Abstract
We apply the NEGF + DFT technique to study the effect of anchoring groups on the electronic transport properties of a single pyrene molecule attached to two Au electrodes via three different anchoring groups (namely NO2, NH2 and CN). More specifically, we investigate the effect of asymmetric electrode coupling together with B and N doping on rectification ratio of a pyrene-based molecular device. The results indicate that the rectification ratio can be tuned by selecting configurations of maximum difference in the coupling parameters in the two sides of the gold electrodes, and its magnitude depends on the strength of the electronic coupling of the pyrene molecule to the gold electrodes. In addition, we observe that doping the molecule with B and N atoms decreases the coupling parameters by creating a resonant peak close to the Fermi level.
Similar content being viewed by others
References
Aviram, A., Ratner, M.A.: Molecular rectifiers. Chem. Phys. Lett. 29(2), 277–283 (1974)
Tsutsui, M., Teramae, Y., Kurokawa, S., Sakai, A.: High-conductance states of single benzenedithiol molecules. Appl. Phys. Lett. 89(16), 163111 (2006)
Néel, N., Kröger, J., Limot, L., Berndt, R.: Conductance of oriented C60 molecules. Nano Lett. 8(5), 1291–1295 (2008)
Mishchenko, A., Zotti, L.A., Vonlanthen, D., Bürkle, M., Pauly, F., Cuevas, J.C., Wandlowski, T.: Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group. J. Am. Chem. Soc. 133(2), 184–187 (2010)
Chiechi, R.C., Weiss, E.A., Dickey, M.D., Whitesides, G.M.: Eutectic gallium–indium (EGaIn): a moldable liquid metal for electrical characterization of self-assembled monolayers. Angew. Chem. 120(1), 148–150 (2008)
Temirov, R., Lassise, A., Anders, F.B., Tautz, F.S.: Kondo effect by controlled cleavage of a single-molecule contact. Nanotechnology 19(6), 065401 (2008)
An, Y.P., Yang, Z., Ratner, M.A.: High-efficiency switching effect in porphyrin-ethyne-benzene conjugates. J. Chem. Phys. 135(4), 044706 (2011)
Fan, Z.Q., Zhang, Z.H., Qiu, M., Tang, G.P.: Rectifying performance and reversible conductance switching of single-polyaniline devices. Phys. Lett. A 375(37), 3314–3318 (2011)
Min, Y., Yao, K.L., Fu, H.H., Liu, Z.L., Li, Q.: First-principles study of strong rectification and negative differential resistance induced by charge distribution in single molecule. J. Chem. Phys. 132(21), 214703 (2010)
Fan, Z.Q., Chen, K.Q.: Negative differential resistance and rectifying behaviors in phenalenyl molecular device with different contact geometries. Appl. Phys. Lett. 96(5), 053509 (2010)
Saffarzadeh, A., Farghadan, R.: A spin-filter device based on armchair graphene nanoribbons. Appl. Phys. Lett. 98(2), 023106 (2011)
Zhu, L., Yao, K.L., Liu, Z.L.: Molecular spin valve and spin filter composed of single-molecule magnets. Appl. Phys. Lett. 96(8), 082115 (2010)
Ren, Y., Chen, K.Q., Wan, Q., Zou, B.S., Zhang, Y.: Transitions between semiconductor and metal induced by mixed deformation in carbon nanotube devices. Appl. Phys. Lett. 94(18), 183506 (2009)
An, Y., Yang, Z.: Abnormal electronic transport and negative differential resistance of graphene nanoribbons with defects. Appl. Phys. Lett. 99(19), 192102 (2011)
Long, M.Q., Chen, K.Q., Wang, L., Qing, W., Zou, B.S., Shuai, Z.: Negative differential resistance behaviors in porphyrin molecular junctions modulated with side groups. Appl. Phys. Lett. 92(24), 215 (2008)
Pan, H., Zhang, Y.W., Shenoy, V.B., Gao, H.: Effects of H-, N-, and (H, N)-doping on the photocatalytic activity of TiO2. J. Phys. Chem. C 115(24), 12224–12231 (2011)
Müller, K.H.: Effect of the atomic configuration of gold electrodes on the electrical conduction of alkanedithiol molecules. Phys. Rev. B 73(4), 045403 (2006)
Hu, Y., Zhu, Y., Gao, H., Guo, H.: Conductance of an ensemble of molecular wires: a statistical analysis. Phys. Rev. Lett. 95(15), 156803 (2005)
