Theoretical exploration of photoisomerization-switchable second-order nonlinear optical responses of two-dimendional λ- And w-shaped polyoxometalate derivatives of dithienylperfluorocyclopentene

Journal of Physical Chemistry A

Volumn 117, Issue 41, 2013, Pages 10783-10789

  Ma, Teng Ying ^a   Ma, Na Na ^a   Yan, Li Kai ^a   Zhang, Ting ^a   Su, Zhong Min ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FIRST HYPERPOLARIZABILITIES; INTRA-MOLECULAR CHARGE TRANSFER; PHOTOISOMERIZATION REACTION; POLYOXOMETALATES; SECOND-ORDER NONLINEAR OPTICAL; SECOND-ORDER NONLINEAR OPTICAL PROPERTY; SWITCHING BEHAVIORS; TIME-DEPENDENT DFT;

CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY;

OXIDES;

EID: 84886876810     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp407314a     Document Type: Article

References (64)

1. Marks, T. J.; Ratner, M. A. Design, Synthesis, and Properties of Molecule-Based Assemblies with Large Second-Order Optical Nonlinearities Angew. Chem., Int. Ed. Engl. 1995, 34, 155-173
2. Dalton, L. R.; Harper, A. W.; Ghosn, R.; Steier, W. H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen, AK.-Y.; Shea, K. J. Synthesis and Processing of Improved Organic Second-Order Nonlinear Optical Materials for Applications in Photonics Chem. Mater. 1995, 7, 1060-1081
3. Di Bella, S.; Fragalà, I.; Ledoux, I.; Diaz-Garcia, M. A.; Marks, T. J. Synthesis, Characterization, Optical Spectroscopic, Electronic Structure, and Second-Order Nonlinear Optical (NLO) Properties of a Novel Class of Donor-Acceptor Bis(salicylaldiminato)nickel(II) Schiff Base NLO Chromophores J. Am. Chem. Soc. 1997, 119, 9550-9557
4. Szacilowski, K. Digital Information Processing in Molecular Systems Chem. Rev. 2008, 108, 3481-3548
5. Feringa, B. L.; van Delden, R. A.; Koumura, N.; Geertsema, E. M. Chiroptical Molecular Switches Chem. Rev. 2000, 100, 1789-1816
6. Pease, A. P.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. P.; Heath, J. R. Switching Devices Based on Interlocked Molecules Acc. Chem. Res. 2001, 34, 433-444
7. 11 Bits per Square Centimeter Nature 2007, 445, 414-417
8. Green, K. A.; Cifuentes, M. P.; Corkery, T. C.; Samoc, M.; Humphrey, M. G. Switching the Cubic Nonlinear Optical Properties of an Electro-, Halo-, and Photochromic Ruthenium Alkynyl Complex Across Six States Angew. Chem., Int. Ed. 2009, 48, 7867-7870
9. Ishihara, S.; Hill, J. P.; Shundo, A.; Richards, G. J.; Labuta, J.; Ohkubo, K.; Fukuzumi, S.; Sato, A.; Elsegood, M. R. J.; Teat, S. J. Reversible Photoredox Switching of Porphyrin-Bridged Bis-2, 6-di-tert-butylphenols J. Am. Chem. Soc. 2011, 133, 16119-16126
10. He, B.; Wenger, O. S. Photoswitchable Organic Mixed Valence in Dithienylcyclopentene Systems with Tertiary Amine Redox Centers J. Am. Chem. Soc. 2011, 133, 17027-17036
11. Gorodetsky, B.; Samachetty, H. D.; Donkers, R. L.; Workentin, M. S.; Branda, N. R. Reductive Electrochemical Cyclization of a Photochromic 1,2-Dithienylcyclopentene Dication Angew. Chem., Int. Ed. 2004, 43, 2812-2815
12. Samoc, M.; Gauthier, N.; Cifuentes, M. P.; Paul, F.; Lapinte, C.; Humphrey, M. G. Electrochemical Switching of the Cubic Nonlinear Optical Properties of an Aryldiethynyl-Linked Heterobimetallic Complex between Three Distinct States Angew. Chem., Int. Ed. 2006, 45, 7376-7379
