M.A.: Conductance of molecular wires: influence of molecule-electrode binding. J. Am. Chem. Soc. 121(14), 3428–3434 (1999)
31.
Zurück zum Zitat Valkenier, H., Huisman, E.H., van Hal, P.A., de Leeuw, D.M., Chiechi, R.C., Hummelen, J.C.: Formation of high-quality self-assembled monolayers of conjugated dithiols on gold: base matters. J. Am. Chem. Soc. 133(13), 4930–4939 (2011)PubMed Valkenier, H., Huisman, E.H., van Hal, P.A., de Leeuw, D.M., Chiechi, R.C., Hummelen, J.C.: Formation of high-quality self-assembled monolayers of conjugated dithiols on gold: base matters. J. Am. Chem. Soc. 133(13), 4930–4939 (2011)PubMed
32.
Zurück zum Zitat Tielens, F., Santos, E.: AuS and SH bond formation/breaking during the formation of alkanethiol SAMs on Au(111): a theoretical study. J. Phys. Chem. C 114(20), 9444–9452 (2010) Tielens, F., Santos, E.: AuS and SH bond formation/breaking during the formation of alkanethiol SAMs on Au(111): a theoretical study. J. Phys. Chem. C 114(20), 9444–9452 (2010)
33.
Zurück zum Zitat Whetten, R.L., Price, R.C.: Chemistry: nano-golden order. Science 318(5849), 407–408 (2007). American Association for the Advancement of Science Whetten, R.L., Price, R.C.: Chemistry: nano-golden order. Science 318(5849), 407–408 (2007). American Association for the Advancement of Science
34.
Zurück zum Zitat Lukkari, J., et al.: Organic thiosulfates (bunte salts): novel surface-active sulfur compounds for the preparation of self-assembled monolayers on gold. Langmuir 15(10), 3529–3537 (1999) Lukkari, J., et al.: Organic thiosulfates (bunte salts): novel surface-active sulfur compounds for the preparation of self-assembled monolayers on gold. Langmuir 15(10), 3529–3537 (1999)
35.
Zurück zum Zitat Niebel, C., Calard, F., Jarrosson, T., Lère-Porte, J.P., Breton, T., Serein-Spirau, F.: Spontaneous assembly of silylethane-thiol derivatives on Au(111): a chemically robust thiol protecting group as the precursor for the direct formation of aromatic gold thiolate monolayers. Chem. Commun. 51(36), 7622–7625 (2015) Niebel, C., Calard, F., Jarrosson, T., Lère-Porte, J.P., Breton, T., Serein-Spirau, F.: Spontaneous assembly of silylethane-thiol derivatives on Au(111): a chemically robust thiol protecting group as the precursor for the direct formation of aromatic gold thiolate monolayers. Chem. Commun. 51(36), 7622–7625 (2015)
36.
Zurück zum Zitat Cai, L., Yao, Y., Yang, J., Price, D.W., Tour, J.M.: Chemical and potential-assisted assembly of thiolacetyl-terminated oligo(phenylene ethynylene)s on gold surfaces. Chem. Mater. 14(7), 2905–2909 (2002) Cai, L., Yao, Y., Yang, J., Price, D.W., Tour, J.M.: Chemical and potential-assisted assembly of thiolacetyl-terminated oligo(phenylene ethynylene)s on gold surfaces. Chem. Mater. 14(7), 2905–2909 (2002)
37.
Zurück zum Zitat Béthencourt, M.I., Srisombat, L.O., Chinwangso, P., Lee, T.R.: SAMs on gold derived from the direct adsorption of alkanethioacetates are inferior to those derived from the direct adsorption of alkanethiols. Langmuir 25(3), 1265–1271 (2009)PubMed Béthencourt, M.I., Srisombat, L.O., Chinwangso, P., Lee, T.R.: SAMs on gold derived from the direct adsorption of alkanethioacetates are inferior to those derived from the direct adsorption of alkanethiols. Langmuir 25(3), 1265–1271 (2009)PubMed
38.
