Skip to main content
SpringerLink
Log in

On the performance of time-dependent double-hybrid density functionals for description of absorption and emission spectra of heteroaromatic compounds

  • Regular Article
  • Published:
Theoretical Chemistry Accounts Aims and scope Submit manuscript

Abstract

Theoretical chemistry provides a panel of powerful tools to investigate the geometries and electronic properties of excited states. However, it is necessary to benchmark the accuracy of existing models to determine the range of their applicability and accountability. In the present work, the performance of two related methodologies in this context, symmetry-adapted cluster-configuration interaction (SAC-CI) and time-dependent double-hybrid density functional theory (TD-DHDFT), is compared in detail for the calculation of absorption and fluorescence energies of small organic molecules and π-conjugated heteroaromatic compounds. Pragmatically, for the SAC-CI calculations the singles and doubles linked excitation operators are considered in the wave functions. On the other hand, for the TD-DHDFT calculations the linear-response Tamm–Dancoff formalism has been imposed. The considered DH density functionals include the approximations from both families of adjusted and non-adjusted models. Our numerical data reveal that of the tested adjusted DHs, B2-PLYP performs the best, while among the category of non-adjusted approximations the PBE0-DH functional outperforms others. Furthermore, the DH density functionals show deviations less than those obtained from SAC-CI method. Putting all the results together, the B2-PLYP and B2GP-PLYP functionals are found to be superior for overall performance. Altogether, the present contribution and recent efforts in this arena point out that besides the ground-state properties the DH approximations have also unquestionably entered into the field of excited-state calculations, where the DHDFT again comes into play and further evidence on the quality of the corresponding models is pronounced.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Nakatsuji H, Hirao K (1978) J Chem Phys 68:2053–2065

    Article  CAS  Google Scholar 

  2. Nakatsuji H (1978) Chem Phys Lett 59:362–364

    Article  CAS  Google Scholar 

  3. Nakatsuji H (1979) Chem Phys Lett 67:329–333

    Article  CAS  Google Scholar 

  4. Nakatsuji H (1997) Computational chemistry, reviews of current trends. In: Leszczynski J (ed) World Scientific, Singapore

  5. Mukherjee D, Mukherjee PK (1979) Chem Phys 39:325

    Article  CAS  Google Scholar 

  6. Geertsen J, Rittby M, Bartlett RJ (1989) Chem Phys Lett 164:57

    Article  CAS  Google Scholar 

  7. Andersson K, Malmqvist P-A, Roos BO, Sadlej AJ, Wolinski K (1990) J Phys Chem 94:5483

    Article  CAS  Google Scholar 

  8. Peyerimhoff SD, Buenker RJ (1975) Adv Quantum Chem 9:69

    Article  CAS  Google Scholar 

  9. Buenker RJ, Peyerimhoff SD (1968) Theor Chim Acta 12:183

    Article  CAS  Google Scholar 

  10. Hirao K (1992) Chem Phys Lett 190:374

    Article  CAS  Google Scholar 

  11. Runge E, Gross EKU (1984) Phys Rev Lett 52:997

    Article  CAS  Google Scholar 

  12. Casida ME (1995) Recent advances in density functional methods. Part I. In: Chong DP (ed) World Scientific, Singapore

