Comparative parametric method 6 (PM6) and Recife model 1 (RM1) study of trans -stilbene

Molecular Simulation

Volumn 38, Issue 1, 2012, Pages 1-7

  Camilo, A ^a   Dos Santos, R P B ^b,c   Coluci, V R ^c   Galvao D S ^c  

^a STATE UNIVERSITY OF PONTA GROSSA   (Brazil)

^b STATE UNIVERSITY OF MARINGÁ   (Brazil)

^c UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

PM6; RM1; semi empirical methods; trans stilbene

Indexed keywords

AB INITIO METHOD; AUSTIN MODEL 1; BIPOLARONS; CIS-TRANS ISOMERISATION; EXPERIMENTAL DATA; PARAMETRIC METHOD; PLANAR CONFIGURATIONS; PM6; RM1; SEMI-EMPIRICAL; SEMI-EMPIRICAL METHODS; SINGLET STATE; TRANS-STILBENE;

CONDENSED MATTER PHYSICS;

MOLECULAR STRUCTURE;

EID: 84857208715     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927022.2011.597392     Document Type: Article

References (51)

1. E. Hückel, Quantum-theoretical contributions to the benzene problem. I. The electron configuration of benzene and related compounds, Z. Phys. 70 (1931), pp. 204-286.
2. D.B. Boyd, Evidence that there is a future for semiempirical molecular orbital calculations, J. Mol. Struct. (Theochem) 401 (1997), pp. 219-225. (Pubitemid 127397173)
3. T. Clark, Quo Vadis semiempirical MO-theory? J. Mol. Struct. (Theochem) 530 (2000), pp. 1-10.
4. G.B. Rocha, R.O. Freire, A.M. Simas, and J.J.P. Stewart, RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I, J. Comp. Chem. 27 (2006), pp. 1101-1111. (Pubitemid 43989803)
5. J.J.P. Stewart, Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements, J. Mol. Mod. 13 (2007), pp. 1173-1213. (Pubitemid 47629446)
6. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Bums, and A.B. Holmes, Lightemitting- diodes based on conjugated polymers, Nature 347 (1990), pp. 539-541. (Pubitemid 120015057)
7. I. Benjamin, E.Z. Faraggi, Y. Avny, D. Davidov, and R. Neumann, Fluorinated poly(p-phenylenevinylene) copolymers: Preparation and use in light-emitting diodes, Chem. Mater. 8 (1996), pp. 352-355. (Pubitemid 126468854)
8. E.Z. Faraggi, G. Cohen, R. Neumann, Y. Avny, and D. Davidov, Spectral tuning of electroluminescence in conjugated copolymers by application of an external electric field, Adv. Mater. 8 (1996), pp. 234-237. (Pubitemid 126697172)
9. M. Granstrom and O. Inganas, White light emission from a polymer blend light emitting diode, Appl. Phys. Lett. 68 (1996), pp. 147-149. (Pubitemid 126683987)
10. R.M. Gurge, A. Sarker, and P.M. Lahti, Red light emitting "pushpull" disubstituted poly(1,4-phenylenevinylenes), Macromolecules 29 (1996), pp. 4287-4292. (Pubitemid 126634331)
11. M.A. Diaz Garcia, F. Hide, B.J. Schwartz, M.R. Anderson, Q.B. Pei, and A.J. Heeger, Plastic lasers: Semiconducting polymers as a new class of solid-state laser materials, Synth. Met. 84 (1997), pp. 455-462. (Pubitemid 127401471)
12. U. Lemmer, R. Henning, and W. Guss, Microcavity effects in a spincoated polymer 2-layer system, Appl. Phys. Lett. 66(11) (1995), pp. 1301-1303.
13. N. Yessler, G.J. Denton, and R.H. Friend, Lasing from conjugatedpolymer microcavities, Nature 382(22) (1996), pp. 695-697.
14. Y. Cao, G. Yu, and A.J. Heeger, Efficient, low operating voltage polymer light-emitting diodes with aluminum as the cathode material, Adv. Mater. 10 (1998), pp. 917-920.
