Computational study of the one- and two-photon absorption properties of macrocyclic thiophene derivatives

Dyes and Pigments

Volumn 91, Issue 2, 2011, Pages 248-257

  Huang, Shuang ^a   Ren, Ai Min ^a,c   Zou, Lu Yi ^a   Zhao, Yang ^a   Guo, Jing Fu ^b,c   Feng, Ji Kang ^a  

^a JILIN UNIVERSITY   (China)

^b NORTHEAST NORMAL UNIVERSITY   (China)

^c NONE   (China)

Author keywords

Electronic structure; Macrocyclic thiophene derivatives; One photon absorption; TPA cross section; Two photon absorption; ZINDO method

Indexed keywords

MACROCYCLICS; ONE PHOTON ABSORPTION; TPA CROSS-SECTION; TWO-PHOTON ABSORPTIONS; ZINDO METHOD;

ABSORPTION; DENSITY FUNCTIONAL THEORY; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; LIGHT ABSORPTION; LUMINESCENCE OF ORGANIC SOLIDS; OSCILLATORS (ELECTRONIC); THIOPHENE; TWO PHOTON PROCESSES;

PHOTONS;

EID: 79958780731     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.02.005     Document Type: Review

References (42)

1. D.R. Kanis, M.A. Ratner, and T.J. Marks Design and construction of molecular assemblies with large second-order optical nonlinearities. Quantum chemical aspects Chemical Reviews 94 1994 195 242 (Pubitemid 24987843)
2. L.D. Boni, A.A. Andrade, D.S. Corrêa, D.T. Balogh, S.C. Zilio, and L. Misoguti Nonlinear absorption spectrum in MEH-PPV/chloroform solution: a competition between two-photon and saturated absorption processes Journal of Physical Chemistry B 108 2004 5221 5224
3. A. Margineanu, J. Hofkens, M. Cotlet, S. Habuchi, A. Stefan, and J.Q. Qu Photophysics of a water-soluble Rylene dye: comparison with other fluorescent molecules for biological applications Journal of Physical Chemistry B 108 2004 12242 12251
4. M. Göeppert-Mayer Über elementaraktemit zwei quantensprungen Annals of Physics 9 1931 273 295
5. W. Denk, J.H. Strickler, and W.W. Webb Two-photon laser scanning fluorescence microscopy Science 248 1990 73 76
6. J. Arnbjerg, A. Jimenez-Banzo, M.J. Paterson, S. Nonell, J.I. Borrell, and O. Christiansen Two-Photon absorption in tetraphenylporphycenes: are porphycenes better candidates than porphyrins for providing optimal optical properties for two-photon photodynamic therapy? Journal of American Chemistry Society 129 2007 5188 5199 (Pubitemid 46651397)
7. T.C. Lin, G.S. He, Q. Zheng, and P.N. Prasad Degenerate two-/three-photon absorption and optical power-limiting properties in femtosecond regime of a multi-branched chromophore Journal of Material Chemistry 16 2006 2490 2498
8. S. Maruo, O. Nakamura, and S. Kawata Three-dimensional microfabrication with two-photon-absorbed photopolymerization Optics Letters 22 1997 132 134 (Pubitemid 127593253)
9. D.A. Parthenopoulos, and P.M. Rentzepis Three-dimensional optical storage memory Science 245 1989 843 845
10. G.S. He, C.F. Zhao, J.D. Bhawalkar, and P.N. Prasad Two-photon pumped cavity lasing in novel dye doped bulk matrix rods Applied Physics Letters 67 1995 3703 3705
11. C.F. Zhao, G.S. He, J.D. Bhawalkar, C.K. Park, and P.N. Prasad Newly synthesized dyes and their polymer/glass composites for one- and two-photon pumped solid-state cavity lasing Chemistry of Materials 7 1995 1979 1983
12. Y. Wang, G.S. He, P.N. Prasad, and T. Goodson III Ultrafast dynamics in multibranched structures with enhanced two-photon absorption Journal of American Chemistry Society 127 2005 10128 10129 (Pubitemid 41045453)
13. X. Zhou, A.M. Ren, J.K. Feng, and X.J. Liu Theoretical study of two-photon absorption properties of a series of double-layer paracyclophane derivatives Journal of Physical Chemistry A 107 2003 1850 1858
14. Y. Zhao, A.M. Ren, J.K. Feng, and C.C. Sun Theoretical study of one-photon and two-photon absorption properties of perylene tetracarboxylic derivatives Journal of Chemical Physics 129 2008 014301
15. W.N. Leng, G.C. Bazan, and A.M. Kelley Solvent effects on resonance Raman and hyper-Raman scatterings for a centrosymmetric distyrylbenzene and relationship to two-photon absorption Journal of Chemical Physics 130 2009 044501
16. X. Li, Y.X. Zhao, T. Wang, M.Q. Shi, and F.P. Wu Coumarin derivatives with enhanced two-photon absorption cross-sections Dyes and Pigments 74 2007 108 112 (Pubitemid 44801277)
17. A. Abbotto, L. Beverina, R. Bozio, A. Facchetti, C. Ferrante, and G.A. Pagani Novel heteroaromatic-based multi-branched dyes with enhanced two-photon absorption activity Chemical Communication 7 2003 2144 2145 (Pubitemid 37076087)
18. M. Fakis, I. Fitilis, S. Stefanatos, P. Vellis, J. Mikroyannidis, and V. Giannetas The photophysics and two-photon absorption of a series of quadrupolar and tribranched molecules: the role of the edge substituent Dyes and Pigments 81 2009 63 68
19. J.S. Moore, and J. Zhang Efficient synthesis of nanoscale macrocyclic hydrocarbons Angewandte Chemie International Edition 31 1992 922 924
