Abstract
The synthesis of a molecular wire assembly is a key technology to construct molecular architectures toward single-molecular organic electronic devices. Two new methods to fabricate highly organized and assembled molecular wires are described: 1. one-dimensionally assembled polythiophene molecular wires by electrochemical epitaxial polymerization; 2. multilayered graphene nanoribbon assemblies by two-zone chemical vapor deposition.
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Parodi, M., Bianco, B., Chiabrera, A.: Toward molecular electronics. Self-screening of molecular wires. Cell Biophys. 7(3), 215–235 (1985). doi:10.1007/BF02790467
Barth, J.V.: Molecular architectonic on metal surfaces. Annu. Rev. Phys. Chem. 58(1), 375–407 (2007). doi:10.1146/annurev.physchem.56.092503.141259
El Garah, M., MacLeod, J.M., Rosei, F.: Covalently bonded networks through surface-confined polymerization. Surf. Sci. 613, 6–14 (2013). doi:10.1016/j.susc.2013.03.015
Sirringhaus, H., Brown, P.J., Friend, R.H., Nielsen, M.M., Bechgaard, K., Langeveld-Voss, B.M.W., Spiering, A.J.H., Janssen, R.A.J., Meijer, E.W., Herwig, P., de Leeuw, D.M.: Two-dimensional charge transport in self-organized, high-mobility conjugated polymers. Nature 401(6754), 685–688 (1999). doi:10.1038/44359
Dimitrakopoulos, C.D., Mascaro, D.J.: Organic thin-film transistors: a review of recent advances. IBM J. Res. Dev. 45(1), 11–27 (2001).
Friend, R.H., Gymer, R.W., Holmes, A.B., Burroughes, J.H., Marks, R.N., Taliani, C., Bradley, D.D.C., Dos Santos, D.A., Brédas, J.L., Lögdlund, M., Salaneck, R.: Conjugated polymer electroluminescence. Nature 397(6715), 121–128 (1999). doi:10.1038/16393
Gross, M., Müller, D.C., Nothofer, H.-G., Scherf, U., Neher, D., Bräuchle, C., Meerholz, K.: Improving the performance of doped π-conjugated polymers for use in organic light-emitting diodes. Nature 405(6787), 661–665 (2000). doi:10.1038/35015037
Yu, G., Gao, J., Hummelen, J.C., Wudl, F., Heeger, A.J.: Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270(5243), 1789–1791 (1995). doi:10.1126/science.270.5243-1789
Granström, M., Petritsch, K., Arias, A.C., Lux, A., Andersson, M.R., Friend, R.H.: Laminated fabrication of polymeric photovoltaic diodes. Nature 395(6699), 257–260 (1998). doi:10.1038/26183
Sakaguchi, H., Matsumura, H., Gong, H.: Electrochemical epitaxial polymerization of single-molecular wires. Nat. Mater. 3(8), 551–557 (2004). doi:10.1038/nmat1176
Okawa, Y., Aono, M.: Nanoscale control of chain polymerization. Nature 409(6821), 683–684 (2001). doi:10.1038/35055625
Okawa, Y., Aono, M.: Linear chain polymerization initiated by a scanning tunneling microscope tip at designated positions. J. Chem. Phys. 115(5), 2317–2322 (2001). doi:10.1063/1.1384554
Sakaguchi, H., Matsumura, H., Gong, H., Abouelwafa, A.M.: Direct visualization of the formation of single-molecule conjugated copolymers. Science 310(5750), 1002–1006 (2005). doi:10.1126/science.1117990
Chen, L., Hernandez, Y., Feng, X., Müllen, K.: From nanographene and graphene nanoribbons to graphene sheets: chemical synthesis. Angew. Chem. Int. Ed. 51(31), 7640–7654 (2012). doi:10.1002/anie.201201084
Geim, A.K.: Nobel lecture: random walk to graphene. Rev. Mod. Phys. 83(3), 851–862 (2011). doi:10.1103/RevModPhys.83.851
Jiao, L., Zhang, L., Wang, X., Diankov, G., Dai, H.: Narrow graphene nanoribbons from carbon nanotubes. Nature 458(7240), 877–880 (2009). doi:10.1038/nature07919
