Structure-property relationships of curved aromatic materials from first principles

Accounts of Chemical Research

Volumn 47, Issue 11, 2014, Pages 3310-3320

  Zoppi, Laura ^a   Martin Samos, Layla ^b,c   Baldridge, Kim K ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF NOVA GORICA   (Slovenia)

^c IOM CNR LABORATORIO TASC   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84911095862     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5001132     Document Type: Article

References (77)

1. Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Highly efficient organic light-emitting diodes from delayed fluorescence Nature 2012, 492, 234-240
2. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Santos, D. A. D.; Brédas, J. L.; Lögdlund, M. Electroluminescence in conjugated polymers Nature 1999, 397, 121-128
3. Scharber, M. C.; Wuhlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. L. Design rules for donors in bulk-heterojunction solar cells-towards 10% energy-conversion efficiency Adv. Mater. 2006, 18, 789-794
4. Forrest, S. R. The path to ubiquitous and low-cost organic electronic appliances on plastic Nature 2004, 428, 911-918
5. Hohenberg, P.; Kohn, W. Inhomogeneous electron gas Phys. Rev. 1964, 136, B864-B871
6. Kohn, W.; Sham, L. Self-consistent equations including exchange and correlation effects Phys. Rev. 1965, 140, A1133-A1138
7. Dreizler, R. M.; Eberhard, E. K.; Gross, K. U. Density Functional Theory: An Approach to the Quantum Many- Body Problem; Springer-Verlag: Berlin, 1990.
8. Grimme, S.; Antony, J.; Schwabe, T.; Mück-Lichtenfeld, C. Density functional theory with dispersion corrections for supramolecular structures, aggregates, and complexes of (bio)organic molecules Org. Biomol. Chem. 2007, 5, 741-758
9. Antony, J.; Brüske, B.; Grimme, S. Cooperativity in noncovalent interactions of biologically relevant molecules Phys. Chem. Chem. Phys. 2009, 11, 8440-8447
10. Dion, M.; Rydberg, H.; Schröder, E.; Langreth, D. C.; Lundqvist, B. I. Van der Waals density functional for general geometries Phys. Rev. Lett. 2004, 92 246401
11. McNellis, E. E.; Meyer, J.; Reuter, K. Azobenzene at coinage metal surfaces: Role of dispersive van der Waals interactions Phys. Rev. B 2009, 80 205414
12. 4 on the Cu(110) Surface Phys. Rev. Lett. 2009, 102 136809
13. Onida, G.; Reining, L.; Rubio, A. Electronic excitations: Density-functional versus Many-Body Green's-function approaches Rev. Mod. Phys. 2002, 74, 601-659
14. Rostgaard, C.; Jacobsen, K. W.; Thygesen, K. S. Fully self-consistent GW calculations for molecules Phys. Rev. B 2010, 81 085103
15. Kaasbjerg, K.; Thygesen, K. S. Benchmarking GW against exact diagonalization for semiempirical models Phys. Rev. B 2010, 81 085102
16. Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Challenges for density functional theory Chem. Rev. 2012, 112, 289-320
17. Rohlfing, M.; Louie, S. G. Electron-hole excitations and optical spectra from first principles Phys. Rev. B 2000, 62, 4927-4943
18. Duchemin, I.; Blase, X. Resonant hot charge-transfer excitations in fullerene-porphyrin complexes: Many-Body Bethe-Salpeter study Phys. Rev. B 2013, 87 245412