13. Malaun, M.; Reeves, Z. R.; Paul, R. L.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D.; Asselberghs, I.; Claysb, K.; Persoons, A. Reversible Switching of the First Hyperpolarisability of an NLO-Active Donor-Acceptor Molecule Based on Redox Interconversion of the Octamethylferrocene Donor Unit Chem. Commun. 2001, 49-50
14. Crano, J. C.; Guglielmetti, R. J. Organic Photochromic and Thermochromic Compounds; Plenum Press: New York, 1999.
15. Dulic, D.; van derMolen, S. J.; Kudernac, T.; Jonkman, H. T.; deJong, J. J. D.; Bowden, T. N.; van Esch, J.; Feringa, B. L.; van Wees, B. J. One-Way Optoelectronic Switching of Photochromic Molecules on Gold Phys. Rev. Lett. 2003, 91, 207-402
16. Katsonis, N.; Kudernac, T.; Walko, M.; van der Molen, S. J.; van Wees, B. J.; Feringa, B. L. Reversible Conductance Switching of Single Diarylethenes on a Gold Surface Adv. Mater. 2006, 18, 1397-1400
17. van der Molen, S. J.; Liao, J.; Kudernac, T.; Augustsson, J. S.; Bernard, L.; Calame, M.; vanWees, B. J.; Feringa, B. L.; Schönenberger, C. Light-Controlled Conductance Switching of Ordered Metal-Molecule-Metal Devices Nano Lett. 2009, 9, 76-80
18. Zhuang, M.; Ernzerhof, M. Reversibility and Transport Properties of Dithienylethene Photoswitches J. Chem. Phys. 2009, 130, 114704-114711
19. Malyal, J. P.; Gosse, I.; Morand, J. P.; Lapouyade, R. Photoswitching of Cation Complexation with a Monoaza-Crown Dithienylethene Photochrome J. Am. Chem. Soc. 2002, 124, 904-905
20. Irie, M.; Lifka, T.; Kobatake, S.; Kato, N. Photochromism of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in a Single-Crystalline Phase J. Am. Chem. Soc. 2000, 122, 4871-4876
21. Liu, C. C.; Su, Z. M.; Guan, X. H.; Muhammad, S. Redox and Photoisomerization Switching the Second-Order Nonlinear Optical Properties of a Tetrathiafulvalene Derivative Across Six Dtates: A DFT Study J. Phys. Chem. C 2011, 115, 23946-23954
22. Mayer, C. R.; Cabuil, V.; Lalot, T.; Thouvenot, R. Incorporation of Magnetic Nanoparticles in New Hybrid Networks Based on Heteropolyanions and Polyacrylamide Angew. Chem., Int. Ed. 1999, 38, 3672-3675
23. Yan, L. K.; Su, Z. M.; Zhuang, J.; Liu, C. G.; Sun, C. C. Theoretical Study on the Considerable Second-Order Nonlinear Optical Properties of Naphthylimido -Substituted Hexamolybdates J. Phys. Chem. A 2008, 112, 9919-9923
24. Shroden, R. C.; Blanford, C. F.; Melde, B. J.; Johnson, B. J. S.; Stein, A. Direct Synthesis of Ordered Macroporous Silica Materials Functionalized with Polyoxometalate Clusters Chem. Mater. 2001, 13, 1074-1081
25. Pope, M. T.; Muüller, A. Polyoxometalate Chemistry: An Old Field with New Dimensions in Several Disciplines Angew. Chem., Int. Ed. Engl. 1991, 30, 34-48
26. Kazansky, L. P.; McGarvey, B. R. McGarvey, NMR and EPR Spectroscopies and Electron Density Distribution in Polyoxoanions Coord. Chem. Rev. 1999, 188, 157-210
27. Mizuno, N.; Yamaguchi, K.; Kamata, K. Epoxidation of Olefins with Hydrogen Peroxide Catalyzed by Polyoxometalates Coord. Chem. Rev. 2005, 249, 1944-1956
28. Long, D. L.; Burkholder, E.; Cronin, L. Polyoxometalate Clusters, Nanostructures and Materials: From Self Assembly to Designer Materials and Devices Chem. Soc. Rev. 2007, 36, 105-121