Kosynkin, D.V., Higginbotham, A.L., Sinitskii, A., Lomeda, J.R., Dimiev, A., Price, B.K., Tour, J.M.: Longitudinal unzipping of carbon nanotubes to form graphene nanoribbons. Nature 458(7240), 872–876 (2009). doi:10.1038/nature07872
Wang, X., Dai, H.: Etching and narrowing of graphene from the edges. Nat. Chem. 2(8), 661–665 (2010). doi:10.1038/nchem.719
Kato, T., Hatakeyama, R.: Site-and alignment-controlled growth of graphene nanoribbons from nickel nanobars. Nat. Nanotech. 7(10), 651–656 (2012). doi:10.1038/nnano.2012.145
Sakaguchi, H., Kawagoe, Y., Hirano, Y., Iruka, T., Yano, M., Nakae, T.: Width-controlled sub-nanometer graphene nanoribbon films synthesized by radical-polymerized chemical vapor deposition. Adv. Mater. 26(24), 4134–4138 (2014). doi:10.1002/adma.201305034
Tao, N.J., Lindsay, S.M.: In situ scanning tunneling microscopy study of iodine and bromine adsorption on gold (111) under potential control. J. Phys. Chem. 96(13), 5213–5217 (1992). doi:10.1021/j100192a006
Yamada, T., Batina, N., Itaya, K.: Structure of electrochemically deposited iodine adlayer on Au (111) studied by ultrahigh-vacuum instrumentation and in situ STM. J. Phys. Chem. 99(21), 8817–8823 (1995). doi:10.1021/j100021a057
Furukawa, Y.: Electronic absorption and vibrational spectroscopies of conjugated conducting polymers. J. Phys. Chem. 100(39), 15644–15653 (1996). doi:10.1021/jp960608n
Bakhshi, A., Deepika: Molecular designing of copolymers of donor–acceptor polymers based on polythiophene. J. Mol. Struct. THEOCHEM 499(1), 105–110 (2000). doi:10.1016/S0166-1280(99)00275-4
Iyoda, T., Toyoda, H., Fujitsuka, M., Nakahara, R., Tsuchiya, H., Honda, K., Shimidzu, T.: The 100-Å-order depth profile control of polypyrrole-poly (3-methylthiophene) composite thin film by potential-programmed electropolymerization. J. Phys. Chem. 95(13), 5215–5220 (1991). doi:10.1021/j100166a055
Sirringhaus, H., Wilson, R.J., Friend, R.H., Inbasekaran, M., Wu, W., Woo, E.P., Grell, M., Bradley, D.D.C.: Mobility enhancement in conjugated polymer field-effect transistors through chain alignment in a liquid-crystalline phase. Appl. Phys. Lett. 77(3), 406–408 (2000). doi:10.1063/1.126991
Brun, M., Demadrille, R., Rannou, P., Pron, A., Travers, J.-P., Grévin, B.: Multiscale scanning tunneling microscopy study of self-assembly phenomena in two-dimensional polycrystals of π-conjugated polymers: the case of regioregular poly (dioctylbithiophene-alt-fluorenone). Adv. Mater. 16(23–24), 2087–2092 (2004). doi:10.1002/adma.200400088
Ng, M.-K., Yu, L.: Synthesis of amphiphilic conjugated diblock oligomers as molecular diodes. Angew. Chem. Int. Ed. 41(19), 3598–3601 (2002). doi:10.1002/1521-3773(20021004)41:19<3598:AID-ANIE3598>3.0.CO;2-U
Ng, M.-K., Lee, D.-C., Yu, L.: Molecular diodes based on conjugated diblock co-oligomers. J. Am. Chem. Soc. 124(40), 11862–11863 (2002). doi:10.1021/ja026808w
Leclerc, M., Daoust, G.: Design of new conducting 3,4-disubstituted polythiophenes. J. Chem. Soc., Chem. Commun. (3), 273–274 (1990). doi:10.1039/c39900000273
Daoust, G., Leclerc, M.: Structure-property relationships in alkoxy-substituted polythiophenes. Macromolecules 24(2), 455–459 (1991). doi:10.1021/ma00002a018
Johansson, T., Mammo, W., Svensson, M., Andersson, M.R., Inganäs, O.: Electrochemical bandgaps of substituted polythiophenes. J. Mater. Chem. 13(6), 1316–1323 (2003). doi:10.1039/b301403g
