Skip to main content
SpringerLink
Log in

Describing excited states of [n]cycloparaphenylenes by hybrid and double-hybrid density functionals: from isolated to weakly interacting molecules

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

Abstract

We theoretically study the excited-state properties of cycloparaphenylenes ([n]CPPs) for a deeper understanding of their photochemical properties with increasing size n, being \(n = 6-12\) the number of repeat units forming the nanoring. We apply hybrid (e.g., PBE0 and PBE0-1/3), double-hybrid (e.g., PBE0-DH and PBE-QIDH) and range-separated (e.g., \(\omega\)B97X) functionals within a Time-Dependent (Tamm–Dancoff) Density Functional Theory framework. For the [6]CPP case, we concomitantly address changes in the set of selected excited states when going from an isolated molecule to a pair of self-assembled molecules, employing for that a dimer of parallel-like or tubular-like molecules according to the solid-state supramolecular organization found in real samples. These nanorings challenge standard theoretical methods due to the compromise needed between medium-range intramolecular (in isolated molecules) and long-range intermolecular (for weakly interacting pairs of molecules in condensed phases) interactions.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Golder MR, Jasti R (2015) Acc. Chem. Res. 48:557

    Article  CAS  Google Scholar 

  2. Lewis SE (2015) Chem Soc Rev 44:2221

    Article  CAS  Google Scholar 

  3. Jasti R, Bhattacharjee J, Neaton JN, Bertozzi CR (2008) J Am Chem Soc 130:17646

    Article  CAS  Google Scholar 

  4. Jasti R, Bertozzi CR (2010) Chem Phys Lett 494:1

    Article  CAS  Google Scholar 

  5. Yamago S, Watanabe Y, Iwamoto T (2011) Angew Chem Int Ed 50:3244

    Article  Google Scholar 

  6. Segawa Y, Omachi H, Itami K (2010) Org Lett 12:2262

    Article  CAS  Google Scholar 

  7. Bachrach S, Stück D (2010) J Org Chem 75:6595

    Article  CAS  Google Scholar 

  8. Iwamoto T, Watanabe Y, Sakamoto Y, Suzuki T, Yamago S (2011) J Am Chem Soc 133:8354

    Article  CAS  Google Scholar 

  9. Sisto TJ, Golder MR, Hirst ES, Jasti R (2011) J Am Chem Soc 133:15800

    Article  CAS  Google Scholar 

  10. Hitosugi S, Nakanishi W, Yamasaki T, Isobe H (2011) Nat Commun 2:492

    Article  Google Scholar 

  11. Li HB, Page AJ, Irle S, Morokuma K (2012) Chem Phys Chem 13:1479

    CAS  Google Scholar 

  12. Sisto TJ, Xian X, Jasti R (2012) J Org Chem 77:5857

    Article  CAS  Google Scholar 

  13. Darzi ER, Sisto TJ, Jasti R (2012) J Org Chem 77:6624

    Article  CAS  Google Scholar 

  14. Itami K (2012) Pure Appl Chem 84:907

    Article  CAS  Google Scholar 

  15. Xia J, Jasti R (2012) Angew Chem Int Ed 51:2474

    Article  CAS  Google Scholar 

  16. Kayahara E, Iwamoto T, Suzuki T, Yamago S (2013) Chem Lett 42:621

    Article  CAS  Google Scholar 

  17. Omachi H, Nakayama T, Takahashi E, Segawa Y, Itami K (2013) Nat Chem 5:572

    Article  CAS  Google Scholar 

  18. Fujitsuka M, Tojo S, Iwamoto T, Kayahara E, Yamago S, Majima T (2014) J Phys Chem Lett 5:2302

    Article  CAS  Google Scholar 

  19. Kayahara E, Patel VK, Yamago S (2014) J Am Chem Soc 136:2284

    Article  CAS  Google Scholar 

  20. Yamago S, Kayahara E, Iwamoto T (2014) Chem Rec 14:84

    Article  CAS  Google Scholar 

  21. Evans PE, Jasti R (2014) Top Curr Chem 349:249

    Article  CAS  Google Scholar 

  22. Evans PE, Darzi ER, Jasti R (2014) Nat Chem 6:404

    Article  CAS  Google Scholar 

  23. Alvarez MP, Burrezo PM, Kertesz M, Yamago S, Xia J, Jasti R, López Navarrete JT, Taravillo M, Baonza VG, Casado J (2014) Angew Chem Int Ed 53:7033