Zurück zum Zitat Tour, J.M., et al.: Self-assembled monolayers and multilayers of conjugated thiols, α, ω-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces. J. Am. Chem. Soc. 117(37), 9529–9534 (1995) Tour, J.M., et al.: Self-assembled monolayers and multilayers of conjugated thiols, α, ω-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces. J. Am. Chem. Soc. 117(37), 9529–9534 (1995)
39.
Zurück zum Zitat Biebuyck, H.A., Bain, C.D., Whitesides, G.M.: Comparison of organic monolayers on polycrystalline gold spontaneously assembled from solutions containing dialkyl disulfides or alkanethiols. Langmuir 10(6), 1825–1831 (1994) Biebuyck, H.A., Bain, C.D., Whitesides, G.M.: Comparison of organic monolayers on polycrystalline gold spontaneously assembled from solutions containing dialkyl disulfides or alkanethiols. Langmuir 10(6), 1825–1831 (1994)
40.
Zurück zum Zitat Hagenhoff, B., Benninghoven, A., Spinke, J., Liley, M., Knoll, W.: Time-of-flight secondary ion mass spectrometry investigations of self-assembled monolayers of organic thiols, sulfides, and disulfides on gold surfaces. Langmuir 9(7), 1622–1624 (1993). American Chemical Society Hagenhoff, B., Benninghoven, A., Spinke, J., Liley, M., Knoll, W.: Time-of-flight secondary ion mass spectrometry investigations of self-assembled monolayers of organic thiols, sulfides, and disulfides on gold surfaces. Langmuir 9(7), 1622–1624 (1993). American Chemical Society
41.
Zurück zum Zitat Häkkinen, H.: The gold-sulfur interface at the nanoscale. Nat. Chem. 4(6), 443–455 (2012). Nature Publishing Group Häkkinen, H.: The gold-sulfur interface at the nanoscale. Nat. Chem. 4(6), 443–455 (2012). Nature Publishing Group
42.
Zurück zum Zitat Park, Y.S., et al.: Contact chemistry and single-molecule conductance: A comparison of phosphines, methyl sulfides, and amines. J. Am. Chem. Soc. 129(51), 15768–15769 (2007)PubMed Park, Y.S., et al.: Contact chemistry and single-molecule conductance: A comparison of phosphines, methyl sulfides, and amines. J. Am. Chem. Soc. 129(51), 15768–15769 (2007)PubMed
43.
Zurück zum Zitat Morf, P., et al.: Dithiocarbamates: functional and versatile linkers for the formation of self-assembled monolayers. Langmuir 22(2), 658–663 (2006)PubMed Morf, P., et al.: Dithiocarbamates: functional and versatile linkers for the formation of self-assembled monolayers. Langmuir 22(2), 658–663 (2006)PubMed
44.
Zurück zum Zitat Colorado, R., Villazana, R.J., Lee, T.R.: Self-assembled monolayers on gold generated from aliphatic dithiocarboxylic acids. Langmuir 14(22), 6337–6340 (1998) Colorado, R., Villazana, R.J., Lee, T.R.: Self-assembled monolayers on gold generated from aliphatic dithiocarboxylic acids. Langmuir 14(22), 6337–6340 (1998)
45.
Zurück zum Zitat Tierney, H.L., et al.: Experimental demonstration of a single-molecule electric motor. Nat. Nanotechnol. 6(10), 625–629 (2011)PubMed Tierney, H.L., et al.: Experimental demonstration of a single-molecule electric motor. Nat. Nanotechnol. 6(10), 625–629 (2011)PubMed
46.
