Skip to main content

Advertisement

SpringerLink
Log in

Virtual eyes for technology and cultural heritage: towards computational strategy for new and old indigo-based dyes

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

Abstract

A cost-effective, robust and reliable computational strategy is applied to simulate peak positions and band shapes of UV–Vis spectra together with the dye colours perceived by human eyes. The features of our virtual multifrequency spectrometer (VMS) relevant to this topic are sketched with special focus on the selection of density functional, vibronic model and solvent description. Furthermore, the new VMS-draw graphical user interface is employed for user-friendly pre- and post-processing of the computed data. The family of indigo dyes is used as case study in view of their continued use in the field of cultural heritage, together with new promising applications for photonics and sustainable energy. After assessment of different simplified models employed in previous studies, the role of several substituents and of dimerization in tuning the colour and spectral features are analysed in detail by means of both accurate computations and interpretative models. The results are in remarkable agreement with experiment and allow to rationalize the behaviour of this class of dyes.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. Barone V (ed) (2011) Computational strategies for spectroscopy, from small molecules to nano systems. Wiley, Hoboken

    Google Scholar 

  2. Kobayashi H, Ogawa M, Alford R, Choyke PL, Urano Y (2010) Chem. Rev. 110:2620

    Article  CAS  Google Scholar 

  3. Kamerlin SCL, Warshel A (2011) Phys. Chem. Chem. Phys. 13:10401

    Article  CAS  Google Scholar 

  4. Pedone A, Prampolini G, Monti S, Barone V (2011) Chem. Mater. 23:5016

    Article  CAS  Google Scholar 

  5. Curutchet C, Kongsted J, Munoz-Losa A, Hossein-Nejad H, Scholes GD, Mennucci B (2011) J. Am. Chem. Soc. 133:3078

    Article  CAS  Google Scholar 

  6. König C, Neugebauer J (2012) Chem. Phys. Chem. 13:386

    Google Scholar 

  7. Labat F, Le Bahers T, Ciofini I, Adamo C (2012) Acc. Chem. Res. 45:1268

    Article  CAS  Google Scholar 

  8. Prampolini G, Bellina F, Biczysko M, Cappelli C, Carta L, Lessi M, Pucci A, Ruggeri G, Barone V (2013) Chem. Eur. J. 19:1996

    Article  CAS  Google Scholar 

  9. Ribeiro AJM, Alberto ME, Ramos MJ, Fernandes PA, Russo N (2013) Chem. Eur. J 19:14081

    Article  CAS  Google Scholar 

  10. Pedone A, Gambuzzi E, Barone V, Bonacchi S, Genovese D, Rampazzo E, Prodi L, Montalti M (2013) Phys. Chem. Chem. Phys. 15:12360

    Article  CAS  Google Scholar 

  11. Dreuw A, Faraji S (2013) Phys. Chem. Chem. Phys. 15:19957

    Article  CAS  Google Scholar 

  12. Boixel J, Guerchais V, Le Bozec H, Jacquemin D, Amar A, Boucekkine A, Colombo A, Dragonetti C, Marinotto D, Roberto D, Righetto S, De Angelis R (2014) J. Am. Chem. Soc. 136:5367