  24. Toriumi N, Muranaka A, Kayahara E, Yamago S, Uchiyama M (2015) J Am Chem Soc 137:82

    Article  CAS  Google Scholar 

  25. Hirst ES, Jasti R (2012) J Org Chem 77:10473

    Article  CAS  Google Scholar 

  26. Xia J, Bacon JW, Jasti R (2012) Chem Sci 3:3018

    Article  CAS  Google Scholar 

  27. Iwamoto T, Watanabe Y, Sadahiro T, Haino T, Yamago S (2011) Angew Chem Int Ed 50:8342

    Article  CAS  Google Scholar 

  28. Iwamoto T, Watanabe Y, Takaya H, Haino T, Yasuda N, Yamago S (2013) Chem Eur J 19:14061

    Article  CAS  Google Scholar 

  29. Iwamoto T, Slanina Z, Mizorogi N, Guo J, Akasaka T, Nagase S, Takaya H, Yasuda N, Kato T, Yamago S (2014) Chem Eur J 20:14403

    Article  CAS  Google Scholar 

  30. Rehman HU, McKee NA, McKee ML (2015) J. Comput. Chem. doi:10.1002/jcc.23979

  31. Xia J, Golder MR, Foster ME, Wong BM, Jasti R (2012) J Am Chem Soc 134:19709

    Article  CAS  Google Scholar 

  32. Wong BM (2009) J Phys Chem C 113:21921

    Article  CAS  Google Scholar 

  33. Wong BM, Lee JW (2011) J Phys Chem Lett 2:2702

    Article  CAS  Google Scholar 

  34. Segawa Y, Fukuzawa A, Matsuura S, Omachi H, Yamaguchi S, Irle S, Itami K (2012) Org Biomol Chem 10:5979

    Article  CAS  Google Scholar 

  35. Camacho C, Niehaus TA, Itami K, Irle S (2013) Chem Sci 4:187

    Article  CAS  Google Scholar 

  36. Adamska L, Nayyar I, Chen H, Swan AK, Oldani N, Fernández-Alberti N, Golder MR, Jasti R, Doorn SK, Tretiak S (2014) Nano Lett 14:6539

    Article  CAS  Google Scholar 

  37. Hines DA, Darzi ER, Jasti R, Kamat PV (2014) J Phys Chem A 118:1595

    Article  CAS  Google Scholar 

  38. Reddy VS, Camacho C, Xia J, Jasti R, Irle S (2014) J Chem Theory Comput 10:4025

    Article  CAS  Google Scholar 

  39. Liu J, Adamska L, Doorn SK, Tretiak S (2015) Phys Chem Chem Phys 17:14613

    Article  CAS  Google Scholar 

  40. Köhler A, Bässler H (2015) Electronic processes in organic semiconductors. Wiley-VCH, Weinheim

    Book  Google Scholar 

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

    Article  Google Scholar 

  42. Perdew JP, Ernzenhof M, Burke K (1996) J Chem Phys 105:9982

    Article  CAS  Google Scholar 

  43. Cortona P (2012) J Chem Phys 136:086101

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  48. Grimme S (1996) Chem Phys Lett 259:128

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. Moral M, Muccioli L, Son WJ, Olivier Y, Sancho-García JC (2015) J Chem Theory Comput 11:168

    Article  CAS  Google Scholar 

  51. Chantzis A, Laurent AD, Adamo C, Jacquemin D (2013) J Chem Theory Comput 9:4517

    Article  CAS  Google Scholar 

  52. Adamo C, Barone V (1999) J Chem Phys 110:6158

    Article  CAS  Google Scholar 

  53. Guido C, Brémond E, Adamo C, Cortona P (2013) J Chem Phys 138:021104

    Article  Google Scholar 

  54. Moore B, Charaf-Eddim A, Planchat A, Adamo C, Autschbach J, Jacquemin D (2014) J Chem Theory Comput 10:4599

    Article  CAS  Google Scholar 

  55. Jacquemin D, Adamo C (2015) Top Curr Chem 368:347

    Article  Google Scholar 

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

    Article  Google Scholar 

  57. Head-Gordon H, Rico RJ, Oumi M, Lee TJ (1994) Chem Phys Lett 219:21

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  59. Goerigk L, Grimme S (2010) J Chem Phys 132:184103

    Article  Google Scholar 

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

    Article  Google Scholar 

  61. Weigend F, Ahlrichs R (2005) Phys Chem Chem Phys 7:3297

    Article  CAS  Google Scholar 

  62. Klamt A, Schürmann G (1993) J Chem Soc Perkin Trans 2:799

    Article  Google Scholar 

  63. Andzelm J, Kömel C, Klamt A (1995) J Chem Phys 103:9312

    Article  CAS  Google Scholar 

  64. Sinnecker S, Rajendran A, Klamt A, Diedenhofen M, Neese F (2006) J Phys Chem A 110:2235

    Article  CAS  Google Scholar 

  65. Climent-Medina JV, Pérez-Jiménez AJ, Moral M, San-Fabián E, Sancho-García JC (2015) Chem Phys Chem 16:1520

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  67. Neese F (2003) J Comp Chem 24:1740