19. Baumeier, B.; Andrienko, D.; Rohlfing, M. Frenkel and charge-transfer excitations in donor-acceptor complexes from Many-Body Green's functions theory J. Chem. Theory Comput. 2012, 8, 2790-2795
20. Difley, S.; Voorhis, T. V. Exciton/charge-transfer electronic couplings in organic semiconductors J. Chem. Theory Comput. 2011, 7, 594-601
21. Zoppi, L.; Siegel, J. S.; Baldridge, K. K. Electron transport and optical properties of curved aromatics Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2013, 3, 1-12
22. Zoppi, L.; Martin-Samos, L.; Baldridge, K. K. Effect of molecular packing on corannulene-based materials electroluminescence J. Am. Chem. Soc. 2011, 133, 14002-14009
23. Bauert, T.; Zoppi, L.; Koller, G.; Siegel, J. S.; Baldridge, K. K.; Ernst, K.-H. Quadruple anionic buckybowls by solid-state chemistry of corannulene and cesium J. Am. Chem. Soc. 2013, 135, 12857-12860
24. Merz, L.; Parschau, M.; Zoppi, L.; Baldridge, K. K.; Siegel, J. S.; Ernst, K. H. Reversible phase transitions in a buckybowl monolayer Angew. Chem., Int. Ed. 2009, 48, 1966-1969
25. Song, H.; Reed, M. A.; Lee, T. Single molecule electronic devices Adv. Mater. 2011, 23, 1583-1608
26. Feng, M.; Zhao, J.; Petek, H. Atomlike, hollow-core-bound molecular orbitals of C60 Science 2008, 320, 359-362
27. Zhao, J.; Feng, M.; Yang, J. L.; Petek, H. The superatom states of fullerenes and their hybridization into the nearly free electron bands of fullerites ACS Nano 2009, 3, 853-864
28. Feng, M.; Zhao, J.; Huang, T.; Zhu, X.; Petek, H. The electronic properties of superatom states of hollow molecules Acc. Chem. Res. 2011, 44, 360-368
29. Silkin, V. M.; Zhao, J.; Guinea, F.; Chulkov, E. V.; Echenique, P. M.; Petek, H. Image potential states in graphene Phys. Rev. B 2009, 80 121408
30. Borchardt, l.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. Synthesis and dynamics of the corannulene nucleus J. Am. Chem. Soc. 1992, 114, 1921-1923
31. Lovas, F. J.; McMahon, R. J.; Grabow, J.-U.; Schnell, M.; Mack, J.; Scott, L. T.; Kuczkowski, R. L. Interstellar chemistry: A strategy for detecting polycyclic aromatic hydrocarbons in space J. Am. Chem. Soc. 2005, 127, 4345-4349
32. Zoppi, L.; Ferretti, A.; Baldridge, K. K. Static and field-oriented properties of bowl-shaped polynuclear aromatic hydrocarbon fragments J. Chem. Theory Comput. 2013, 9, 4797-4804
33. Wu, Y.-T.; Bandera, D.; Maag, R.; Linden, A.; Baldridge, K. K.; Siegel, J. S. Multi-ethynyl corannulenes: Synthesis, structure and properties J. Am. Chem. Soc. 2008, 130, 10729-10739
34. Parschau, M.; Fasel, R.; Ernst, K.-H.; Gröning, O.; Brandenberger, L.; Schillinger, R.; Greber, T.; Seitsonen, A. P.; Wu, Y.-T.; Siegel, J. S. Buckybowls on metal surfaces: Symmetry mismatch and enantiomorphism of corannulene on Cu(110) Angew. Chem., Int. Ed. 2007, 46, 8258-8261
35. http://qe-forge.org/gf/project/q-e/.
36. Hedin, L. New method for calculating the one-particle Green's function with application to the electron-gas problem Phys. Rev. 1965, 139, A796-A823
37. Hedin, L.; Lundqvist, S. Effects of Electron-Electron and Electron-Phonon Interactions on the One-electron States in Solids; Ehrenreich, H.; Seitz, F.; Turnbull, D., Eds.; Solid State Physics: Advances in research and Applications, Vol. 23, Academic: New York, 1969.
