Photochromic and nonlinear optical properties of fulgides: A density functional theory study

Computational and Theoretical Chemistry

Volumn 1022, Issue , 2013, Pages 82-85

  Garza, Alejandro J ^a   Osman, Osman I ^b   Wazzan, Nuha A ^b   Khan, Sher B ^b   Scuseria, Gustavo E ^a,b   Asiri, Abdullah M ^b  

^a RICE UNIVERSITY   (United States)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Fulgides; Long range corrected DFT; Photochromic and nonlinear optical (NLO) properties

Indexed keywords

EID: 84884403114     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2013.08.021     Document Type: Article

References (43)

1. Hirshberg Y. Reversible formation and eradication of colors by irradiation at low temperatures. A photochemical memory model. J. Am. Chem. Soc. 1956, 78:2304-2312.
2. Irie M. Dyarilethenes for memories and switches. Chem. Rev. 2000, 100:1685-1716.
3. Kawata S., Kawata Y. Three-dimensional optical data storage using photochromic materials. Chem. Rev. 2000, 100:1777-1788.
4. Tian H., Yang S. Recent progresses on diarylethene based photochromic switches. Chem. Soc. Rev. 2004, 33:85-97.
5. Dvornikov A.S., Walker E.P., Rentzepis P.M. Two-photon three-dimensional optical storage memory. J. Phys. Chem. A 2009, 113:13633-13644.
6. Heller H.G., Langan J.R. Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene) (isopropylidene)succinic anhydride as a simple convenient chemical actinometer. J. Chem. Soc., Perkin Trans. 1981, 2:341-343.
7. Heller H.G. Photochromics for the future. Electronic Materials from Silicon to Organics 1991, 471-483. Plenum Press, New York. L.S. Miller (Ed.).
8. Asiri A.M. Photochromic properties of a vacuum-deposited film of (E)-dicyclopropylmethylene-(2,5-dimethyl-3-furylethyldiene)-succinic anhydride. J. Photochem. Photobiol. A: Chem. 2001, 146:133-135.
9. Bahajaj A.A., Asiri A.M. Photochromic properties of (E)-dicyclopropyl-methylene-(2,5-dimethyl-3-furylethylidene)-succinic anhydride doped in PMMA polymer film. Opt. Mater. 2006, 28:1064-1067.
10. S.R. Marder, J.E. Sohn, G.D. Stucky, Materials for non-linear optics: chemical perspectives, in: ACS symposium series, vol. 45, Washington, DC, 1991.
11. Boyd R.W. Nonlinear Optics 1992, Academic Press, New York.
12. Marder S.R. Organic nonlinear optical materials: where we have been and where we are going. Chem. Commun. 2006, 2:131-134.
13. Oudar J.L., Chemla D.S. Hyperpolarizabilities of the nitroanilines and their relations to the excited state dipole moment. J. Chem. Phys. 1977, 66:2664-2668.
14. M. Hurst et al., Organic materials for nonlinear optics, in: R.A. Hann, D. Bloor (Eds.), The royal Society of Chemistry, London, 1989.
15. Kanis D.R., Ratner M.A., Marks T.J. Design and construction of molecular assemblies with large second-order optical nonlinearities. Quantum chemical aspects. Chem. Rev. 1994, 94:195-242.
16. Savin A., Flad H. Density functionals for the Yukawa electron-electron interaction. Int. J. Quantum Chem. 1995, 56:327-332.
17. Iikura H., Tsuneda T., Yanai T., Hirao K. A long-range correction scheme for generalized-gradient-approximation exchange functionals. J. Chem. Phys. 2001, 115:3540-3544.
18. Yanai T., Tew D.P., Handy N.C. A new hybrid exchange correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem. Phys. Lett. 2004, 393:51-57.
19. Vydrov O.A., Heyd J., Krukau A.V., Scuseria G.E. Importance of short-range versus long-range Hartree-Fock exchange for the performance of hybrid density functionals. J. Chem. Phys. 2006, 125:074106.
20. Vydrov O.A., Scuseria G.E. Assessment of a long-range corrected hybrid functional. J. Chem. Phys. 2006, 125:234109.
21. * transitions in organic dyes. J. Chem. Phys. 2007, 127:094102.
22. Tawada Y., Tsuneda T., Yanagisawa S., Yanai T., Hirao K. A long-range-corrected time-dependent density functional theory. J. Chem. Phys. 2004, 120:8425-8433.
23. Kamiya M., Sekino H., Tsuneda T., Hirao K. Nonlinear optical property calculations by the long-range-corrected coupled-perturbed KohnSham method. J. Chem. Phys. 2005, 122:234111.