    Article  CAS  Google Scholar 

  13. Laurent AD, Adamo C, Jacquemin D (2014) Phys. Chem. Chem. Phys. 16:14334

    Article  CAS  Google Scholar 

  14. Goez A, Jacob CR, Neugebauer J (2014) Comput. Theor. Chem. 1040–1041:347

    Article  CAS  Google Scholar 

  15. Horch M, Hildebrandt P, Zebger I (2015) Phys. Chem. Chem. Phys. 17:18222

    Article  CAS  Google Scholar 

  16. Imahori H, Umeyama T, Ito S (2009) Acc. Chem. Res. 42:1809

    Article  CAS  Google Scholar 

  17. Debije MG, Verbunt PPC (2012) Adv. Energy Mater. 2:12

    Article  CAS  Google Scholar 

  18. WGvan Sark (2013) Renew. Energy 49:207

    Article  CAS  Google Scholar 

  19. Reimers JR, Cai ZL, Kobayashi R, Ratsep M, Freiberg A, Krausz E (2013) Sci. Rep. 3:2761

    Article  Google Scholar 

  20. Renger T, Muh F (2013) Phys. Chem. Chem. Phys. 15:3348

    Article  CAS  Google Scholar 

  21. Miliani C, Romani A, Favaro G (1998) Spectrochim. Acta A 54:581

    Article  Google Scholar 

  22. Pouli P, Selimis A, Georgiou S, Fotakis C (2010) Acc. Chem. Res. 43:771

    Article  CAS  Google Scholar 

  23. Fantacci S, Amat A, Sgamellotti A (2010) Acc. Chem. Res. 43:802

    Article  CAS  Google Scholar 

  24. Rosi F, Miliani C, Clementi C, Kahrim K, Presciutti F, Vagnini M, Manuali V, Daveri A, Cartechini L, Brunetti BG, Sgamellotti A (2010) Appl. Phys. A 100:613

    Article  CAS  Google Scholar 

  25. Amat A, Rosi F, Miliani C, Sgamellotti A, Fantacci S (2011) J. Mol. Struct. 993:43

    Article  CAS  Google Scholar 

  26. Carta L, Biczysko M, Bloino J, Licari D, Barone V (2014) Phys. Chem. Chem. Phys. 16:2897

    Article  CAS  Google Scholar 

  27. Grunenberg J (ed) (2010) Computational spectroscopy: methods, experiments and applications. Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim

    Google Scholar 

  28. Quack M, Merkt F (eds) (2011) Handbook of high-resolution spectroscopy. Wiley, New York

    Google Scholar 

  29. Barone V (2014) Reference module in chemistry, molecular sciences and chemical engineering. Elsevier, New York. doi:10.1016/B978-0-12-409547-2.05400-7

  30. Burke K, Werschnik J, Gross EKU (2005) J. Chem. Phys. 123:062206

    Article  CAS  Google Scholar 

  31. Casida ME (2009) J. Mol. Struct. Theochem. 914:3

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  35. Furche F, Ahlrichs R (2004) J. Chem. Phys. 121:12772

    Article  CAS  Google Scholar 

  36. Scalmani G, Frisch MJ, Mennucci B, Tomasi J, Cammi R, Barone V (2006) J. Chem. Phys. 124:094107

    Article  CAS  Google Scholar 

  37. Liu J, Liang W (2011) J. Chem. Phys. 135:184111

    Article  CAS  Google Scholar 

  38. Liu J, Liang W (2013) J. Chem. Phys. 138:024101

    Article  CAS  Google Scholar 

  39. Barone V, Baiardi A, Biczysko M, Bloino J, Cappelli C, Lipparini F (2012) Phys. Chem. Chem. Phys. 14:12404

    Article  CAS  Google Scholar 

  40. Biczysko M, Bloino J, Brancato G, Cacelli I, Cappelli C, Ferretti A, Lami A, Monti S, Pedone A, Prampolini G, Puzzarini C, Santoro F, Trani F, Villani G (2012) Theor. Chem. Acc. 131:1201/1