15. S. Son, A. Dodabalapur, A.J. Lovinger, and M.E. Galvin, Luminescence enhancement by the introduction of disorder into poly(p-phenylene vinylene), Science 269 (1995), pp. 376-378.
16. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Burns, and A.B. Holmes, Lightemitting- diodes based on conjugated polymers, Nature 347 (1990), pp. 539-541. (Pubitemid 120015057)
17. P.L. Burn, A.B. Holmes, A. Kraft, D.D.C. Bradley, A.R. Brown, R.H. Friend, and R.W. Gymer, Chemical tuning of electroluminescent copolymers to improve emission efficiencies and allow patterning, Nature 356 (1992), pp. 47-49. (Pubitemid 23565586)
18. N.C. Greenham, S.C. Moratti, D.D.C. Bradley, R.H. Friend, and A.B. Holmes, Efficient light-emitting-diodes based on polymers with high electron-affinities, Nature 365 (1993), pp. 628-630.
19. D.S. Galvão, Z.G. Soos, S. Ramasesha, and S. Etemad, A parametric method-3 (pm3) study of trans-stilbene, J. Chem. Phys. 98(4) (1993), pp. 3016-3021.
20. R. Vendrame, V.R. Coluci, and D.S. Galvão, Comparative parametric method 5 (PM5) study of trans-stilbene, J. Mol. Struct. (Theochem) 686 (2004), pp. 103-108.
21. A. Hoekstra, P. Meertens, and A. Vos, Refinement of crystalstructure of trans-stilbene (TSB) - molecular-structure in crystalline and gaseous phases, Acta Crystallogr. Sect. B 31 (1975), pp. 2813-2817.
22. J. Bernstein, Refinement of trans-stilbene - comparison of 2 crystallographic studies, Acta Crystallogr. Sect. B 31 (1975), pp. 1268-1271.
23. M. Traetteberg, E.G. Frantsen, F.C. Mijhoff, and A. Hoekstra, Gas electron-diffraction study of molecular-structure of transstilbene, J. Mol. Struct. 26 (1975), pp. 57-68.
24. W.Y. Chiang and J. Laane, Fluorescence-spectra and torsional potential functions for trans-stilbene in its s-0 and s-1(pi,pi(asterisk)) electronic states, J. Chem. Phys. 100 (1994), pp. 8755-8767.
25. D.H. Waldeck, Photoisomerization dynamics of stilbenes, Chem. Rev. 91 (1991), pp. 415-436 (and references therein).
26. B.B. Champagne, J.F. Pfanstiel, D.F. Plusquellic, D.W. Pratt, W.M. van Herpen, and W.L. Meerts, Trans-stilbene - a rigid, planar asymmetric-top in the zero-point vibrational levels of its S0 and S1 electronic states, J. Phys. Chem. 94 (1990), pp. 6-8.
27. L.H. Spangler, R. van Zee, and T.S. Zwier, Assignment of the lowfrequency modes in trans-stilbene - evidence for planarity in the isolated molecule, J. Phys. Chem. 91 (1987), pp. 2782-2786.
28. T.M. Stachelek, T.A. Pazoha, W.M. McClain, and R.D. Drucker, Detection and assignment of phantom photochemical singlet of trans-stilbene by 2-photon excitation, J. Chem. Phys. 66 (1977), pp. 4540-4543.
29. B.I. Greene, R.M. Hochstrasser, and R.B. Weisman, Spectroscopic study of the picosecond photoisomerization of stilbene, Chem. Phys. Lett. 62 (1979), pp. 427-430.
30. S.P. Kwasniewski, L. Claes, J.-P. Francois, and M.S. Deleuze, High level theoretical study of the structure and rotational barriers of trans-stilbene, J. Chem. Phys. 118 (2003), pp. 7823-7836.
31. J. Catalan, On the non-planarity of trans-stilbene, Chem. Phys. Lett. 421 (2006), pp. 134-137.
32. P.D. Chowdary, T.J. Martinez, and M. Gruebele, The vibrationally adiabatic torsional potential energy surface of trans-stilbene, Chem. Phys. Lett. 440 (2007), pp. 7-11. (Pubitemid 46693719)
33. N.L. Allinger and U. Burkert, Molecular Mechanics, American Chemical Society, Washington, DC, 1982.