Leclerc, M.: Optical and electrochemical transducers based on functionalized conjugated polymers. Adv. Mater. 11(18), 1491–1498 (1999). doi:10.1002/(Sici)1521-4095(199912)11:18<1491:Aid-Adma1491>3.0.Co;2-O
Roux, C., Leclerc, M.: Rod-to-coil transition in alkoxy-substituted polythiophenes. Macromolecules 25(8), 2141–2144 (1992). doi:10.1021/ma00034a012
Gigli, G., Lomascolo, M., Cingolani, R., Barbarella, G., Zambianchi, M., Antolini, L., Della Sala, F., Di Carlo, A., Lugli, P.: Relationship between optical and structural properties in substituted quaterthiophene crystals. Appl. Phys. Lett. 73(17), 2414–2416 (1998). doi:10.1063/1.122451
Mena-Osteritz, E., Meyer, A., Langeveld-Voss, B.M.W., Janssen, R.A.J., Meijer, E.W., Bäuerle, P.: Two-dimensional crystals of poly (3-alkylthiophene)s: direct visualization of chain conformations of polymer folds in highly ordered 2D-latices of poly (3-alkylthiophenes). Angew. Chem. Int. Ed. 39(15), 2679–2684 (2000). doi:10.1002/1521-3773(20000804)39:15<2679::AID-ANIE2679>3.0.CO;2-2
Grévin, B., Rannou, P., Payerne, R., Pron, A., Travers, J.-P.: Scanning tunneling microscopy investigations of self-organized poly (3-hexylthiophene) two-dimensional polycrystals. Adv. Mater. 15(11), 881–884 (2003). doi:10.1002/adma.200304580
Grévin, B., Rannou, P., Payerne, R., Pron, A., Travers, J.-P.: Multi-scale scanning tunneling microscopy imaging of self-organized regioregular poly (3-hexylthiophene) films. J. Chem. Phys. 118(15), 7097–7102 (2003). doi:10.1063/1.1561435
Barbarella, G., Zambianchi, M., Bongini, A., Antolini, L.: Crystal structure of 4,4′,3″,4″′-tetramethyl2,2′:5′,2″:5″,2″′-tetrathiophene: a comparison with the conformation in solution. Adv. Mater. 4(4), 282–285 (1992). doi:10.1002/adma.19920040408
Grobis, M., Wachowiak, A., Yamachika, R., Crommie, M.F.: Tuning negative differential resistance in a molecular film. Appl. Phys. Lett. 86(20), 204102 (2005). doi:10.1063/1.1931822
Akai-Kasaya, M., Shimizu, K., Watanabe, Y., Saito, A., Aono, M., Kuwahara, Y.: Electronic structure of a polydiacetylene nanowire fabricated on highly ordered pyrolytic graphite. Phys. Rev. Lett. 91(25), 255501 (2003). doi:10.1103/PhysRevLett.91.255501
Schwierz, F.: Graphene transistors. Nat. Nanotech. 5(7), 487–496 (2010). doi:10.1038/nnano.2010.89
Schwab, M.G., Narita, A., Hernandez, Y., Balandina, T., Mali, K.S., De Feyter, S., Feng, X., Müllen, K.: Structurally defined graphene nanoribbons with high lateral extension. J. Am. Chem. Soc. 134(44), 18169–18172 (2012). doi:10.1021/ja307697j
Chuvilin, A., Bichoutskaia, E., Gimenez-Lopez, M.C., Chamberlain, T.W., Rance, G.A., Kuganathan, N., Biskupek, J., Kaiser, U., Khlobystov, A.N.: Self-assembly of a sulphur-terminated graphene nanoribbon within a single-walled carbon nanotube. Nat. Mater. 10(9), 687–692 (2011). doi:10.1038/nmat3082
Talyzin, A.V., Anoshkin, I.V., Krasheninnikov, A.V., Nieminen, R.M., Nasibulin, A.G., Jiang, H., Kauppinen, E.I.: Synthesis of graphene nanoribbons encapsulated in single-walled carbon nanotubes. Nano Lett. 11(10), 4352–4356 (2011). doi:10.1021/nl2024678
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(7305), 470–473 (2010). doi:10.1038/nature09211
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(3), 215–220 (2012). doi:10.1038/nchem.1242
