π-Conjugation

Wiley Interdisciplinary Reviews: Computational Molecular Science

Volumn 2, Issue 4, 2012, Pages 513-524

  Milián Medina, Begoña ^a   Gierschner, Johannes ^a  

^a INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84862546145     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.95     Document Type: Article

References (56)

1. Special issue on Organic electronics and optoelectronics. Chem Rev 2007, 107:923-1386.
2. Special issue on Materials for electronics. Chem Rev 2010, 110:1-574.
3. Special issue on Organic photovoltaics. Acc Chem Res 2009, 42:1689-1857.
4. Brédas JL, Beljonne D, Coropceanu V, Cornil J. Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers: a molecular picture. Chem Rev 2004, 104:4971-5004.
5. Beaujuge PM, Amb CM, Reynolds JR. Spectral engineering in π-conjugated polymers with intramolecular donor-acceptor interactions. Acc Chem Res 2010, 43:1396-1407.
6. Hains AW, Liang Z, Woodhouse MA, Gregg BA. Molecular semiconductors in organic photovoltaic cells. Chem Rev 2010, 110:6689-6735.
7. Zhao Y, Truhlar DG. Density functionals with broad applicability in chemistry. Acc Chem Res 2008, 41:157-167.
8. Lewis GN, Calvin M. The color of organic substances. Chem Rev 1939, 25:273-328.
9. Alabugin IV, Gilmore KM, Peterson PW. Hyperconjugation. WIREs Comput Mol Sci 2011, 1:109-141.
10. Limacher PA, Lüthi HP. Crosss-conjugation. WIREs Comput Mol Sci 2011, 1:477-486.
11. Gierschner J, Cornil J, Egelhaaf HJ. Optical bandgaps of π-conjugated organic materials at the polymer limit: experiment and theory. Adv Mater 2007, 19:173-191.
12. Wiberg KB, Nakaji DY, Morgan KM. Heat of hydrogenation of a cis imine. An experimental and theoretical study. J Am Chem Soc 1993, 115:3527-3532.
13. Chen Z, Wannere CS, Corminboeuf C, Puchta R, Schleyer PvR. Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. Chem Rev 2005, 105:3842-3888.
14. Shaik S, Hiberty PC. A primer on qualitative valence bond theory-A theory coming of age. WIREs Comput Mol Sci 2011, 1:18-29.
15. Heilbronner E, Bock H. The HMO-Model and its Application. Weinheim, Germany: VCH, GmbH; 1976.
16. Pariser R. Theory of the electronic spectra and structure of the polyacenes and of alternant hydrocarbons. J Chem Phys 1956, 24:250-268.
17. Kutzelnigg W. What i like about Hückel theory. J Comput Chem 2007, 28:25-34.
18. Dewar MJS, Longuet-Higgins HC. The correspondence between the resonance and molecular orbital theories. Proc Roy Soc London A 1952, 214:482-493.
19. Woodward RB, Hoffmann R. Stereochemistry of electrocyclic reactions. J Am Chem Soc 1965, 87:395-397.
20. Milián-Medina B, Beljonne D, Egelhaaf HJ, Gierschner J. Effect of fluorination on the electronic structure and optical excitations of π-conjugated molecules. J Chem Phys 2007, 126:111101/1-111101/6.
21. Minkin VI, Glukhovtsev MN, Simkin, BY. Aromaticity and Antiaromaticity. New York: Wiley; 1994.
22. Kertesz M, Choi CH, Yang S. Conjugated polymers and aromaticity. Chem Rev 2005, 105:3448-3481.
23. Zielinski M, Havenith RWA, Jenneskens LW, van Lenthe JH. A comparison of approaches to estimate the resonance energy. Theor Chem Acc 2010, 127:19-25.
24. Mo Y, Hiberty PC, von Ragué Schleyer P. How to properly compute the resonance energy within the ab initio valence bond theory: a response to the ZHJVL paper. Theor Chem Acc 2010, 127:27-38.
25. Sancho-García JC, Pérez-Jiménez AJ. Improved accuracy with medium cost computational methods for the evaluation of bond length alternation of increasingly long oligoacetylenes. Phys Chem Chem Phys 2007, 9:5874-5879.
26. x. Application of the intermediate exciton formalism. Chem Phys 1979, 44:349-356.
27. Casado J, Miller LL, Mann KR, Pappenfus TM, Higuchi H, Ortí E, Milián B, Pou-Amérigo R, Hernández V, López Navarrete JT. Quinonoid oligothiophenes as electron-donor and electron-acceptor materials. A spectroelectrochemical and theoretical study. J Am Chem Soc 2002, 124:12380-12388.
28. Tavan P, Schulten K. Electronic excitations in finite and infinite polyenes. Phys Rev B 1987, 36:4337-4358.
29. Gierschner J, Mack HG, Lüer L, Oelkrug D. Fluorescence and absorption spectra of oligophenylenevinylenes: vibronic coupling, band shapes and solvatochromism. J Chem Phys 2002, 116:8596-8609.