  13. Dreuw A, Head-Gordon M (2005) Chem Rev 105:4009

    Article  CAS  Google Scholar 

  14. Jacquemin D, Perpète EA, Vydrov OA, Scuseria GE, Adamo C (2007) J Chem Phys 127:094102

    Article  CAS  Google Scholar 

  15. Ciofini I, Adamo C (2007) J Phys Chem A 111:5549

    Article  CAS  Google Scholar 

  16. Jacquemin D, Perpète EA, Scuseria GE, Ciofini I, Adamo C (2008) J Chem Theory Comput 4:123

    Article  CAS  Google Scholar 

  17. Schreiber M, Silva-Junior MR, Sauer SPA, Thiel W (2008) J Chem Phys 128:134110

    Article  CAS  Google Scholar 

  18. Silva-Junior MR, Schreiber M, Sauer SPA, Thiel W (2008) J Chem Phys 129:104103

    Article  CAS  Google Scholar 

  19. Peach MJG, Benfield P, Helgaker T, Tozer DJ (2008) J Chem Phys 128:044118

    Article  CAS  Google Scholar 

  20. Sauer SPA, Schreiber M, Silva-Junior MR, Thiel W (2009) J Chem Theory Comput 5:555

    Article  CAS  Google Scholar 

  21. Jacquemin D, Wathelet V, Perpète EA, Adamo C (2009) J Chem Theory Comput 5:2420

    Article  CAS  Google Scholar 

  22. Jacquemin D, Perpète EA, Ciofini I, Adamo C, Valero R, Zhao Y, Truhlar DG (2010) J Chem Theory Comput 6:2071

    Article  CAS  Google Scholar 

  23. Caricato M, Trucks GW, Frisch MJ, Wiberg KB (2010) J Chem Theory Comput 6:370

    Article  CAS  Google Scholar 

  24. Silva-Junior MR, Schreiber M, Sauer SPA, Thiel W (2010) J Chem Phys 133:174318

    Article  CAS  Google Scholar 

  25. Jacquemin D, Perpète EA, Ciofini I, Adamo C (2011) Theor Chem Acc 128:127

    Article  CAS  Google Scholar 

  26. Leang SS, Zahariev F, Gordon MS (2012) J Chem Phys 136:104101

    Article  CAS  Google Scholar 

  27. Mohajeri A, Alipour M (2012) Theor Chem Acc 131:1148

    Article  CAS  Google Scholar 

  28. Isegawa M, Peverati R, Truhlar DG (2012) J Chem Phys 137:244104

    Article  CAS  Google Scholar 

  29. Isegawa M, Truhlar DG (2013) J Chem Phys 138:134111

    Article  CAS  Google Scholar 

  30. Bousquet D, Fukuda R, Maitarad P, Jacquemin D, Ciofini I, Adamo C, Ehara M (2013) J Chem Theory Comput 9:2368

    Article  CAS  Google Scholar 

  31. Adamo C, Jacquemin D (2013) Chem Soc Rev 42:845

    Article  CAS  Google Scholar 

  32. Laurent AD, Jacquemin D (2013) Int J Quantum Chem 113:2019

    Article  CAS  Google Scholar 

  33. Alipour M (2014) J Phys Chem A 118:1741

    Article  CAS  Google Scholar 

  34. Escudero D, Thiel W (2014) J Chem Phys 140:194105

    Article  CAS  Google Scholar 

  35. Barnes L, Abdul-Al S, Allouche A (2014) J Phys Chem A 118:11033

    Article  CAS  Google Scholar 

  36. Fang C, Oruganti B, Durbeej B (2014) J Phys Chem A 118:4157

    Article  CAS  Google Scholar 

  37. Alipour M (2015) Theor Chem Acc 134:70

    Article  CAS  Google Scholar 

  38. Latouche C, Skouteris D, Palazzetti F, Barone V (2015) J Chem Theory Comput 11:3281

    Article  CAS  Google Scholar 

  39. Jacquemin D, Duchemin I, Blase X (2015) J Chem Theory Comput 11:5340

    Article  CAS  Google Scholar 

  40. Adamo C, Le Bahers T, Savarese M, Wilbraham L, Garcia G, Fukuda R, Ehara M, Rega N, Ciofini I (2015) Coord Chem Rev 304–305:166