24. Jacquemin D., Perpète E.A., Scuseria G.E., Ciofini I., Adamo C. Modelling the UV/visible spectrum of tetrakis(phenylethynyl) benzene. J. Chem. Theor. Comput. 2008, 4:123-127.
25. Perpète E.A., Jacquemin D., Adamo C., Scuseria G.E. Chem. Phys. Lett. 2008, 456:101.
26. Jacquemin D., Perpète E.A., Scuseria G.E., Ciofini I., Adamo C. Extensive TD-DFT investigation of the first electronic transition in substituted azobenzenes. Chem. Phys. Lett. 2008, 465:226-229.
27. Song J., Watson M.A., Sekino H., Hirao K. Nonlinear optical property calculations of polyynes with long-range corrected hybrid exchange-correlation functionals. J. Chem. Phys. 2008, 129:024117.
28. Zaleśny R., Bulik I.W., Bartkowiak W., Luis J.M., Avramopoulos A., Papadopoulos M.G., Krawczyk P. Electronic and vibrational contributions to first hyperpolarizability of donor-acceptor-substituted azobenzene. J. Chem. Phys. 2010, 133:244308.
29. de Wergifosse M., Champagne B. Electron correlation effects on the first hyperpolarizability of pushpull π-conjugated systems. J. Chem. Phys. 2011, 134:074113.
30. Garza A.J., Scuseria G.E., Khan S.B., Asiri A.M. Assessment of long-range corrected functionals for the prediction of non-linear optical properties of organic materials. Chem. Phys. Lett. 2013, 575:122-125.
31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian Inc., Wallingford, CT, 2009 (Gaussian 09, Revision B.1).
32. Suponitsky K.Y., Tafur S., Masunov A.E. Applicability of hybrid density functional theory methods to calculation of molecular hyperpolarizability. J. Chem. Phys. 2008, 129:044109.
33. Garza A.J., Osman O.I., Scuseria G.E., Wazzan N.A., Khan S.B., Asiri A.M. Nonlinear optical properties of DPO and DMPO: a theoretical and computational study. Theor. Chem. Acc. 2013, 132:1384.
34. Hoffmann R., Woodward R.B. Selection rules for concerted cycloaddition reactions. J. Am. Chem. Soc. 1965, 87:2046-2048.
35. Jacquemin D., Perpète E.A., Medved M., Scalmani G., Frisch M.J., Kobayashi R., Adamo C. Assessment of the efficiency of long-range corrected functions for some properties of large compounds. J. Chem. Phys. 2007, 126:191108.
36. Patel P.D., Masunov A.E. Theoretical study of photochromic compounds. 1. Bond length alternation and absorption spectra for the open and closed forms of 29 diarylethene derivatives. J. Phys. Chem. A 2009, 113:8409-8414.
37. Champagne B., Perpete E.A., van Gisbergen S.J.A., Baerends E.J., Snijders J.G., Soubra-Ghaoui C., Robins K.A., Kirtman B. Assessment of conventional density functional schemes for computing the polarizabilities and hyperpolarizabilities of conjugated oligomers: an ab initio investigation of polyacetylene chains. J. Chem. Phys. 1998, 109:10489-10498.
38. Champagne B., Perpete E.A., Jacquemin D., A van Gisbergen S.J., Baerends E.J., Soubra-Ghaou C., Robins K.A., Kirtman B. Assessment of conventional density functional schemes for computing the dipole moment and (Hyper)polarizabilities of PushPull π-conjugated systems. J. Chem. Phys. 2000, 104:4755-4763.
39. Loboda O., Zaleśny R., Avramopoulos A., Luis J.M., Kirtman B., Tagmatarchis N., Reis H., Papadopoulos M.G. Linear and nonlinear optical properties of [60] fullerene derivatives. J. Phys. Chem. A 2009, 113:1159-1170.
40. van Faassen M., de Boeij R., van Leeuwen P.L., Berger J.A., Snijders J.G. Application of time-dependent current-density-functional theory to nonlocal exchange-correlation effects in polymers. J. Chem. Phys. 2003, 118:1044-1053.
41. Kirtman B., Lacivita V., Dovesi R., Reis H.J. Electric field polarization in conventional density functional theory: from quasilinear to two-dimensional and three-dimensional extended systems. J. Chem. Phys. 2011, 135:154101.
42. Thanthiriwatte K.S., Nalin de Silva K.M. Non-linear optical properties of novel fluorenyl derivatives-ab initio quantum chemical calculations. Theochem 2002, 617:169-175.
43. Asiri A.M., Khan S.A., Al-Amoudi M.S., Alamry K.A. Synthesis, characterization, absorbance, fluorescence and non linear optical properties of some donor acceptor chromophores. Bull. Korean Chem. Soc. 2012, 33:1900-1906.