Basch, H., Cohen, R., Ratner, M.A.: Interface geometry and molecular junction conductance: geometric fluctuation and stochastic switching. Nano Lett. 5(9), 1668–1675 (2005)
Ke, S.H., Baranger, H.U., Yang, W.: Molecular conductance: chemical trends of anchoring groups. J. Am. Chem. Soc. 126(48), 15897–15904 (2004)
Dell’Angela, M., Kladnik, G., Cossaro, A., Verdini, A., Kamenetska, M., Tamblyn, I., Venkataraman, L.: Relating energy level alignment and amine-linked single molecule junction conductance. Nano Lett. 10(7), 2470–2474 (2010)
Darancet, P., Widawsky, J.R., Choi, H.J., Venkataraman, L., Neaton, J.B.: Quantitative current–voltage characteristics in molecular junctions from first principles. Nano Lett. 12(12), 6250–6254 (2012)
Wickenburg, S., Lu, J., Lischner, J., Tsai, H.Z., Omrani, A.A., Riss, A., Wong, D.: Tuning charge and correlation effects for a single molecule on a graphene device. Nat. Commun. 7, 13553 (2016)
Kamenetska, M., Koentopp, M., Whalley, A.C., Park, Y.S., Steigerwald, M.L., Nuckolls, C., Venkataraman, L.: Formation and evolution of single-molecule junctions. Phys. Rev. Lett. 102(12), 126803 (2009)
Lörtscher, E., Cho, C.J., Mayor, M., Tschudy, M., Rettner, C., Riel, H.: Influence of the anchor group on charge transport through single-molecule junctions. ChemPhysChem 12(9), 1677–1682 (2011)
Li, Z., Smeu, M., Ratner, M.A., Borguet, E.: Effect of anchoring groups on single molecule charge transport through porphyrins. J. Phys. Chem. C 117(29), 14890–14898 (2013)
Ulrich, J., Esrail, D., Pontius, W., Venkataraman, L., Millar, D., Doerrer, L.H.: Variability of conductance in molecular junctions. J. Phys. Chem. B 110(6), 2462–2466 (2006)
Li, C., Pobelov, I., Wandlowski, T., Bagrets, A., Arnold, A., Evers, F.: Charge transport in single Au| alkanedithiol| Au junctions: coordination geometries and conformational degrees of freedom. J. Am. Chem. Soc. 130(1), 318–326 (2008)
Yasuda, S., Yoshida, S., Sasaki, J., Okutsu, Y., Nakamura, T., Taninaka, A., Shigekawa, H.: Bond fluctuation of S/Se anchoring observed in single-molecule conductance measurements using the point contact method with scanning tunneling microscopy. J. Am. Chem. Soc. 128(24), 7746–7747 (2006)
Zhang, Z., Yoshida, N., Imae, T., Xue, Q., Bai, M., Jiang, J., Liu, Z.: A self-assembled monolayer of an alkanoic acid-derivatized porphyrin on gold surface: a structural investigation by surface plasmon resonance, ultraviolet–visible, and infrared spectroscopies. J. Colloid Interface Sci. 243(2), 382–387 (2001)
Heera, T.R., Cindrella, L.: Molecular orbital evaluation of charge flow dynamics in natural pigments based photosensitizers. J. Mol. Model. 16(3), 523–533 (2010)
Cheng, Z.L., Skouta, R., Vazquez, H., Widawsky, J.R., Schneebeli, S., Chen, W., Venkataraman, L.: In situ formation of highly conducting covalent Au–C contacts for single-molecule junctions. Nat. Nanotechnol. 6(6), 353–357 (2011)
Schull, G., Frederiksen, T., Arnau, A., Sánchez-Portal, D., Berndt, R.: Atomic-scale engineering of electrodes for single-molecule contacts. Nat. Nanotechnol. 6(1), 23–27 (2011)
Frei, M., Aradhya, S.V., Koentopp, M., Hybertsen, M.S., Venkataraman, L.: Mechanics and chemistry: single molecule bond rupture forces correlate with molecular backbone structure. Nano Lett. 11(4), 1518–1523 (2011)
Hong, W., Manrique, D.Z., Moreno-Garcia, P., Gulcur, M., Mishchenko, A., Lambert, C.J., Wandlowski, T.: Single molecular conductance of tolanes: experimental and theoretical study on the junction evolution dependent on the anchoring group. J. Am. Chem. Soc. 134(4), 2292–2304 (2012)
Lörtscher, E., Cho, C.J., Mayor, M., Tschudy, M., Rettner, C., Riel, H.: Influence of the anchor group on charge transport through single-molecule junctions. ChemPhysChem 12(9), 1677–1682 (2011)
Zotti, L.A., Kirchner, T., Cuevas, J.C., Pauly, F., Huhn, T., Scheer, E., Erbe, A.: Revealing the role of anchoring groups in the electrical conduction through single-molecule junctions. Small 6(14), 1529–1535 (2010)