    Article  CAS  Google Scholar 

  41. Barone V, Biczysko M, Bloino J, Carta L, Pedone A (2014) Comput. Theor. Chem. 1037:35

    Article  CAS  Google Scholar 

  42. Vazart F, Latouche C, Bloino J, Barone V (2015) Inorg. Chem. 54:5588

    Article  CAS  Google Scholar 

  43. Latouche C, Baiardi A, Barone V (2015) J. Phys. Chem. B 119:7253

    Article  CAS  Google Scholar 

  44. Chenu A, Christensson N, Kauffmann HF, Mancal T (2012) Sci. Rep. 3:2029

    Google Scholar 

  45. Kolli A, O’Reilly EJ, Scholes GD, Olaya-Castro A (2012) J. Chem. Phys. 137:174109

    Article  CAS  Google Scholar 

  46. Barone V, Biczysko M, Borkowska-Panek M, Bloino J (2014) ChemPhysChem 15:3355

    Article  CAS  Google Scholar 

  47. Etinski M, Petković M, Ristić MM, Marian CM (2015) J. Phys. Chem. B 119:10156

    Article  CAS  Google Scholar 

  48. Jacquemin D, Bremond E, Ciofini I, Adamo C (2012) J. Phys. Chem. Lett. 3:468

    Article  CAS  Google Scholar 

  49. Santoro F, Improta R, Lami A, Bloino J, Barone V (2007) J. Chem. Phys. 126:084509

    Article  CAS  Google Scholar 

  50. Barone V, Bloino J, Biczysko M, Santoro F (2009) J. Chem. Theory Comput. 5:540

    Article  CAS  Google Scholar 

  51. Bloino J, Biczysko M, Santoro F, Barone V (2010) J. Chem. Theory Comput. 6:1256

    Article  CAS  Google Scholar 

  52. Baiardi A, Bloino J, Barone V (2013) J. Chem. Theory Comput. 9:4097

    Article  CAS  Google Scholar 

  53. Petrenko T, Neese F (2007) J. Chem. Phys. 127:164319

    Article  CAS  Google Scholar 

  54. Petrenko T, Neese F (2012) J. Chem. Phys. 137:234107

    Article  CAS  Google Scholar 

  55. Dierksen M, Grimme S (2004) J. Chem. Phys. 120:3544

    Article  CAS  Google Scholar 

  56. Jankowiak HC, Stuber JL, Berger R (2007) J. Chem. Phys. 127:234101

    Article  CAS  Google Scholar 

  57. Dierksen M, Grimme S (2005) J. Chem. Phys. 122:244101

    Article  CAS  Google Scholar 

  58. Barone V, Baiardi A, Bloino J (2014) Chirality 26:588

    Article  CAS  Google Scholar 

  59. Bloino J, Biczysko M, Barone V (2012) J. Chem. Theory Comput. 8:1015

    Article  CAS  Google Scholar 

  60. Bloino J, Barone V (2012) J. Chem. Phys. 136:124108

    Article  CAS  Google Scholar 

  61. Bloino J (2015) J. Phys. Chem. A 119:5269

    Article  CAS  Google Scholar 

  62. Baiardi A, Bloino J, Barone V (2014) J. Chem. Phys. 141:114108

    Article  CAS  Google Scholar 

  63. Licari D, Baiardi A, Biczysko M, Egidi F, Latouche C, Barone V (2015) J. Comput. Chem. 36:321

    Article  CAS  Google Scholar 

  64. Biczysko M, Bloino J, Santoro F, Barone V (2011) In: Barone V (ed) Computational strategies for spectroscopy, from small molecules to nano systems. Wiley, Chichester, pp 361–443

    Chapter  Google Scholar 

  65. Lami A, Santoro F (2011) In: Barone V (ed) Computational strategies for spectroscopy, from small molecules to nano systems. Wiley, Chichester, pp 475–516

    Chapter  Google Scholar 

  66. Clark RJ, Cooksey CJ, Daniels MA, Withnall R (1993) Endeavour 17:191

    Article  CAS  Google Scholar 

  67. Zollinger H (2003) Color chemistry. Syntheses, properties and application of organic dyes and pigments, 3rd revised edn. Wiley-VCH, Weinheim

  68. Hunger K (ed) (2004) Industrial dyes. Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim

    Google Scholar 

  69. Baeyer A, Drewsen V (1882) Ber. Deutsch. Chem. Ges. 15:2856

    Article  Google Scholar 

  70. Giustetto R, Xamena Llabrési FX, Ricchiardi G, Bordiga S, Damin A, Gobetto R, Chierotti MR (2005) J. Phys. Chem. B 109:19360