38. Martin-Samos, L.; Bussi, G. Comp. Phys. Comm. 2009, 180, 1416-1425
39. Fetter, A. L.; Walecka, J. D. Quantum Theory of Many-Particle Systems; McGraw-Hill: New York, 1971.
40. Hüser, F.; Olsen, T.; Thygesen, K. S. Quasiparticle GW calculations for solids, molecules, and two-dimensional materials Phys. Rev. B 2013, 87 235132
41. Bauert, T.; Zoppi, L.; Koller, G.; Garcia, A.; Baldridge, K. K.; Ernst, K.-H. Large interface dipole moments without charge transfer: buckybowls on metal surfaces J. Phys. Chem. Lett. 2011, 2, 2805-2809
42. Scholes, G. D.; Rumbles, G. Excitons in nanoscale systems Nat. Mater. 2006, 683-696
43. Barford, W. Theory of singlet exciton yield in light-emitting polymers Phys. Rev. B 2004, 70 205204
44. Rocca, D.; Lu, D.; Galli, G. Ab initio calculations of optical absorption spectra: Solution of the Bethe-Salpeter equation within density matrix perturbation theory J. Chem. Phys. 2010, 133, 164109
45. Kaduk, B.; Kowalczyk, T.; Voorhis, T. V. Constrained density functional theory Chem. Rev. 2012, 112, 321-370
46. Wu, Q.; Voorhis, T. V. Constrained density functional theory and its application in long-range electron transfer J. Chem. Theory Comput. 2006, 2, 765-774
47. Yost, S. R.; Wang, L. P.; Voorhis, T. V. Molecular Insight Into the Energy Levels at the Organic Donor/Acceptor Interface: A Quantum Mechanics/Molecular Mechanics Study J. Phys. Chem. C 2011, 115, 14431-14436
48. Marques, M. A. L.; Ulrich, C. A.; Nogueira, F.; Rubio, A.; Burke, K.; Gross, E. K. U., Time Dependent Density Functional Theory Lecture Notes in Physics 706; Springer: Berlin, 2006.
49. Casida, M. E. Time-dependent density-functional theory for molecules and molecular solids J. Mol. Struct.: THEOCHEM 2009, 914, 3-18
50. Albrecht, S.; Reining, L.; Sole, R. D.; Onida, G. Ab initio calculation of excitonic effects in the optical spectra of semiconductors Phys. Rev. Lett. 1998, 80, 4510-4515
51. Hummer, K.; Ambrosch-Draxl, C. Oligoacene exciton binding energies: Their dependence on molecular size Phys. Rev. B 2005, 71 081202(R)
52. Bruno, M.; Palummo, M.; Marini, A.; Sole, R. D.; Olevano, V.; Kholod, A. N.; Ossicini, S. Excitons in germanium nanowires: Quantum confinement, orientation, and anisotropy effects within a first-principles approach Phys. Rev. B 2005, 72 153310
53. Rohlfing, M.; Louie, S. G. Electron-hole excitations in semiconductors and insulators Phys. Rev. Lett. 1998, 81, 2312-2315
54. Rohlfing, M.; Louie, S. G. Optical excitations in conjugated polymers Phys. Rev. Lett. 1999, 82, 1959-1962
55. Tiago, M. L.; Rohlfing, M.; Louie, S. G. Bound excitons and optical properties of bulk trans-polyacetylene Phys. Rev. B 2004, 70 193204
56. Ferretti, A.; Mallia, G.; Martin-Samos, L.; Bussi, G. i.; Ruini, A.; Montanari, B.; Harrison, N. M. Ab initio complex band structure of conjugated polymers: Effects of hydrid density functional theory and GW schemes Phys. Rev. B 2012, 85 235105
57. Tiago, M. L.; Northrup, J. E.; Louie, S. G. Ab initio calculation of the electronic and optical properties of solid pentacene Phys. Rev. B 2003, 67 115212
58. Sharifzadeh, S.; Biller, A.; Kronik, L.; Neaton, J. B. Quasiparticle and optical spectroscopy of the organic semiconductors pentacene and PTCDA from first principles Phys. Rev. B 2012, 85 125307
59. Sharifzadeh, S.; Darancet, P.; Kronik, L.; Neaton, J. B. Low-energy charge-transfer excitons in organic solids from first-principles: The case of pentacene J. Phys. Chem. Lett. 2013, 4, 2197-2201