20. M. Bednarz, P. Reineker, E. Mena-Osteritz, and P. Baeuerle Optical absorption spectra of linear and cyclic thiophenes - selection rules manifestation Journal of Luminescence 110 2004 225 231
21. M. Williams-Harry, A. Bhaskar, G. Ramakrishna, T. Goodson III, M. Imamura, and A. Mawatari Giant thienylene-acetylene-ethylene macrocycles with large two-photon absorption cross section and semishape-persistence Journal of American Chemistry Society 130 2008 3252 3253 (Pubitemid 351456005)
22. N. Kiriy, V. Bocharova, A. Kiriy, M. Stamm, F.C. Krebs, and H.J. Adler Designing thiophene-based azomethine oligomers with tailored properties: self-assembly and charge carrier mobility Chemistry of Materials 16 2004 4765 4771
23. J. Nishida, T. Miyagawa, and Y. Yamashita Novel thiophene oligomers containing a redox active hexaarylethane unit Organic Letters 6 2004 2523 2526 (Pubitemid 39077759)
24. A. Bhaskar, G. Ramakrishna, K. Hagedorn, O. Varnavski, E.M. Osteritz, and P. Baluerle Enhancement of two-photon absorption cross-section in macrocyclic thiophenes with cavities in the nanometer regime Journal of Physical Chemistry B 111 2007 946 954
25. Huang S, Ren AM, Zou LY, Zhao Y, Guo JF, Feng JK. Computational study of the electronic structures, UV-Vis spectra and static second-order nonlinear optical susceptibilities of macrocyclic thiophene derivatives. submitted for publication.
26. J. Casadoa, M.Z. Zgierski, G. Fuhrmann, P.B. Juan, and J.T.L. Navarreteb Structural implications of ring shape, dimension, and metal atom insertion in nanosized cyclic oligothiophenes: joint Raman and density functional theory study Journal of Chemical Physics 125 2006 044518
27. G.L. Fuhrmann Synthesis and characterization of oligothiophene - based fully π-conjugated macrocycles the department of organic chemistry II 2006 University of Ulm Germany
28. T. Kogej, D. Beljonne, F. Meyers, J.W. Perry, S.R. Marder, and J.L. Brédas Mechanisms for enhancement of two-photon absorption in donor-acceptor conjugated chromophores Chemical Physics Letters 298 1998 1 6 (Pubitemid 128340329)
29. B.J. Orr, and J.F. Ward Perturbation theory of the non-linear optical polarization of an isolated system Molecular Physics 20 1971 513 526
30. D.M. Bishop, J.M. Luis, and B. Kirtman Vibration and two-photon absorption Journal of Chemical Physics 116 2002 9729 9739 (Pubitemid 34690625)
31. D. Beljonne, W. Wenseleers, E. Zojer, Z. Shuai, H. Vogel, and S.J.K. Pond Role of dimensionality on the two-photon absorption response of conjugated molecules: the case of octupolar compounds Advanced Functional Materials 12 2002 631 641
32. Y. Zhao, and D.G. Truhlar Hybrid meta density functional theory methods for thermochemistry, thermochemical kinetics, and noncovalent interactions: the MPW1B95 and MPWB1K models and comparative assessments for hydrogen bonding and van der waals interactions Journal of Physical Chemistry A 108 2004 6908 6918
33. Y. Zhao, and D.G. Truhlar Benchmark databases for nonbonded interactions and their use to test density functional theory Journal of Chemical Theory and Computation 1 2005 415 432
34. J.P. Perdew P. Ziesche, H. Eschig, Electronic structure of solids '91 1991 Akademie Verlag Berlin p11
35. A.D. Becke Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing Journal of Chemical Physics 104 1996 1040 1046 (Pubitemid 126747264)
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03 (Revision D02) 2003 Gaussian Inc. Pittsburgh, PA
37. W.P. Anderson, W.D. Edwards, and M.C. Zerner Calculated spectra of hydrated ions of the first transition-metal series Inorganic Chemistry 25 1986 2728 2732
38. X.B. Zhang, J.K. Feng, A.M. Ren, and C.C. Sun Theoretical study of two-photon absorption properties of a series of ferrocene-based chromophores Journal of Physical Chemistry A 110 2006 12222 12230
39. S. Huang, A.M. Ren, Z. Li, Y. Zhao, and C.G. Min Theoretical study on structures and UV-Vis spectra of macrocyclic thiophene derivatives Chemical Journal of Chinese Universities 3 2010 553 558
40. G. Fuhrmann, T. Debaerdemaeker, and P. Bäuerle C-C bond formation through oxidatively induced elimination of platinum complexes - a novel approach towards conjugated macrocycles Chemical Communications 2003 948 949 (Pubitemid 36469643)
41. J. Kromer, I. Rios-Carreras, G. Fuhrmann, C. Musch, M. Wunderlin, and T. Debaerdemaeker Synthesis of the first fully alpha-conjugated macrocyclic oligothiophenes cyclo [n] thiophenes with tunable cavities in the nanometer regime Angewandte Chemie-International Edition 39 2000 3481 3486
42. S.A. Hilderbrand, and R. Weissleder Near-infrared fluorescence: application to in vivo molecular imaging Current Opinion in Chemical Biology 14 2010 71 79