29. Xu, L.; Wang, E. B.; Li, Z.; Kurth, D. G.; Du, X. G.; Zhang, H. Y.; Qin, C. Preparation and Nonlinear Optical Properties of Ultrathin Composite Films Containing Both a Polyoxometalate Anion and a Binuclear Phthalocyanine New J. Chem. 2002, 26, 782-786
30. 2O (HMPA=Hexamethylphosphoramide) Inorg. Chem. 1996, 35, 4211-4217
31. Yan, L. K.; Yang, G. C.; Guan, W.; Su, Z. M.; Wang, R. S. Density Functional Theory Study on the First Hyperpolarizabilities of Organoimido Derivatives of Hexamolybdates J. Phys. Chem. B 2005, 109, 22332-22336
32. Gouzerh, P.; Proust, A. Main-Group Element, Organic, and Organometallic Derivatives of Polyoxometalates Chem. Rev. 1998, 98, 77-112
33. Proust, A.; Thouvenot, R.; Gouzerh, P. Functionalization of Polyoxometalates: Towards Advanced Applications in Catalysis and Materials Science Chem. Commun. 2008, 1837-1852
34. Wei, Y. G.; Xu, B. B.; Barnes, C. L.; Peng, Z. H. An Efficient and Convenient Reaction Protocol to Organoimido Derivatives of Polyoxometalates J. Am. Chem. Soc. 2001, 123, 4083-4084
35. Guan, W.; Yang, G. C.; Yan, L. K.; Su, Z. M. Prediction of Second-Order Optical Nonlinearity of Trisorganotin-Substituted β -Keggin Polyoxotungstate Inorg. Chem. 2006, 45, 7864-7868
36. Yang, G. C.; Guan, W.; Yan, L. K.; Su, Z. M.; Xu, L.; Wang, E. B. Theoretical Study on the Electronic Spectrum and the Origin of Remarkably Large Third-Order Nonlinear Optical Properties of Organoimide Derivatives of Hexamolybdates J. Phys. Chem. B 2006, 110, 23092-23098
37. Wong, M. S.; Bosshard, C.; Pan, F.; Günter, P. Non-Classical Donor-Acceptor Chromophores for Second Order Nonlinear Optics Adv. Mater. 1996, 8, 677-680
38. Yamamoto, H.; Katogi, S.; Watanabe, T.; Sato, H.; Miyata, S.; Hosomi, T. New Molecular Design Approach for Noncentrosymmetric Crystal Structures: Lambda (Λ)-Shaped Molecules for Frequency Doubling Appl. Phys. Lett. 1992, 60, 935-937
39. Kuo, W. J.; Hsiue, G. H.; Jeng, R. J.; Novel Guest-Host, N. L. O. Poly(ether imide) Based on a Two-Dimensional Carbazole Chromophore with Sulfonyl Acceptors Macromolecules 2001, 34, 2373-2384
40. Di Bella, S.; Fragalà, I.; Ledoux, I.; Zyss, J. Dipolar Donor-Acceptor-Substituted Schiff Base Complexes with Large Off-Diagonal Second-Order Nonlinear Optical Tensor Components Chem.-Eur. J. 2001, 7, 3738-3743
41. Ostroverkhov, V.; Petschek, R. G.; Singer, K. D.; Twige, R. J. Λ-Like Chromophores for Chiral Non-Linear Optical Materials Chem. Phys. Lett. 2001, 340, 109-115
42. Liu, Y. J.; Liu, Y.; Zhang, D. J.; Hu, H. Q.; Liu, C. B. Theoretical Investigation on Second-Order Nonlinear Optical Properties of (Dicyanomethylene)-pyran Derivatives J. Mol. Struct. 2001, 570, 43-51
43. Van Elshocht, S.; Verbiest, T.; Kauranen, M.; Ma, L.; Cheng, H.; Musick, K. Y.; Pu, L.; Persoons, A. Chiral 1,1′-Binaphthyl-Based Helical Polymers as Nonlinear Optical Materials Chem. Phys. Lett. 1999, 309, 315-320
44. Wolff, J. J.; Längle, D.; Hillenbrand, D.; Wortmann, R.; Matschiner, R.; Glania, C.; Krämer, P. Dipolar NLO-Phores with Large Off-Diagonal Components of the Second-Order Polarizability Tensor Adv. Mater. 1997, 9, 138-143