    Article  CAS  Google Scholar 

  71. Lüttke W, Hermann H, Klessinger M (1966) Angew. Chem. Int. Ed. 5:598

    Article  Google Scholar 

  72. Dähne S, Leupold D (1966) Angew. Chem. Int. Ed. 5:984

    Article  Google Scholar 

  73. Miehe G, Süsse P, Kupcik V, Egert E, Nieger M, Kunz G, Gerke R, Knieriem B, Niemeyer M, Lüttke W (1991) Angew. Chem. Int. Ed. 30:964

    Article  Google Scholar 

  74. Serrano-Andrés L, Roos BO (1997) Chem. Eur. J 3:717

    Article  Google Scholar 

  75. Jacquemin D, Preat J, Wathelet V, Perpète EA (2006) J. Chem. Phys. 124:074104

    Article  CAS  Google Scholar 

  76. Jacquemin D, Preat J, Wathelet V, Fontaine M, Perpète EA (2006) J. Am. Chem. Soc. 128:2072

    Article  CAS  Google Scholar 

  77. Perpète EA, Jacquemin D (2009) J. Mol. Struct. Theochem. 914:100

    Article  CAS  Google Scholar 

  78. Yamazaki S, Sobolewski AL, Domcke W (2011) Phys. Chem. Chem. Phys. 13:1618

    Article  CAS  Google Scholar 

  79. Glowacki ED, Voss G, Sariciftci NS (2013) Adv. Mater. 25:6783

    Article  CAS  Google Scholar 

  80. Pina J, Seixas-de Melo JS, Eckert A, Scherf U (2015) J. Mater. Chem. A 3:6373

    Article  CAS  Google Scholar 

  81. Fukumoto H, Nakajima H, Kojima T, Yamamoto T (2014) Materials 7:2030

    Article  CAS  Google Scholar 

  82. Pramodini S, Poornesh P (2014) Opt. Laser Technol. 63:114

    Article  CAS  Google Scholar 

  83. Glowacki ED, Apaydin DH, Bozkurt Z, Monkowius U, Demirak K, Tordin E, Himmelsbach M, Schwarzinger C, Burian M, Lechner RT, Demitri N, Voss G, Sariciftci NS (2014) J. Mater. Chem. C 2:8089

    Article  CAS  Google Scholar 

  84. Robb MJ, Ku SY, Brunetti FG, Hawker CJ (2013) J. Polym. Sci. A Polym. Chem. 51:1263

    Article  CAS  Google Scholar 

  85. Becke AD (1993) J. Chem. Phys. 98:5648

    Article  CAS  Google Scholar 

  86. Yanai T, Tew DP, Handy NC (2004) Chem. Phys. Lett. 393:51

    Article  CAS  Google Scholar 

  87. Zhao Y, Schults NE, Truhlar DG (2006) J. Chem. Theory Comput. 2:364

    Article  CAS  Google Scholar 

  88. Zhao Y, Truhlar DG (2008) Theor. Chem. Acc. 120:215

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  91. Double and triple-\(\zeta\) basis sets of sns family, are available in the download section. http://dreams.sns.it Last visited: February 1 2015

  92. Carnimeo I, Puzzarini C, Tasinato N, Stoppa P, Charmet AP, Biczysko M, Cappelli C, Barone V (2013) J. Chem. Phys. 139:074310