34. R.G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
35. J.P. Stewart, Computational Chemistry, Version 7.101W, Mopac 2007. Available at http://openmopac.net
36. J.H. Simpson, D.M. Rice, and F.E. Karask, Investigation of h2so4- doped, ring-deuterated poly(para-phenylene vinylene) using solidstate H-2 quadrupole echo NMR-spectroscopy, Polymer 32 (1991), pp. 2340-2344.
37. J.H. Simpson, N. Egger, M.A. Masse, D.M. Rice, and F.E. Karasz, Solid-state C-13 NMR characterization of annealed poly( pphenylene vinylene) PPV films, J. Pol. Sci. B 28 (1990), pp. 1859-1869. (Pubitemid 20723436)
38. L. Claes, S. Kwasniewski, M.S. Deleuze, and J.-P. Francois, Comparative study of the molecular structure of stilbene using molecular mechanics, Hartree-Fock, and density functional theories, J. Mol. Struct. (Theochem) 549 (2001), pp. 63-67. (Pubitemid 32705834)
39. N.L. Allinger, Y. Yuh, and J.H. Lii, Molecular mechanics - the MM3 force-field for hydrocarbons. 1, J. Am. Chem. Soc. 111 (1989), pp. 8551-8566. (Pubitemid 20021795)
40. J.H. Lii and N.L. Allinger, Molecular mechanics - the MM3 force-field for hydrocarbons. 2. Vibrational frequencies and thermodynamics, J. Am. Chem. Soc. 111 (1989), pp. 8566-8575. (Pubitemid 20021796)
41. J.H. Lii and N.L. Allinger, Molecular mechanics - the MM3 force-field for hydrocarbons. 3. The Vanderwaals potentials and crystal data for aliphatic and aromatic-hydrocarbons, J. Am. Chem. Soc. 111 (1989), pp. 8576-8582. (Pubitemid 20021797)
42. R. Ditchfield, W.J. Hehre, and J.A. Pople, Self-consistent molecular-orbital methods. 9. Extended Gaussian-type basis for molecular-orbital studies of organic molecules, J. Chem. Phys. 54 (1971), pp. 724-728.
43. W.J. Hehre, R. Ditchfield, and J.A. Pople, Self-consistent molecular-orbital methods. 12. Further extensions of Gaussiantype basis sets for use in molecular-orbital studies of organicmolecules, J. Chem. Phys. 56 (1972), pp. 2257-2261.
44. R.C. Binning, Jr and L.A. Curtiss, Compact contracted basis-sets for 3rd-row atoms - GA-KR, J. Comp. Chem. 11 (1990), pp. 1206-1216.
45. A.D. Becke, A new mixing of Hartree-Fock and local densityfunctional theories, J. Chem. Phys. 98 (1993), pp. 1372-1377.
46. A.D. Becke, Density-functional thermochemistry. 3. The role of exact exchange, J. Chem. Phys. 98 (1993), pp. 5648-5652.
47. C.T. Lee, W.T. Yang, and R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B 37 (1988), pp. 785-789.
48. T. Kobayashi, H. Suzuki, and K. Ogawa, Conformational-analysis of stilbenes by photo-electron spectroscopy, Bull. Chem. Soc. Jpn 55 (1982), pp. 1734-1738.
49. A. Alparone, V. Librando, and Z. Minniti, Validation of semiempirical PM6 method for the prediction of molecular properties of polycyclic aromatic hydrocarbons and fullerenes, Chem. Phys. Lett. 460 (2008), pp. 151-154.
50. J. Rezac, J. Fanfrlik, D. Salahub, and P. Hobza, Semiempirical quantum chemical PM6 method augmented by dispersion and H-bonding correction terms reliably describes various types of noncovalent complexes, J. Chem. Theory Comp. 5 (2009), pp. 1749-1760.
51. T. Puzyn, N. Suzuki, M. Haranczyk, and J. Rak, Calculation of quantum-mechanical descriptors for QSPR at the DFT level: Is it necessary? J. Chem Inf. Model. 48 (2008), pp. 1174-1180.