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

References

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