    Article  CAS  Google Scholar 

  93. Barone V, Biczysko M, Bloino J (2014) Phys. Chem. Chem. Phys. 16:1759

    Article  CAS  Google Scholar 

  94. Bergner A, Dolg M, Kuchle W, Stoll H, Preuss H (1993) Mol. Phys. 80:1431

    Article  CAS  Google Scholar 

  95. Igelmann G, Stoll Preuss H (1988) Mol. Phys. 65:1321

    Article  CAS  Google Scholar 

  96. Tomasi J, Mennucci B, Cammi R (2005) Chem. Rev. 105:2999

    Article  CAS  Google Scholar 

  97. Cossi M, Scalmani G, Rega N, Barone V (2003) J. Comput. Chem. 24:669

    Article  CAS  Google Scholar 

  98. Baiardi A, Bloino J, Barone V (2015) J. Chem. Theory Comput. 11:3267

    Article  CAS  Google Scholar 

  99. Grimme S, Antony J, Ehrlich S, Krieg H (2010) J. Chem. Phys. 132:154104

    Article  CAS  Google Scholar 

  100. Grimme S (2011) WIREs Comput. Mol. Sci. 1:211

    Article  CAS  Google Scholar 

  101. Cossi M, Barone V (2001) J. Chem. Phys. 115:4708

    Article  CAS  Google Scholar 

  102. Beck ME (2005) Int. J. Quantum Chem. 101:683

    Article  CAS  Google Scholar 

  103. 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 HR, 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 Jr. JRJ. A. Peralta, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, 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 D.01, gaussian Inc. Wallingford CT

  104. Cui G, Thiel W (2012) Phys. Chem. Chem. Phys. 14:12378

    Article  CAS  Google Scholar 

  105. Huang K, Rhys A (1950) Proc. R. Soc. Lond. A Math. Phys. Eng. Sci. 204:406

    Article  CAS  Google Scholar 

  106. Fornaro T, Biczysko M, Monti S, Barone V (2014) Phys. Chem. Chem. Phys. 16:10112

    Article  CAS  Google Scholar 

  107. Fornaro T, Carnimeo I, Biczysko M (2015) J. Phys. Chem. A 119:5313

    Article  CAS  Google Scholar 

  108. Haucke G, Seidel B, Graness A (1987) J. Photochem. 37:139

    Article  CAS  Google Scholar 

  109. Gerke R, Fitjer L, Müller P (1999) Tetrahedron 55: 14429

    Article  CAS  Google Scholar 

  110. Wille E, Lüttke W (1971) Angew. Chem. Int. Ed. 10:803

    Article  CAS  Google Scholar 

  111. Haucke G, Graness G (1995) Angew. Chem. Int. Ed. 34:67

    Article  CAS  Google Scholar 

  112. Pummerer R, Marondel G (1960) Chem. Ber. 93:2834

    Article  CAS  Google Scholar 

  113. Clark RJH, Cooksey CJ (1999) N. J. Chem. 23:323

    Article  CAS  Google Scholar 

  114. Sadler PW (1956) J. Org. Chem. 21:316

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The research leading to these results has received funding from the European Union’s Seventh Framework Programme (FP7/2007–2013) under the Grant Agreement No. ERC-2012-AdG-320951-DREAMS. The high-performance computer facilities of the DREAMS center (http://dreams.sns.it) are acknowledged for providing computer resources. Alberto Baiardi is acknowledged for fruitful discussions and computations of Huang–Rhys factors.

Author information

Authors and Affiliations

  1. Scuola Normale Superiore di Pisa, Piazza dei Cavalieri 7, 56126, Pisa, Italy

    Vincenzo Barone, Camille Latouche & Andrea Pasti

  2. International Center of Quantum and Molecular Structures, Physics Department, Shanghai University, 99 Shangda Road, 200444, Shanghai, China

    Malgorzata Biczysko

Authors
  1. Vincenzo Barone
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Malgorzata Biczysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Camille Latouche
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrea Pasti
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vincenzo Barone.

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 & Energy from the Sun”.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (pdf 809 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Barone, V., Biczysko, M., Latouche, C. et al. Virtual eyes for technology and cultural heritage: towards computational strategy for new and old indigo-based dyes. Theor Chem Acc 134, 145 (2015). https://doi.org/10.1007/s00214-015-1753-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00214-015-1753-0

Keywords

Search

Navigation