Zurück zum Zitat Baber, A.E., Tierney, H.L., Sykes, E.C.H.: A quantitative single-molecule study of thioether molecular rotors. ACS Nano 2(11), 2385–2391 (2008)PubMed Baber, A.E., Tierney, H.L., Sykes, E.C.H.: A quantitative single-molecule study of thioether molecular rotors. ACS Nano 2(11), 2385–2391 (2008)PubMed
47.
Zurück zum Zitat Koumura, N., Geertsema, E.M., Meetsma, A., Feringa, B.L.: Light-driven molecular rotor: unidirectional rotation controlled by a single stereogenic center [6]. J. Am. Chem. Soc. 122(48), 12005–12006 (2000). American Chemical Society Koumura, N., Geertsema, E.M., Meetsma, A., Feringa, B.L.: Light-driven molecular rotor: unidirectional rotation controlled by a single stereogenic center [6]. J. Am. Chem. Soc. 122(48), 12005–12006 (2000). American Chemical Society
48.
Zurück zum Zitat Van Delden, R.A., Ter Wiel, M.K.J., Pollard, M.M., Vicario, J., Koumura, N., Feringa, B.L.: Unidirectional molecular motor on a gold surface. Nature 437(7063), 1337–1340 (2005)PubMed Van Delden, R.A., Ter Wiel, M.K.J., Pollard, M.M., Vicario, J., Koumura, N., Feringa, B.L.: Unidirectional molecular motor on a gold surface. Nature 437(7063), 1337–1340 (2005)PubMed
49.
Zurück zum Zitat Benneckendorf, F.S., et al.: Tetrapodal diazatriptycene enforces orthogonal orientation in self-assembled monolayers. ACS Appl. Mater. Interfaces. 12(5), 6565–6572 (2020)PubMed Benneckendorf, F.S., et al.: Tetrapodal diazatriptycene enforces orthogonal orientation in self-assembled monolayers. ACS Appl. Mater. Interfaces. 12(5), 6565–6572 (2020)PubMed
50.
Zurück zum Zitat Arroyo, C.R., Leary, E., Castellanos-Gómez, A., Rubio-Bollinger, G., González, M.T., Agraït, N.: Influence of binding groups on molecular junction formation. J. Am. Chem. Soc. 133(36), 14313–14319 (2011)PubMed Arroyo, C.R., Leary, E., Castellanos-Gómez, A., Rubio-Bollinger, G., González, M.T., Agraït, N.: Influence of binding groups on molecular junction formation. J. Am. Chem. Soc. 133(36), 14313–14319 (2011)PubMed
51.
Zurück zum Zitat Venkataraman, L., Klare, J.E., Tam, I.W., Nuckolls, C., Hybertsen, M.S., Steigerwald, M.L.: Single-molecule circuits with well-defined molecular conductance (2006) Venkataraman, L., Klare, J.E., Tam, I.W., Nuckolls, C., Hybertsen, M.S., Steigerwald, M.L.: Single-molecule circuits with well-defined molecular conductance (2006)
52.
Zurück zum Zitat Zhang, L., Cole, J.M.: Anchoring groups for dye-sensitized solar cells. ACS Appl. Mater. Interfaces 7(6), 3427–3455 (2015). American Chemical Society Zhang, L., Cole, J.M.: Anchoring groups for dye-sensitized solar cells. ACS Appl. Mater. Interfaces 7(6), 3427–3455 (2015). American Chemical Society
53.
Zurück zum Zitat Mishchenko, A., et al.: Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group. J. Am. Chem. Soc. 133(2), 184–187 (2010)PubMed Mishchenko, A., et al.: Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group. J. Am. Chem. Soc. 133(2), 184–187 (2010)PubMed
54.
Zurück zum Zitat Venkataraman, L., Klare, J.E., Tam, I.W., Nuckolls, C., Hybertsen, M.S., Steigerwald, M.L.: Single-molecule circuits with well-defined molecular conductance. Nano Lett. 6(3), 458–462 (2006)PubMed Venkataraman, L., Klare, J.E., Tam, I.W., Nuckolls, C., Hybertsen, M.S., Steigerwald, M.L.: Single-molecule circuits with well-defined molecular conductance. Nano Lett. 6(3), 458–462 (2006)PubMed
55.