30. Jacquemin D, Adamo C. Bond length alternation of conjugated oligomers: wave function and DFT benchmarks. J Chem Theory Comput 2011, 7:369-376.
31. Hoeckstra A, Meerteens P, Vos A. Refinement of the crystal structure of trans-stilbene (TSB). The molecular structure in the crystalline and gaseous phases. Acta Crystallogr Sect B 1975, 31:2813-2817.
32. 12. Acta Crystallogr Sect C 1984, 40:428-431.
33. Choi CH, Kertesz M. Conformational information from vibrational spectra of styrene, trans-stilbene, and cis-stilbene. J Phys Chem A 1997, 101:3823-3831.
34. Galvao DS, Soos ZG, Ramasesha S, Eternad S. A parametric method 3 (PM3) study of trans-stilbene. J Chem Phys 1993, 98:3016-3021.
35. U states of trans-stilbene. J Phys Chem A 2002, 106:7355-7361.
36. Kwasniewski SP, Claes L, François J-P, Deleuze MS. High level theoretical study of the structure and rotational barriers of trans-stilbene. J Chem Phys 2003, 118:7823-7836.
37. Ogawa K, Harada J, Tomoda S. Unusually short ethylene bond and large amplitude torsional motion of (E)-stilbenes in crystals. X-ray crystallographic study of 'stiff' stilbenes. Acta Cryst B 1995, 51:240-248.
38. Choi CH, Kertesz M, Karpfen A. The effects of electron correlation on the degree of bond alternation and electronic structure of oligomers of polyacetylene. J Chem Phys 1997, 107:6712-6721.
39. Van der Veen MH, Rispens MT, Jonkman HT, Hummelen JC. Molecules with linear π-conjugated pathways between all substituents: omniconjugation. Adv Funct Mater 2004, 14:215-223.
40. Gholami M, Tykwinski RR. Oligomeric and polymeric systems with a cross-conjugated π-framework. Chem Rev 2006, 106:4997-5027.
41. Milián-Medina B, Van Vooren A, Brocorens P, Gierschner J, Shkunov M, Heeney M, McCulloch I, Lazzaroni R, Cornil J. Electronic structure and charge-transport properties of polythiophene chains containing thienothiophene units: a joint experimental and theoretical study. Chem Mater 2007, 19:4949-4956.
42. Hennebicq E, Deleener C, Brédas JL, Scholes GD, Beljonne D. Chromophores in phenylenevinylene-based conjugated polymers: role of conformational kinks and chemical defects. J Chem Phys 2006, 125:054901-054916.
43. Gierschner J, Egelhaaf HJ, Mack HG, Schweizer S, Doser B, Oelkrug D. Optical spectra of oligothiophenes: vibronic states, torsional motions, and solvent ahifts. Synth Met 2003, 138:311-315.
44. Dutta T, Woody KB, Parkin SR, Watson MD, Gierschner J. Conjugated polymers with large effective stokes shift: benzobisdioxole-based poly(phenyleneethynylene)s. J Am Chem Soc 2009, 131:17321-17327.
45. Meier H. Conjugated oligomers with terminal donor-acceptor substitution. Angew Chem Int Ed 2005, 44:2482-2506.
46. Birks JB. Organic Molecular Photophysics. London, UK, John Wiley & Sons; 1973.
47. Kuhn H. Neuere untersuchungen über das elektronengasmodell organischer farbstoffe. Angew Chem 1958, 71:93-101.
48. Bruschi M, Limacher PA, Hutter J, Luthi HP. A scheme for the evaluation of electron delocalization and conjugation efficiency in linearly pi-conjugated systems. J Chem Theory Comput 2009, 5:506-514.
49. Tolbert LM, Zhao X. Beyond the cyanine limit: Peierls distortion and symmetry collapse in a polymethine dye. J Am Chem Soc 1997, 119:3253-3258.
50. Natan A, Zidon Y, Shapira Y, Kronik L. Cooperative effects and dipole formation at semiconductor and self-assembled-monolayer interfaces. Phys Rev B 2006, 73:193310.
51. Coropceanu V, Cornil J, da Silva Filho DA, Olivier Y, Silbey R, Brédas JL. Charge transport in organic semiconductors. Chem Rev 2007, 107:926-952.
52. Kasha M. Energy transfer mechanism and the molecular exciton model for molecular aggregates. Radiat Res 1963, 20:55-71.
53. Gierschner J, Huang Y-S, Van Averbeke B, Cornil J, Friend RH, Beljonne D. Excitonic versus electronic couplings in molecular assemblies: the importance of non-nearest neighbour interactions. J Chem Phys 2009, 130:044105/1-044105/6.
54. Spano F. The spectral signatures of Frenkel Polarons in H- and J-aggregates. Acc Chem Res 2010, 43:429-439.
55. Gierschner J, Ehni M, Egelhaaf HJ, Milián Medina B, Beljonne D, Benmansour H, Bazan GC. Solid state optical properties of linear polyconjugated molecules: π-stack contra herringbone. J Chem Phys 2005, 123:144914/1-144914/9.
56. Grimme S. Density functional theory with London dispersion corrections. WIREs Comput Mol Sci 2011, 1:211-228.