Koepf, M., Koenigsmann, C., Ding, W., Batra, A., Negre, C.F., Venkataraman, L., Crabtree, R.H.: Controlling the rectification properties of molecular junctions through molecule–electrode coupling. Nanoscale 8(36), 16357–16362 (2016)
Ulrich, J., Esrail, D., Pontius, W., Venkataraman, L., Millar, D., Doerrer, L.H.: Variability of conductance in molecular junctions. J. Phys. Chem. B 110(6), 2462–2466 (2006)
Jamali, M.F., Tagani, M.B., Soleimani, H.R.: Improvement of the thermoelectric efficiency of Pyrene-based molecular junction with doping engineering. Chin. Phys. B 26(12), 123101 (2017)
Xue, Y., Ratner, M.A.: End group effect on electrical transport through individual molecules: a microscopic study. Phys. Rev. B 69(8), 085403 (2004)
Kim, Y., Hellmuth, T.J., Burkle, M., Pauly, F., Scheer, E.: Characteristics of amine-ended and thiol-ended alkane single-molecule junctions revealed by inelastic electron tunneling spectroscopy. ACS Nano 5(5), 4104–4111 (2011)
Kushmerick, J.G., Whitaker, C.M., Pollack, S.K., Schull, T.L., Shashidhar, R.: Tuning current rectification across molecular junctions. Nanotechnology 15(7), S489 (2004)
Van Dyck, C., Ratner, M.A.: Molecular rectifiers: a new design based on asymmetric anchoring moieties. Nano Lett. 15(3), 1577–1584 (2015)
Bala, S., Aithal, R.K., Derosa, P., Janes, D., Kuila, D.: Molecular rectifying diodes based on an aluminum/4′-hydroxy-4-biphenyl carboxylic acid/p+-silicon junction. J. Phys. Chem. C 114(48), 20877–20884 (2010)
Metzger, R.M.: Unimolecular rectifiers: present status. Chem. Phys. 326(1), 176–187 (2006)
Nijhuis, C.A., Reus, W.F., Whitesides, G.M.: Molecular rectification in metal–SAM–metal oxide–metal junctions. J. Am. Chem. Soc. 131(49), 17814–17827 (2009)
Nijhuis, C.A., Reus, W.F., Barber, J.R., Dickey, M.D., Whitesides, G.M.: Charge transport and rectification in arrays of SAM-based tunneling junctions. Nano Lett. 10(9), 3611–3619 (2010)
Souto, M., Yuan, L., Morales, D.C., Jiang, L., Ratera, I., Nijhuis, C.A., Veciana, J.: Tuning the rectification ratio by changing the electronic nature (open-shell and closed-shell) in donor–acceptor self-assembled monolayers. J. Am. Chem. Soc. 139(12), 4262–4265 (2017)
Ryu, T., Lansac, Y., Jang, Y.H.: Shuttlecock-shaped molecular rectifier: asymmetric electron transport coupled with controlled molecular motion. Nano Lett. 17(7), 4061–4066 (2017)
Metzger, R.M.: Unimolecular electronics. Chem. Rev. 115(11), 5056–5115 (2015)
Metzger, R.M.: Unimolecular electronics. J. Mater. Chem. 18(37), 4364–4396 (2008)
Metzger, R.M.: Unimolecular electrical rectifiers. Chem. Rev. 103(9), 3803–3834 (2003)
Stadler, R., Geskin, V., Cornil, J.: A theoretical view of unimolecular rectification. J. Phys. Condens. Matter 20(37), 374105 (2008)
Zahedi, E., Pangh, A.: Current–voltage characteristics through dithienylcyclopentene: a NEGF-DFT study. Phys. E 61, 1–8 (2014)
Stefani, D., Gutiérrez-Cerón, C.A., Aravena, D., Labra-Muñoz, J., Suarez, C., Liu, S., Dulic, D.: Charge transport through a single molecule of trans-1-bis-Diazofluorene [60] fullerene. Chem. Mater. 29(17), 7305–7312 (2017)
Sebera, J., Kolivoska, V., Valášek, M., Gasior, J., Sokolová, R., Meszaros, G., Hromadová, M.: Tuning charge transport properties of asymmetric molecular junctions. J. Phys. Chem. C 121(23), 12885–12894 (2017)
Wang, L.H., Guo, Y., Tian, C.F., Song, X.P., Ding, B.J.: Negative differential resistance and rectifying behaviors in atomic molecular device with different anchoring groups. Phys. E 43(1), 524–528 (2010)
Zhang, H., Zeng, J., Chen, K.Q.: Rectifying and negative differential resistance behaviors induced by asymmetric electrode coupling in Pyrene-based molecular device. Phys. E 44(7), 1631–1635 (2012)
Fan, Z.Q., Zhang, Z.H., Qiu, M., Deng, X.Q., Tang, G.P.: The site effects of B or N doping on IV characteristics of a single Pyrene molecular device. Appl. Phys. Lett. 101(7), 073104 (2012)