Zurück zum Zitat Ie, Y., et al.: Nature of electron transport by pyridine-based tripodal anchors: Potential for robust and conductive single-molecule junctions with gold electrodes. J. Am. Chem. Soc. 133(9), 3014–3022 (2011)PubMed Ie, Y., et al.: Nature of electron transport by pyridine-based tripodal anchors: Potential for robust and conductive single-molecule junctions with gold electrodes. J. Am. Chem. Soc. 133(9), 3014–3022 (2011)PubMed
56.
Zurück zum Zitat Gao, L., et al.: Constructing an array of anchored single-molecule rotors on gold surfaces. Phys. Rev. Lett. 101(19), 197209 (2008)PubMed Gao, L., et al.: Constructing an array of anchored single-molecule rotors on gold surfaces. Phys. Rev. Lett. 101(19), 197209 (2008)PubMed
57.
Zurück zum Zitat Kirmse, W.: The beginnings of N-Heterocyclic carbenes. Angew. Chemie Int. Ed. 49(47), 8798–8801 (2010) Kirmse, W.: The beginnings of N-Heterocyclic carbenes. Angew. Chemie Int. Ed. 49(47), 8798–8801 (2010)
58.
Zurück zum Zitat Zhukhovitskiy, A.V., MacLeod, M.J., Johnson, J.A.: Carbene ligands in surface chemistry: from stabilization of discrete elemental allotropes to modification of nanoscale and bulk substrates. Chem. Rev. 115(20), 11503–11532 (2015)PubMed Zhukhovitskiy, A.V., MacLeod, M.J., Johnson, J.A.: Carbene ligands in surface chemistry: from stabilization of discrete elemental allotropes to modification of nanoscale and bulk substrates. Chem. Rev. 115(20), 11503–11532 (2015)PubMed
59.
Zurück zum Zitat Nguyen, D.T., et al.: Versatile micropatterns of N-Heterocyclic carbenes on gold surfaces: increased thermal and pattern stability with enhanced conductivity. Angew. Chemie Int. Ed. 57(35), 11465–11469 (2018) Nguyen, D.T., et al.: Versatile micropatterns of N-Heterocyclic carbenes on gold surfaces: increased thermal and pattern stability with enhanced conductivity. Angew. Chemie Int. Ed. 57(35), 11465–11469 (2018)
60.
Zurück zum Zitat H. Jacobsen, A. Correa, A. Poater, C. Costabile, and L. Cavallo, “Understanding the M–(NHC) (NHC = N-heterocyclic carbene) bond. Coord. Chem. Rev. 253(5–6), 687–703. Elsevier (2009) H. Jacobsen, A. Correa, A. Poater, C. Costabile, and L. Cavallo, “Understanding the M–(NHC) (NHC = N-heterocyclic carbene) bond. Coord. Chem. Rev. 253(5–6), 687–703. Elsevier (2009)
61.
Zurück zum Zitat Crudden, C.M., et al.: Simple direct formation of self-assembled N-heterocyclic carbene monolayers on gold and their application in biosensing. Nat. Commun. 7(1), 1–7 (2016) Crudden, C.M., et al.: Simple direct formation of self-assembled N-heterocyclic carbene monolayers on gold and their application in biosensing. Nat. Commun. 7(1), 1–7 (2016)
62.
Zurück zum Zitat Zhukhovitskiy, A.V., Mavros, M.G., Van Voorhis, T., Johnson, J.A.: Addressable Carbene Anchors for Gold Surfaces. J. Am. Chem. Soc. 135(20), 7418–7421 (2013)PubMed Zhukhovitskiy, A.V., Mavros, M.G., Van Voorhis, T., Johnson, J.A.: Addressable Carbene Anchors for Gold Surfaces. J. Am. Chem. Soc. 135(20), 7418–7421 (2013)PubMed
63.