45. Wortmann, R.; Krämer, P.; Glania, C.; Lebus, S.; Detzer, N. Deviations from Kleinman Symmetry of the Second-Order Polarizability Tensor in Molecules with Low-Lying Perpendicular Electronic Bands Chem. Phys. 1993, 173, 99-108
46. Wortmann, R.; Glania, C.; Krämer, P.; Matschiner, R.; Wolff, J. J.; Kraft, S.; Treptow, B.; Barbu, E.; Längle, D.; Görlitz, G. Nondipolar Structures With Threefold Symmetry For Nonlinear Optics Chem.-Eur. J. 1997, 3, 1765-1773
47. Rao, V. P.; Jen, A K.-Y.; Cai, Y. M. Achieving Excellent Tradeoffs Among Optical, Chemical and Thermal Properties in Second-Order Nonlinear Optical Chromophores Chem. Commun. 1996, 1237-1238
48. Ma, N. N.; Yang, G. C.; Sun, S. L.; Liu, C. G.; Qiu, Y. Q. Computational Sstudy on Second-Order Nonlinear Optical (NLO) Properties of a Novel Class of Two-Dimensional Λ- and W-Shaped Sandwich Metallocarborane-Containing Chromophores J. Organomet. Chem. 2011, 696, 2380-2387
49. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
50. Lee, C.; Yang, W.; Parr, R. G. Development of the Colic-Salvetti Correlationenergy Formula into a Functional of the Electron Density Phys. Rev. B. 1988, 37, 785-789
51. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frishch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
52. 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
53. Dehu, C.; Eyers, F.; Bredas, J. L. Donor-acceptor Diphenylacetylenes: Geometric Structure, Electronic Structure, and Second-Order Nonlinear Optical Properties J. Am. Chem. Soc. 1993, 115, 6198-6206
54. Sim, F.; Chin, S.; Dupuis, M.; Rice, J. E. Electron Correlation Effects in Hyperpolarizabilities of P-Nitroaniline J. Phys. Chem. 1993, 97, 1158-1163
55. Buckingham, A. D. Permanent and Induced Molecular Moments and Long-Rangeintermolecular Forces Adv. Chem. Phys. 1967, 12, 107-142
56. Mclean, A. D.; Yoshimine, M. Theory of Molecular Polarizabilities J. Chem. Phys. 1967, 47, 1927-1935
57. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A., Gaussian 09W, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
59. Wang, C. H.; Ma, N. N.; Sun, X. X.; Sun, S. L.; Qiu, Y. Q.; Liu, P. J. Modulation of the Second-Order Nonlinear Optical Properties of the Two-Dimensional Pincer Ru(II) Complexes: Substituent Effect and Proton Abstraction Switch J. Phys. Chem. A. 2012, 116, 10496-10506
60. Liu, C. G.; Guan, X. H. Redox and Photoisomerization Switching of the Second-Order Optical Nonlinearity of A Tetrathiafulvalene Derivative of Spiropyran Across Five States: A DFT Study Phys. Chem. Chem. Phys. 2012, 14, 5297-5306
61. Ma, T. Y.; Ma, N. N.; Yan, L. K.; Guan, W.; Su, Z. M. Theoretical Studies on the Photoisomerization-Switchable Second-Order Nonlinear Optical Responses of DTE-Linked Polyoxometalate Derivatives J. Mol. Graph. Model. 2013, 40, 110-115
62. Brasselet, S.; Zyss, J. Multipolar Molecules and Multipolar Fields: Probing and Controlling the Tensorial Nature of Nonlinear Molecular Media J. Opt. Soc. Am. B 1998, 15, 257-288
63. Zyss, J. Molecular Engineering Implications of Rotational Invariance in Quadratic Nonlinear Optics: From Dipolar to Octupolar Molecules and Materials J. Chem. Phys. 1993, 98, 6583-6599
64. Di Bella, S.; Fragala, L. Two-Dimensional Characteristics of the Second-Order Nonlinear Optical Response in Dipolar Donor-Acceptor Coordination Complexes N. J. Chem. 2002, 26, 285-290