    Article  CAS  Google Scholar 

  41. Ernzerhof M (1996) Chem Phys Lett 263:499

    Article  CAS  Google Scholar 

  42. Zhao Y, Lynch BJ, Truhlar DG (2004) J Phys Chem A 108:4786

    Article  CAS  Google Scholar 

  43. Zhao Y, Lynch BJ, Truhlar DG (2005) Phys Chem Chem Phys 7:43

    Article  CAS  Google Scholar 

  44. Grimme S (2006) J Chem Phys 124:034108

    Article  CAS  Google Scholar 

  45. Schwabe T, Grimme S (2006) Phys Chem Chem Phys 8:4398

    Article  CAS  Google Scholar 

  46. Tarnopolsky A, Karton A, Sertchook R, Vuzman D, Martin JML (2008) J Phys Chem A 112:3

    Article  CAS  Google Scholar 

  47. Karton A, Tarnopolsky A, Lamère J-F, Schatz GC, Martin JML (2008) J Phys Chem A 112:12868

    Article  CAS  Google Scholar 

  48. Sancho-García JC, Pérez-Jiménez AJ (2009) J Chem Phys 131:084108

    Article  CAS  Google Scholar 

  49. Benighaus T, DiStasio RA, Lochan RC, Chai J-D, Head-Gordon M (2008) J Phys Chem A 112:2702

    Article  CAS  Google Scholar 

  50. Graham DC, Menon AS, Goerigk L, Grimme S, Radom L (2009) J Phys Chem A 113:9861

    Article  CAS  Google Scholar 

  51. Zhang Y, Xu X, Goddard WA III (2009) Proc Natl Acad Sci USA 106:4963

    Article  CAS  Google Scholar 

  52. Kozuch S, Gruzman D, Martin JML (2010) J Phys Chem C 114:20801

    Article  CAS  Google Scholar 

  53. Zhang Y, Xu X, Jung Y, Goddard WA III (2011) Proc Natl Acad Sci USA 108:19896

    Article  CAS  Google Scholar 

  54. Goerigk L, Grimme SJ (2011) Chem Theory Comput 7:291

    Article  CAS  Google Scholar 

  55. Sharkas K, Toulouse J, Savin A (2011) J Chem Phys 134:064113

    Article  CAS  Google Scholar 

  56. Brémond E, Adamo C (2011) J Chem Phys 135:024106

    Article  CAS  Google Scholar 

  57. Toulouse J, Sharkas K, Brémond E, Adamo C (2011) J Chem Phys 135:101102

    Article  CAS  Google Scholar 

  58. Fromager E (2011) J Chem Phys 135:244106

    Article  CAS  Google Scholar 

  59. Kozuch S, Martin JML (2011) Phys Chem Chem Phys 13:20104

    Article  CAS  Google Scholar 

  60. Zhang IY, Su NQ, Brémond E, Adamo C, Xu X (2012) J Chem Phys 136:174103

    Article  CAS  Google Scholar 

  61. Chai J-D, Mao S-P (2012) Chem Phys Lett 538:121

    Article  CAS  Google Scholar 

  62. Mohajeri A, Alipour M (2012) J Chem Phys 136:124111

    Article  CAS  Google Scholar 

  63. Peverati R, Head-Gordon M (2013) J Chem Phys 139:024110

    Article  CAS  Google Scholar 

  64. Zhang IY, Xu X (2013) J Phys Chem Lett 4:1669

    Article  CAS  Google Scholar 

  65. Bousquet D, Brémond E, Sancho-García JC, Ciofini I, Adamo C (2013) J Chem Theory Comput 9:3444

    Article  CAS  Google Scholar 

  66. Kozuch S, Martin JML (2013) J Comput Chem 34:2327

    CAS  Google Scholar 

  67. Su NQ, Adamo C, Xu X (2013) J Chem Phys 139:174106

    Article  CAS  Google Scholar 

  68. Cornaton Y, Franck O, Teale AM, Fromager E (2013) Mol Phys 111:1275

    Article  CAS  Google Scholar 

  69. Aragó J, Ortí E, Sancho-García JC (2013) J Chem Theory Comput 9:3437

    Article  CAS  Google Scholar 

  70. Alipour M (2013) J Phys Chem A 117:4506

    Article  CAS  Google Scholar 

  71. Su NQ, Yang W, Sánchez PM, Xu X (2014) J Phys Chem A 118:9201

    Article  CAS  Google Scholar 

  72. Su NQ, Xu X (2014) J Chem Phys 140:18A512

