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Theoretical Chemistry Accounts

, Volume 120, Issue 4–6, pp 405–410 | Cite as

On the TD-DFT UV/vis spectra accuracy: the azoalkanes

  • Denis JacqueminEmail author
  • Eric A. Perpète
  • Ilaria Ciofini
  • Carlo AdamoEmail author
Regular Article

Abstract

Using an ab intio TD-DFT approach systematically accounting for the molecular surroundings effects, we have computed the n → π* absorption wavelength of 22 azoalkane derivatives. For the complete set of molecules, we propose a theoretical procedure able to reproduce the major auxochromic effects, and to deliver a mean absolute error of 5.8 nm (0.056 eV) with maximal deviations limited to 21 nm (0.20 eV). The impact of including in the model explicit solvent molecules is discussed as well. This contribution confirms that PCM-TD-PBE0 is a first-grade method for simulating the vertical absorption spectra of organic dyes.

Keywords

Azoalkane Azo derivatives TD-DFT Absorption spectra n→ π* transitions 

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References

  1. 1.
    Runge E and Gross EKU (1984). Phys Rev Lett 52: 997 CrossRefGoogle Scholar
  2. 2.
    Burke K, Werschnik J and Gross EKU (2005). J Chem Phys 123: 062206 CrossRefGoogle Scholar
  3. 3.
    van Caillie C and Amos RD (1999). Chem Phys Lett 308: 249 CrossRefGoogle Scholar
  4. 4.
    van Caillie C and Amos RD (2000). Chem Phys Lett 317: 159 CrossRefGoogle Scholar
  5. 5.
    Furche F and Ahlrichs R (2002). J Chem Phys 117: 7433 CrossRefGoogle Scholar
  6. 6.
    Jacquemin D, Perpète EA, Scalmani G, Frisch MJ, Assfeld X, Ciofini I and Adamo C (2006). J Chem Phys 125: 164324 CrossRefGoogle Scholar
  7. 7.
    Cossi M and Barone V (2001). J Chem Phys 115: 4708 CrossRefGoogle Scholar
  8. 8.
    Tozer DJ (2003). J Chem Phys 119: 12697 CrossRefGoogle Scholar
  9. 9.
    Dreuw A and Head-Gordon M (2004). J Am Chem Soc 126: 4007 CrossRefGoogle Scholar
  10. 10.
    Ciofini I and Adamo C (2007). J Phys Chem A 111: 5549 CrossRefGoogle Scholar
  11. 11.
    Tawada T, Tsuneda T, Yanagisawa S, Yanai T and Hirao K (2004). J Chem Phys 120: 8425 CrossRefGoogle Scholar
  12. 12.
    Rudberg E, Salek P, Helgaker T and Agren H (2005). J Chem Phys 123: 184108 CrossRefGoogle Scholar
  13. 13.
    Chiba M, Tsuneda T and Hirao K (2006). J Chem Phys 124: 144106 CrossRefGoogle Scholar
  14. 14.
    Cai ZL, Crossley MJ, Reimers JR, Kobayashi R and Amos RD (2006). J Phys Chem B 110: 15624 CrossRefGoogle Scholar
  15. 15.
    Vydrov OA and Scuseria GE (2006). J Chem Phys 125: 234109 CrossRefGoogle Scholar
  16. 16.
    Peach MJG, Cohen AJ and Tozer DJ (2006). Phys Chem Chem Phys 8: 4543 CrossRefGoogle Scholar
  17. 17.
    Jacquemin D, Preat J and Perpète EA (2005). Chem Phys Lett 410: 254 CrossRefGoogle Scholar
  18. 18.
    Jacquemin D, Preat J, Wathelet V and Perpète EA (2006). J Chem Phys 124: 074104 CrossRefGoogle Scholar
  19. 19.
    Jacquemin D, Preat J, Wathelet V, Fontaine M and Perpète EA (2006). J Am Chem Soc 128: 2072 CrossRefGoogle Scholar
  20. 20.
    Guillaumont D and Nakamura S (2000). Dyes Pigm 46: 85 CrossRefGoogle Scholar
  21. 21.
    Fabian J (2001). Theor Chem Acc 106: 199 Google Scholar
  22. 22.
    Schreiber M, Bub V and Fülscher MP (2001). Phys Chem Chem Phys 3: 3906 CrossRefGoogle Scholar
  23. 23.
    Petit L, Adamo C and Russo N (2005). J Phys Chem B 109: 12214 CrossRefGoogle Scholar
  24. 24.
    Petit L, Quartarolo A, Adamo C and Russo N (2006). J Phys Chem B 110: 2398 CrossRefGoogle Scholar
  25. 25.
    Quartarolo AD, Russo N and Sicilia E (2006). Chem Eur J 12: 6797 CrossRefGoogle Scholar
  26. 26.
    Leopoldini M, Russo N, Chiodo S and Toscano M (2006). J Agr Food Chem 54: 6343 CrossRefGoogle Scholar
  27. 27.
    Quartarolo AD, Russo N, Sicilia E and Lelj F (2007). J Chem Theory Comput 3: 860 CrossRefGoogle Scholar
  28. 28.
    Griffiths J (1976). Colour and constitution of organic molecules. Academic Press, London Google Scholar
  29. 29.
    Fabian J, Diaz LA, Seifert G and Niehaus T (2002). J Mol Struct (THEOCHEM) 594: 41 CrossRefGoogle Scholar