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  69. Fujitsuka M, Cho DW, Iwamoto T, Yamago S, Majima T (2012) Phys Chem Chem Phys 14:14585

    Article  CAS  Google Scholar 

  70. Chai JD, Head-Gordon M (2008) J Chem Phys 128:084106

    Article  Google Scholar 

  71. Chai JD, Head-Gordon M (2008) Phys Chem Chem Phys 10:6615

    Article  CAS  Google Scholar 

  72. Iikura H, Tsuneda T, Yanai T, Hirao K (2001) J Chem Phys 115:3540

    Article  CAS  Google Scholar 

  73. Caricato M, Trucks GW, Frisch MJ, Wiber KB (2011) J Chem Theory Comput 7:456

    Article  CAS  Google Scholar 

  74. Martin RL (2003) J Chem Phys 118:4775

    Article  CAS  Google Scholar 

  75. Plasser F, Thomitzni B, Bäppler SA, Wenzel J, Rehn DR, Wormit M, Dreuw A (2015) J Comput Chem 36:1609

    Article  CAS  Google Scholar 

  76. Guido CA, Cortona P, Mennucci B, Adamo C (2013) J Chem Theory Comput 9:3118

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  78. Le Bahers T, Adamo C, Ciofini I (2011) J Chem Theory Comput 7:2498

    Article  Google Scholar 

  79. Ciofini I, Le Bahers T, Adamo C, Odobel F, Jacquemin D (2012) J Phys Chem C 116:11946

    Article  CAS  Google Scholar 

  80. Etienne T, Assfeld X, Monari A (2014) J Chem Theory Comput 10:3896

    Article  CAS  Google Scholar 

  81. Etienne T, Assfeld X, Monari A (2014) J Chem Theory Comput 10:3906

    Article  CAS  Google Scholar 

  82. Moore B, Sun H, Govind N, Kowalski K, Autschbach J (2015) J Chem Theory Comput 11:3305

    Article  CAS  Google Scholar 

  83. Guido CA, Cortona P, Adamo C (2014) J Chem Phys 140:104101

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  86. Kasha M (1959) Rev Mod Phys 31:162

    Article  CAS  Google Scholar 

  87. Dreuw A, Head-Gordon M (2004) J Am Chem Soc 126:4007

    Article  CAS  Google Scholar 

  88. Barford W (2005) Electronic and optical properties of conjugated polymers. Oxford University Press, New York

    Google Scholar 

  89. Gierchner J, Park SY (2013) J Mater Chem C 1:5818

    Article  Google Scholar 

  90. Gierchner J, Lüer L, Milián-Medina B, Oelkrug D, Egelhaaf HJ (2013) J Phys Chem Lett 4:2686

    Article  Google Scholar 

  91. Gierchner J, Ehni M, Egelhaaf HJ, Milián-Medina B, Beljonne D, Benmansour H, Bazán GC (2005) J Chem Phys 123:144914

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the “Ministerio de Economía y Competitividad” of Spain and the “European Regional Development Fund” through Project CTQ2014-55073-P.

Author information

Authors and Affiliations

  1. Departamento de Química Física, Universidad de Alicante, 03080, Alicante, Spain

    J. C. Sancho-García & A. J. Pérez-Jiménez

  2. Institut de Recherche de Chimie Paris, IRCP CNRS UMR-8247, Chimie ParisTech, École Nationale Superieure de Chimie de Paris, 11 rue P. et M. Curie, 75231, Paris Cedex 05, France

    C. Adamo

  3. Institut Universitaire de France, 103 Boulevard Saint Michel, 75005, Paris, France

    C. Adamo

  4. CompuNet, Istituto Italiano di Tecnologia, 16163, Genoa, Italy

    C. Adamo

Authors
  1. J. C. Sancho-García
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. C. Adamo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. J. Pérez-Jiménez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to J. C. Sancho-García.

Additional information

Paper dedicated to the UNESCO International Year of Light and Light-based Technologies (IYL 2015).

Published as part of the special collection of articles “Health and Energy from the Sun”.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sancho-García, J.C., Adamo, C. & Pérez-Jiménez, A.J. Describing excited states of [n]cycloparaphenylenes by hybrid and double-hybrid density functionals: from isolated to weakly interacting molecules. Theor Chem Acc 135, 25 (2016). https://doi.org/10.1007/s00214-015-1778-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00214-015-1778-4

Keywords

Search

Navigation