    Article  CAS  Google Scholar 

  73. Souvi SMO, Sharkas K, Toulouse J (2014) J Chem Phys 140:084107

    Article  CAS  Google Scholar 

  74. Thompson LM, Hratchian HP (2014) J Chem Phys 141:034108

    Article  CAS  Google Scholar 

  75. Sharkas K, Toulouse J, Maschio L, Civalleri B (2014) J Chem Phys 141:044105

    Article  CAS  Google Scholar 

  76. Cornaton Y, Fromager E (2014) Int J Quantum Chem 114:1199

    Article  CAS  Google Scholar 

  77. Alipour M (2014) J Phys Chem A 118:5333

    Article  CAS  Google Scholar 

  78. Yu F (2014) J Phys Chem A 118:3175

    Article  CAS  Google Scholar 

  79. Brémond E, Sancho-García JC, Pérez-Jiménez AJ, Adamo C (2014) J Chem Phys 141:031101

    Article  CAS  Google Scholar 

  80. Alipour M (2015) Theor Chem Acc 134:87

    Article  CAS  Google Scholar 

  81. Kim J, Jung Y (2015) J Chem Theory Comput 11:45

    Article  CAS  Google Scholar 

  82. Bousquet D, Brémond E, Sancho-García JC, Ciofini I, Adamo C (2015) Theor Chem Acc 134:1602

    Article  CAS  Google Scholar 

  83. Wykes M, Pérez-Jiménez AJ, Adamo C, Sancho-García JC (2015) J Chem Phys 142:224105

    Article  CAS  Google Scholar 

  84. Savarese M, Brémond E, Pérez-Jiménez AJ, Sancho-García JC, Adamo C (2015) J Phys Chem Lett 6:3540

    Article  CAS  Google Scholar 

  85. Zhang IY, Xu X (2011) Int Rev Phys Chem 30:115

    Article  CAS  Google Scholar 

  86. Sancho-García JC, Adamo C (2013) Phys Chem Chem Phys 15:14581

    Article  CAS  Google Scholar 

  87. Goerigk L, Grimme S (2014) WIREs Comput Mol Sci 4:576

    Article  CAS  Google Scholar 

  88. Su NQ, Xu X (2015) Int J Quantum Chem 115:589

    Article  CAS  Google Scholar 

  89. Harris J (1984) Phys Rev A 29:1648

    Article  CAS  Google Scholar 

  90. Grimme S, Neese F (2007) J Chem Phys 127:154116

    Article  CAS  Google Scholar 

  91. Goerigk L, Grimme SJ (2010) Chem Phys 132:184103

    Google Scholar 

  92. Goerigk L, Grimme S (2008) ChemPhysChem 9:2467

    Article  CAS  Google Scholar 

  93. Goerigk L, Grimme S (2009) J Phys Chem A 113:767

    Article  CAS  Google Scholar 

  94. Goerigk L, Moellmann J, Grimme S (2009) Phys Chem Chem Phys 11:4611

    Article  CAS  Google Scholar 

  95. Send R, Valsson O, Filippi C (2011) J Chem Theory Comput 7:444

    Article  CAS  Google Scholar 

  96. Goerigk L, Grimme S (2011) J Chem Theory Comput 7:3272

    Article  CAS  Google Scholar 

  97. Di Meo F, Trouillas P, Adamo C, Sancho-García JC (2013) J Chem Phys 139:164104

    Article  CAS  Google Scholar 

  98. Neese F (2012) WIREs Comput Mol Sci 2:73

    Article  CAS  Google Scholar 

  99. Hirata S, Head-Gordon M (1999) Chem Phys Lett 314:291

    Article  CAS  Google Scholar 

  100. Perdew JP, Burke K, Ernzerhof M (1996) Phys Rev Lett 77:3865

    Article  CAS  Google Scholar 

  101. Becke AD (1988) Phys Rev A 38:3098

    Article  CAS  Google Scholar 

  102. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  103. Neese F (2003) J Comput Chem 24:1740

    Article  CAS  Google Scholar 

  104. Neese F, Wennmohs F, Hansen A, Becker U (2009) Chem Phys 356:98

    Article  CAS  Google Scholar 

  105. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09 revision A.02. Gaussian Inc, Wallingford