Zurück zum Zitat Crudden, C.M., et al.: Ultra stable self-assembled monolayers of N-heterocyclic carbenes on gold. Nat. Chem. 6(5), 409–414 (2014)PubMed Crudden, C.M., et al.: Ultra stable self-assembled monolayers of N-heterocyclic carbenes on gold. Nat. Chem. 6(5), 409–414 (2014)PubMed
64.
Zurück zum Zitat Dery, S. et al.: Flexible NO2 ‐functionalized N‐Heterocyclic carbene monolayers on Au (111) surface. Chem.A Eur. J. 25(66), 15067–15072 (2019) Dery, S. et al.: Flexible NO2 ‐functionalized N‐Heterocyclic carbene monolayers on Au (111) surface. Chem.A Eur. J. 25(66), 15067–15072 (2019)
65.
Zurück zum Zitat Bakker, A., et al.: Elucidating the binding modes of N-Heterocyclic carbenes on a gold surface. J. Am. Chem. Soc. 140(38), 11889–11892 (2018)PubMed Bakker, A., et al.: Elucidating the binding modes of N-Heterocyclic carbenes on a gold surface. J. Am. Chem. Soc. 140(38), 11889–11892 (2018)PubMed
66.
Zurück zum Zitat Larrea, C.R., Baddeley, C.J., Narouz, M.R., Mosey, N.J., Horton, J.H., Crudden, C.M.: N -Heterocyclic carbene self-assembled monolayers on copper and gold: dramatic effect of wingtip groups on binding, orientation and assembly. ChemPhysChem 18(24), 3536–3539 (2017)PubMedPubMedCentral Larrea, C.R., Baddeley, C.J., Narouz, M.R., Mosey, N.J., Horton, J.H., Crudden, C.M.: N -Heterocyclic carbene self-assembled monolayers on copper and gold: dramatic effect of wingtip groups on binding, orientation and assembly. ChemPhysChem 18(24), 3536–3539 (2017)PubMedPubMedCentral
67.
Zurück zum Zitat Wang, G., et al.: Ballbot-type motion of N-heterocyclic carbenes on gold surfaces. Nat. Chem. 9(2), 152–156 (2017)PubMed Wang, G., et al.: Ballbot-type motion of N-heterocyclic carbenes on gold surfaces. Nat. Chem. 9(2), 152–156 (2017)PubMed
68.
Zurück zum Zitat Zhang, Z., Imae, T.: Hydrogen-bonding stabilized self-assembled monolayer film of a functionalized diacid, protoporphyrin IX Zinc(II), onto a gold surface. Nano Lett. 1(5), 241–243 (2001) Zhang, Z., Imae, T.: Hydrogen-bonding stabilized self-assembled monolayer film of a functionalized diacid, protoporphyrin IX Zinc(II), onto a gold surface. Nano Lett. 1(5), 241–243 (2001)
69.
Zurück zum Zitat Rochford, J., Chu, D., Hagfeldt, A., Galoppini, E.: Tetrachelate porphyrin chromophores for metal oxide semiconductor sensitization: Effect of the spacer length and anchoring group position. J. Am. Chem. Soc. 129(15), 4655–4665 (2007)PubMed Rochford, J., Chu, D., Hagfeldt, A., Galoppini, E.: Tetrachelate porphyrin chromophores for metal oxide semiconductor sensitization: Effect of the spacer length and anchoring group position. J. Am. Chem. Soc. 129(15), 4655–4665 (2007)PubMed
70.
Zurück zum Zitat Zotti, L.A., et al.: Revealing the role of anchoring groups in the electrical conduction through single-molecule junctions. Small 6(14), 1529–1535 (2010)PubMed Zotti, L.A., et al.: Revealing the role of anchoring groups in the electrical conduction through single-molecule junctions. Small 6(14), 1529–1535 (2010)PubMed
71.