60. Ambrosch-Draxl, C.; Nabok, D.; Puschnig, P.; Meisenbichler, C. The role of polymorphism in organic thin films: oligoacenes investigated from first principles New J. Phys. 2009, 11 125010
61. Neaton, J. B.; Hybertsen, M. S.; Louie, S. G. Renormalization of molecular electronic levels at metal-molecule interfaces Phys. Rev. Lett. 2006, 97 216405
62. Cahen, D.; Kahn, A. Electron energetics at surfaces and interfaces: Concepts and experiments Adv. Mater. 2003, 15, 271-277
63. Witte, G.; Lukas, S.; Bagus, P. S.; Wöll, C. Vacuum level alignment at organic/metal junctions: 'Cushion' effect and the interface dipole Appl. Phys. Lett. 2005, 87 263502
64. Li, G.; Tamblyn, I.; Cooper, V. R.; Gao, H.-J.; Neaton, J. B. Molecular adsorption on metal surfaces with van der Waals density functionals Phys. Rev. B 2012, 85 121409
65. Grimme, S. J. Semiempirical GGA-type density functional constructed with a long-range dispersion correction J. Comput. Chem. 2006, 27, 1787-1799
66. Aradhya, S. V.; Frei, M.; Hybertsen, M. S.; Venkataraman, L. Van der Waals interactions at metal/organic interfaces at the single-molecule level Nat. Mater. 2012, 11, 872-876
67. Shi, X.-Q.; Li, Y.; Hove, M. A. V.; Zhang, R.-Q. Interactions between organics and metal surfaces in the intermediate regime between physisorption and chemisorption J. Phys. Chem. C 2012, 116, 23603-23607
68. Soler, J. M.; Artacho, E.; Gale, D. J.; Garcia, A.; Junquera, J.; Ordejon, P.; Sanchez-Portal, D. The SIESTA method for ab initio order-N materials simulation J. Phys.: Condens. Matter 2002, 14, 2745-2779
69. Zoppi, L.; Garcia, A.; Baldridge, K. K. Development of methods for computational analysis of the binding of molecules on metallic surfaces: Application to corannulene on copper surface J. Phys. Chem. A 2010, 114, 8864-8872
70. Romaner, L.; Heimel, G.; Ambrosch-Draxl, C.; Zojer, E. The dielectric constant of self-assembled monolayers Adv. Funct. Mater. 2008, 18, 3999-4006
71. Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Conductance of a molecular junction Science 1997, 278, 252-254
72. Seiders, T. J.; Baldridge, K. K.; Grube, G. H.; Siegel, J. S. Structure/energy correlation of bowl depth and inversion barrier in corannulene derivatives: combined experimental, and quantum mechanical analysis J. Am. Chem. Soc. 2001, 123, 517-525
73. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, M.; Nguyen, K. A.; Su, S.; Windus, T. L.; Elbert, S. T. General atomic and molecular electronic structure system J. Comput. Chem. 1993, 14, 1347-1363
74. Guédon, C. M.; Valkenier, H.; Markussen, T.; Thygesen, K. S.; Hummelen, J. C.; Molen, S. J. v. d. Observation of quantum interference in molecular charge transport Nat. Nanotechnol. 2012, 7, 305-309
75. Vazquez, H.; Skouta, R.; Schneebeli, S.; Kamenetska, M.; Breslow, R.; Venkataraman, L.; Hybertsen, M. S. Probing the conductance superposition law in single-molecule circuits with parallel paths Nat. Nanotechnol. 2012, 7, 663-667
76. Aradhya, S. V.; Venkataraman, L. Single-molecule junctions beyond electronic transport Nat. Nanotechnol. 2013, 8, 399-410
77. Congreve, D. l. N.; Lee, J.; Thompson, N. J.; Hontz, E.; Yost, S. R.; Reusswig, P. D.; Bahlke, M. E.; Reineke, S.; Voorhis, T. V.; Baldo, M. A. External quantum efficiency above 100% in a singlet-exciton-fission-based organic photovoltaic cell Science 2013, 340, 334-337