  30. 30.
    Jacquemin D, Wathelet V and Perpète EA (2006). J Phys Chem A 110: 9145 CrossRefGoogle Scholar
  31. 31.
    Jacquemin D and Perpète EA (2006). Chem Phys Lett 420: 529 CrossRefGoogle Scholar
  32. 32.
    Fliegl H, Köhn A, Hättig C and Ahlrichs R (2003). J Am Chem Soc 125: 9821 CrossRefGoogle Scholar
  33. 33.
    Chen PC, Chieh YC and Wu JC (2005). J Mol Struct (THEOCHEM) 715: 183 CrossRefGoogle Scholar
  34. 34.
    Liu JN, Yuan SF and Chen ZR (2005). J Mol Struct (THEOCHEM) 730: 151 CrossRefGoogle Scholar
  35. 35.
    Briquet L, Vercauteren DP, Perpète EA and Jacquemin D (2006). Chem Phys Lett 417: 190 CrossRefGoogle Scholar
  36. 36.
    Briquet L, Vercauteren DP, André JM, Perpète EA and Jacquemin D (2007). Chem Phys Lett 435: 257 CrossRefGoogle Scholar
  37. 37.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C and Pople JA (2004). Gaussian 03, Revision C.02. Gaussian, Wallingford Google Scholar
  38. 38.
    Perpète EA, Wathelet V, Preat J, Lambert C and Jacquemin D (2006). J Chem Theory Comput 2: 434 CrossRefGoogle Scholar
  39. 39.
    Jacquemin D, Bouhy M and Perpète EA (2006). J Chem Phys 124: 204321 CrossRefGoogle Scholar
  40. 40.
    Becke AD (1993). J Chem Phys 98: 5648 CrossRefGoogle Scholar
  41. 41.
    Stephens PJ, Devlin FJ, Chabalowski CF and Frisch MJ (1994). J Phys Chem 98: 11623 CrossRefGoogle Scholar
  42. 42.
    Adamo C, Scuseria GE and Barone V (1999). J Chem Phys 111: 2889 CrossRefGoogle Scholar
  43. 43.
    Curtiss LA, Raghavachari K, Referm PC and Pople JA (1997). Chem Phys Lett 270: 419 CrossRefGoogle Scholar
  44. 44.
    Barone V and Adamo C (1996). J Chem Phys 105: 11007 CrossRefGoogle Scholar
  45. 45.
    Adamo C and Barone V (1999). J Chem Phys 110: 6158 CrossRefGoogle Scholar
  46. 46.
    Ernzerhof M and Scuseria GE (1999). J Chem Phys 110: 5029 CrossRefGoogle Scholar
  47. 47.
    Pezzella A, Panzella L, Crescenzi O, Napolitano A, Navaratman S, Edge R, Land E, Barone V and d’Ischia M (2006). J Am Chem Soc 128: 15490 CrossRefGoogle Scholar
  48. 48.
    Santoro F, Improta R, Lami A, Bloino J and Barone V (2007). J Chem Phys 126: 084509 CrossRefGoogle Scholar
  49. 49.
    Improta R, Barone V and Santoro F (2007). Angew Chem Int Ed Engl 46: 405 CrossRefGoogle Scholar
  50. 50.
    Jacquemin D, Perpète EA, Vydrov OA, Scuseria GE and Adamo C (2007). J Chem Phys 127: 094102 CrossRefGoogle Scholar
  51. 51.
    Tomasi J, Mennucci B and Cammi R (2005). Chem Rev 105: 2999 CrossRefGoogle Scholar
  52. 52.
    Mirbach MJ, Liu KC, Mirbach MF, Cherry WR, Turro NJ and Engel PS (1978). J Am Chem Soc 100: 5122 CrossRefGoogle Scholar
  53. 53.
    Jacquemin D, Perpète EA, Scuseria GE, Ciofini I, Adamo C (2008) J Chem Theory Comput 4:123Google Scholar
  54. 54.
    Nguyen KA, Kennel J and Pachter R (2002). J Chem Phys 117: 7128 CrossRefGoogle Scholar
  55. 55.
    Robertson LC and Merritt JA (1972). J Chem Phys 57: 941 CrossRefGoogle Scholar
  56. 56.
    Robertson LC and Merritt JA (1972). J Chem Phys 57: 2919 CrossRefGoogle Scholar
  57. 57.
    Engel PS, Hayes RA, Keifer L, Szilagyi S and Tomberlake JW (1978). J Am Chem Soc 100: 1876 CrossRefGoogle Scholar
  58. 58.
    Overberger CG, Anselme JP and Hall JR (1963). J Am Chem Soc 85: 2752 CrossRefGoogle Scholar
  59. 59.
    Solomon BS, Thomas TF and Steel C (1968). J Am Chem Soc 90: 2249 CrossRefGoogle Scholar
  60. 60.
    Cohen SG, Zand R and Steel C (1961). J Am Chem Soc 83: 2895 CrossRefGoogle Scholar
  61. 61.
    Cohen SG and Zand R (1962). J Am Chem Soc 84: 586 CrossRefGoogle Scholar
  62. 62.
    Hutton RF and Steel C (1964). J Am Chem Soc 86: 745 CrossRefGoogle Scholar
  63. 63.
    Robin MB and Simpson WT (1962). J Chem Phys 36: 580 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  1. 1.Laboratoire de Chimie Théorique Appliquée, Groupe de Chimie PhysiqueThéorique et Structurale, Facultés Universitaires Notre-Dame de la PaixNamurBelgium
  2. 2.Ecole Nationale Supérieure de Chimie de Paris, Laboratoire Electrochimie et Chimie AnalytiqueUMR CNRS-ENSCP no. 7575Paris Cedex 05France

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