Brandbyge, M., Mozos, J.L., Ordejón, P., Taylor, J., Stokbro, K.: Density-functional method for nonequilibrium electron transport. Phys. Rev. B 65(16), 165401 (2002)
Zhang, Z., Yang, Z., Yuan, J., Zhang, H., Ming, Q., Deng, X.: Electronic transport properties of pheny1 based molecular devices. Solid State Commun. 149(1), 60–63 (2009)
Liu, J., Kind, M., Schüpbach, B., Käfer, D., Winkler, S., Zhang, W., Wöll, C.: Triptycene-terminated thiolate and selenolate monolayers on Au (111). Beilstein J. Nanotechnol. 8, 892 (2017)
Lud, S.Q., Neppl, S., Richter, G., Bruno, P., Gruen, D.M., Jordan, R., Garrido, J.A.: Controlling surface functionality through generation of thiol groups in a self-assembled monolayer. Langmuir 26(20), 15895–15900 (2010)
Rangel, T., Ferretti, A., Olevano, V., Rignanese, G.M.: Many-body correlations and coupling in benzene-dithiol junctions. Phys. Rev. B 95(11), 115137 (2017)
Kristensen, I.S., Mowbray, D.J., Thygesen, K.S., Jacobsen, K.W.: Comparative study of anchoring groups for molecular electronics: structure and conductance of Au–S–Au and Au–NH2–Au junctions. J. Phys. Condens. Matter 20(37), 374101 (2008)
Ford, M.J., Hoft, R.C., McDonagh, A.M., Cortie, M.B.: Rectification in donor–acceptor molecular junctions. J. Phys. Condens. Matter 20(37), 374106 (2008)
Mishchenko, A., Zotti, L.A., Vonlanthen, D., Bürkle, M., Pauly, F., Cuevas, J.C., Wandlowski, T.: Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group. J. Am. Chem. Soc. 133(2), 184–187 (2010)
Nigam, S., Sahoo, S.K., Sarkar, P., Majumder, C.: Chair like NiAu6: clusters assemblies and CO oxidation study by ab initio methods. Chem. Phys. Lett. 584, 108–112 (2013)
Ganji, M.D.: Azopyridine molecular conductor: a superior device for molecular switch technology. Electron. Mater. Lett. 8(6), 565–570 (2012)
Quek, S.Y., Venkataraman, L., Choi, H.J., Louie, S.G., Hybertsen, M.S., Neaton, J.B.: Amine–gold linked single-molecule circuits: experiment and theory. Nano Lett. 7(11), 3477–3482 (2007)
Paulsson, M., Frederiksen, T., Brandbyge, M.: Inelastic transport through molecules: comparing first-principles calculations to experiments. Nano Lett. 6(2), 258–262 (2006)
Perdew, J.P., Burke, K., Ernzerhof, M.: Generalized gradient approximation made simple. Phys. Rev. Lett. 77(18), 3865 (1996)
Datta, S.: Electronic transport in mesoscopic systems. Cambridge University Press, Cambridge (1997)
Büttiker, M., Imry, Y., Landauer, R., Pinhas, S.: Generalized many-channel conductance formula with application to small rings. Phys. Rev. B 31(10), 6207 (1985)
Fan, Z.Q., Zhang, Z.H., Deng, X.Q., Tang, G.P., Yang, C.H., Sun, L., Zhu, H.L.: Effect of electrode twisting on electronic transport properties of atomic carbon wires. Carbon 98, 179–186 (2016)
Huisman, E.H., Guédon, C.M., van Wees, B.J., van der Molen, S.J.: Interpretation of transition voltage spectroscopy. Nano Lett. 9(11), 3909–3913 (2009)
Chen, X., Braunschweig, A.B., Wiester, M.J., Yeganeh, S., Ratner, M.A., Mirkin, C.A.: Spectroscopic tracking of molecular transport junctions generated by using click chemistry. Angew. Chem. Int. Ed. 48(28), 5178–5181 (2009)
Podstawka, E., Ozaki, Y., Proniewicz, L.M.: Part III: surface-enhanced Raman scattering of amino acids and their homodipeptide monolayers deposited onto colloidal gold surface. Appl. Spectrosc. 59(12), 1516–1526 (2005)
Chen, F., Li, X., Hihath, J., Huang, Z., Tao, N.: Effect of anchoring groups on single-molecule conductance: comparative study of thiol-, amine-, and carboxylic-acid-terminated molecules. J. Am. Chem. Soc. 128(49), 15874–15881 (2006)
Acknowledgements
This work was supported by Iran National Science Foundation (INSF) (94011986).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Jamali, M.F., Soleimani, H.R. & Tagani, M.B. The maximum rectification ratio of pyrene-based molecular devices: a systematic study. J Comput Electron 18, 453–464 (2019). https://doi.org/10.1007/s10825-019-01307-5
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10825-019-01307-5