Zurück zum Zitat Eisenhut, F., Meyer, J., Krüger, J., Ohmann, R., Cuniberti, G., Moresco, F.: Inducing the controlled rotation of single o-MeO-DMBI molecules anchored on Au(111). Surf. Sci. 678, 177–182 (2018) Eisenhut, F., Meyer, J., Krüger, J., Ohmann, R., Cuniberti, G., Moresco, F.: Inducing the controlled rotation of single o-MeO-DMBI molecules anchored on Au(111). Surf. Sci. 678, 177–182 (2018)
72.
Zurück zum Zitat Tao, Y.T.: Structural comparison of self-assembled monolayers of n-Alkanoic acids on the surfaces of silver, copper, and aluminum. J. Am. Chem. Soc. 115(10), 4350–4358 (1993) Tao, Y.T.: Structural comparison of self-assembled monolayers of n-Alkanoic acids on the surfaces of silver, copper, and aluminum. J. Am. Chem. Soc. 115(10), 4350–4358 (1993)
73.
Zurück zum Zitat Krzykawska, A., Ossowski, J., Zaba, T., Cyganik, P.: Binding groups for highly ordered SAM formation: carboxylic: versus thiol. Chem. Commun. 53(42), 5748–5751 (2017) Krzykawska, A., Ossowski, J., Zaba, T., Cyganik, P.: Binding groups for highly ordered SAM formation: carboxylic: versus thiol. Chem. Commun. 53(42), 5748–5751 (2017)
74.
Zurück zum Zitat Han, S.W., Ha, T.H., Kim, C.H., Kim, K.: Self-assembly of anthraquinone-2-carboxylic acid on silver: fourier transform infrared spectroscopy, ellipsometry, quartz crystal microbalance, and atomic force microscopy study. Langmuir 14(21), 6113–6120 (1998) Han, S.W., Ha, T.H., Kim, C.H., Kim, K.: Self-assembly of anthraquinone-2-carboxylic acid on silver: fourier transform infrared spectroscopy, ellipsometry, quartz crystal microbalance, and atomic force microscopy study. Langmuir 14(21), 6113–6120 (1998)
75.
Zurück zum Zitat Ahn, S., et al.: Electronic transport and mechanical stability of carboxyl linked single-molecule junctions. Phys. Chem. Chem. Phys. 14(40), 13841–13845 (2012)PubMed Ahn, S., et al.: Electronic transport and mechanical stability of carboxyl linked single-molecule junctions. Phys. Chem. Chem. Phys. 14(40), 13841–13845 (2012)PubMed
76.
Zurück zum Zitat Matsuo, Y., Kanaizuka, K., Matsuo, K., Zhong, Y.W., Nakae, T., Nakamura, E.: Photocurrent-generating properties of organometallic fullerene molecules on an electrode. J. Am. Chem. Soc. 130(15), 5016–5017 (2008)PubMed Matsuo, Y., Kanaizuka, K., Matsuo, K., Zhong, Y.W., Nakae, T., Nakamura, E.: Photocurrent-generating properties of organometallic fullerene molecules on an electrode. J. Am. Chem. Soc. 130(15), 5016–5017 (2008)PubMed
77.
Zurück zum Zitat Olavarria-Contreras, I.J., Perrin, M.L., Chen, Z., Klyatskaya, S., Ruben, M., Van Der Zant, H.S.J.: C-Au covalently bonded molecular junctions using nonprotected Alkynyl anchoring groups. J. Am. Chem. Soc. 138(27), 8465–8469 (2016)PubMed Olavarria-Contreras, I.J., Perrin, M.L., Chen, Z., Klyatskaya, S., Ruben, M., Van Der Zant, H.S.J.: C-Au covalently bonded molecular junctions using nonprotected Alkynyl anchoring groups. J. Am. Chem. Soc. 138(27), 8465–8469 (2016)PubMed
78.