Bronner, C., Stremlau, S., Gille, M., Brauße, F., Haase, A., Hecht, S., Tegeder, P.: Aligning the band gap of graphene nanoribbons by monomer doping. Angew. Chem. Int. Ed. 52(16), 4422–4425 (2013). doi:10.1002/anie.201209735
Zhu, X., Su, H.: Scaling of excitons in graphene nanoribbons with armchair shaped edges. J. Phys. Chem. A 115(43), 11998–12003 (2011). doi:10.1021/jp202787h
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). doi:10.1021/ja400304b
Simonov, K.A., Vinogradov, N.A., Vinogradov, A.S., Generalov, A.V., Zagrebina, E.M., Mårtensson, N., Cafolla, A.A., Carpy, T., Cunniffe, J.P., Preobrajenski, A.B.: Effect of substrate chemistry on the bottom-up fabrication of graphene nanoribbons: combined core-level spectroscopy and STM study. J. Phys. Chem. C 118(23), 12532–12540 (2014). doi:10.1021/jp502215m
Batra, A., Cvetko, D., Kladnik, G., Adak, O., Cardoso, C., Ferretti, A., Prezzi, D., Molinari, E., Morgante, A., Venkataraman, L.: Probing the mechanism for graphene nanoribbon formation on gold surfaces through X-ray spectroscopy. Chem. Sci. 5(11), 4419–4423 (2014). doi:10.1039/c4sc01584c
Gille, M., Viertel, A., Weidner, S., Hecht, S.: Modular synthesis of monomers for on-surface polymerization to graphene architectures. Synlett 24(2), 259–263 (2013). doi:10.1055/s-0032-1317959
Bennett, P.B., Pedramrazi, Z., Madani, A., Chen, Y.-C., de Oteyza, D.G., Chen, C., Fischer, F.R., Crommie, M.F., Bokor, J.: Bottom-up graphene nanoribbon field-effect transistors. Appl. Phys. Lett. 103(25), 253114 (2013). doi:10.1063/1.4855116
Tanaka, K., Yamashita, S., Yamabe, H., Yamabe, T.: Electronic properties of one-dimensional graphite family. Synth. Met. 17(1–3), 143–148 (1987). doi:10.1016/0379-6779(87)90729-6
Son, Y.-W., Cohen, M.L., Louie, S.G.: Energy gaps in graphene nanoribbons. Phys. Rev. Lett. 97(21), 216803 (2006). doi:10.1103/PhysRevLett.97.216803
Barone, V., Hod, O., Scuseria, G.E.: Electronic structure and stability of semiconducting graphene nanoribbons. Nano Lett. 6(12), 2748–2754 (2006). doi:10.1021/nl0617033
Huang, H., Wei, D., Sun, J., Wong, S.L., Feng, Y.P., Castro Neto, A.H., Wee, A.T.S.: Spatially resolved electronic structures of atomically precise armchair graphene nanoribbons. Sci. Rep. 2, 983 (2012). doi:10.1038/srep00983
Dienel, T., Kawai, S., Söde, H., Feng, X., Müllen, K., Ruffieux, P., Fasel, R., Gröning, O.: Resolving atomic connectivity in graphene nanostructure junctions. Nano Lett. 15(8), 5185–5190 (2015). doi:10.1021/acs.nanolett.5b01403
Sakaguchi, H., Song, S., Kojima, T., Nakae, T.: Homochiral polymerization-driven selective growth of graphene nanoribbons. Nat. Chem. 9(1), 57–63 (2017). doi:10.1038/nchem.2614
Sakamoto, J., van Heijst, J., Lukin, O., Schlüter, A.D.: Two-dimensional polymers: just a dream of synthetic chemists? Angew. Chem. Int. Ed. 48(6), 1030–1069 (2009). doi:10.1002/anie.200801863
Acknowledgements
This work is supported by Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Architectonics: Orchestration of Single Molecules for Novel Functions” (16H00967, 26110513) from the Japanese Ministry of Education, Culture, Sports, Sciences and Technology.
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Nakae, T., Sakaguchi, H. (2017). Surface Synthesis of Molecular Wire Architectures. In: Ogawa, T. (eds) Molecular Architectonics. Advances in Atom and Single Molecule Machines. Springer, Cham. https://doi.org/10.1007/978-3-319-57096-9_19
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