  106. McDiarmid R, Sablijć A (1988) J Chem Phys 89:6086

    Article  CAS  Google Scholar 

  107. John WM III, Estler RC, Doering JP (1974) J Chem Phys 61:763

    Article  Google Scholar 

  108. Doering JP, McDiarmid R (1981) J Chem Phys 75:2477

    Article  CAS  Google Scholar 

  109. Flicker M, Mosher OA, Kupperman A (1978) Chem Phys 30:307

    Article  CAS  Google Scholar 

  110. McDiarmid R, Sabljić A (1991) J Phys Chem 95:6455

    Article  CAS  Google Scholar 

  111. Sabljić A, McDiarmid R, Gedanken A (1992) J Phys Chem 96:2442

    Article  Google Scholar 

  112. Price WC, Walsh AD (1941) Proc R Soc Lond Ser A 179:201

    Article  CAS  Google Scholar 

  113. Serrano-Andres L, Merchan M, Nebot-Gil I, Lindh R, Roos BO (1993) J Chem Phys 98:3151

    Article  CAS  Google Scholar 

  114. Robin MB (1985) Higher excited sates of polyatomic molecules. Academic, New York

    Google Scholar 

  115. Derrick PJ, Ǻsbrink L, Edqvist O, Jonsson B-Ö, Lindholm E (1971) Int J Mass Spectrom Ion Phys 6:161

    Article  CAS  Google Scholar 

  116. Flicker WM, Mosher OA, Kupperman A (1976) J Chem Phys 64:1315

    Article  CAS  Google Scholar 

  117. Trommsdorff HP (1972) J Chem Phys 56:5358

    Article  CAS  Google Scholar 

  118. Brint P, Connerade J-P, Tsekeris P, Bolovinos A, Baig A (1986) J Chem Soc, Faraday Trans II 82:367

    Article  CAS  Google Scholar 

  119. Goodman J, Brus LE (1978) J Chem Phys 69:1604

    Article  CAS  Google Scholar 

  120. Hackmeyer H, Whitten JL (1971) J Chem Phys 54:3739

    Article  CAS  Google Scholar 

  121. Wadt WR, Goddard WA, Dunning TH (1976) J Chem Phys 65:438

    Article  CAS  Google Scholar 

  122. Bolovinos A, Tsekeris P, Philis J, Pantons E, Andritsopoulos G (1984) J Mol Spectrosc 103:240

    Article  CAS  Google Scholar 

  123. Walker IC, Palmer MH, Hopkirk A (1989) Chem Phys 141:365

    Article  Google Scholar 

  124. Bavia M, Bertinelli F, Taliani C, Zauli C (1976) Mol Phys 31:479

    Article  CAS  Google Scholar 

  125. Wan J, Meller J, Hada M, Ehara M, Nakatsuji H (2000) J Chem Phys 113:7853

    Article  CAS  Google Scholar 

  126. Daniels M, Hanswirth W (1971) Science 171:675

    Article  CAS  Google Scholar 

  127. Wintgens V, Valat P, Kossanyi J, Biczok L, Demeter A, Berces T (1994) J Chem Soc. Faraday Trans II 90:411

    Article  CAS  Google Scholar 

  128. Itoh T (1995) Chem Rev 95:2351

    Article  CAS  Google Scholar 

  129. Jacquemin D, Perpète EA, Scalmani G, Frisch MJ, Assfeld X, Ciofini I, Adamo C (2006) J Chem Phys 125:164324

    Article  CAS  Google Scholar 

  130. Polewski K, Zinger D, Trunk J, Sutherland JC (2011) Radiat Phys Chem 80:1092

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The author acknowledges Shiraz University for providing computational resources.

Author information

Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Iran

    Mojtaba Alipour

Authors
  1. Mojtaba Alipour
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mojtaba Alipour.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alipour, M. On the performance of time-dependent double-hybrid density functionals for description of absorption and emission spectra of heteroaromatic compounds. Theor Chem Acc 135, 67 (2016). https://doi.org/10.1007/s00214-016-1838-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00214-016-1838-4

Keywords

Search

Navigation