Zurück zum Zitat Liu, J., et al.: Triptycene-terminated thiolate and selenolate monolayers on Au(111). Beilstein J. Nanotechnol. 8(1), 892–905 (2017)PubMedPubMedCentral Liu, J., et al.: Triptycene-terminated thiolate and selenolate monolayers on Au(111). Beilstein J. Nanotechnol. 8(1), 892–905 (2017)PubMedPubMedCentral
79.
Zurück zum Zitat Schull, G., Néel, N., Becker, M., Kröger, J., Berndt, R.: Spatially resolved conductance of oriented C 60. New J. Phys. 10(6), 065012 (2008) Schull, G., Néel, N., Becker, M., Kröger, J., Berndt, R.: Spatially resolved conductance of oriented C 60. New J. Phys. 10(6), 065012 (2008)
80.
Zurück zum Zitat Valášek, M., Edelmann, K., Gerhard, L., Fuhr, O., Lukas, M., Mayor, M.: Synthesis of molecular tripods based on a rigid 9, 9’-spirobifluorene scaffold. J. Org. Chem. 79(16), 7342–7357 (2014)PubMed Valášek, M., Edelmann, K., Gerhard, L., Fuhr, O., Lukas, M., Mayor, M.: Synthesis of molecular tripods based on a rigid 9, 9’-spirobifluorene scaffold. J. Org. Chem. 79(16), 7342–7357 (2014)PubMed
81.
Zurück zum Zitat Shirai, Y., Cheng, L., Chen, B., Tour, J.M.: Characterization of self-assembled monolayers of fullerene derivatives on gold surfaces: Implications for device evaluations. J. Am. Chem. Soc. 128(41), 13479–13489 (2006)PubMed Shirai, Y., Cheng, L., Chen, B., Tour, J.M.: Characterization of self-assembled monolayers of fullerene derivatives on gold surfaces: Implications for device evaluations. J. Am. Chem. Soc. 128(41), 13479–13489 (2006)PubMed
82.
Zurück zum Zitat O’Driscoll, L.J., et al.: Carbazole-based tetrapodal anchor groups for gold surfaces: synthesis and conductance properties. Angew. Chemie 132(2), 892–899 (2020) O’Driscoll, L.J., et al.: Carbazole-based tetrapodal anchor groups for gold surfaces: synthesis and conductance properties. Angew. Chemie 132(2), 892–899 (2020)
83.
Zurück zum Zitat Hirose, T., Ie, Y., Aso, Y.: Synthesis of tripodal-anchor units having pyridine or amine functional groups and their adsorption behavior on metal electrodes. Chem. Lett. 40(2), 204–205 (2011) Hirose, T., Ie, Y., Aso, Y.: Synthesis of tripodal-anchor units having pyridine or amine functional groups and their adsorption behavior on metal electrodes. Chem. Lett. 40(2), 204–205 (2011)
84.
Zurück zum Zitat Zarwell, S., Dietrich, S., Schulz, C., Dietrich, P., Michalik, F., Rück-Braun, K.: Preparation of an Indolylfulgimide-Adamantane Linker Conjugate with Nitrile Anchoring Groups through Palladium-Catalyzed transformations. European J. Org. Chem. 2009(13), 2088–2095 (2009) Zarwell, S., Dietrich, S., Schulz, C., Dietrich, P., Michalik, F., Rück-Braun, K.: Preparation of an Indolylfulgimide-Adamantane Linker Conjugate with Nitrile Anchoring Groups through Palladium-Catalyzed transformations. European J. Org. Chem. 2009(13), 2088–2095 (2009)
Metadaten
Titel
Chemical Anchoring of Molecular Rotors
verfasst von
Oumaima Aiboudi
Franziska Lissel
Copyright-Jahr
2020
DOI
https://doi.org/10.1007/978-3-030-56777-4_7

    Marktübersichten

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