Position isomerism on one and two photon absorption in multibranched chromophores: A TDDFT investigation

Journal of Chemical Theory and Computation

Volumn 6, Issue 11, 2010, Pages 3410-3426

  Katan, Claudine ^a   Blanchard Desce, Mireille ^a   Tretiak, Sergei ^b  

^a UNIVERSITÉ EUROPÉENNE DE BRETAGNE   (France)

^b CENTER FOR INTEGRATED NANOTECHNOLOGIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78149424116     PISSN: 15499618     EISSN: 15499626     Source Type: Journal    
DOI: 10.1021/ct1004406     Document Type: Article

References (77)

1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. Engl. 2001, 40, 2004
2. Qin, A.; Lam, J. W. Y.; Tang, B. Z. Click polymerization Chem. Rev. 2010, 39, 2522
3. Zhou, Z.; Fahrni, C. J. A Fluorogenic Probe for the Copper(I)-Catalyzed Azide-Alkyne Ligation Reaction: Modulation of the Fluorescence Emission via 3(n,π*)-1(π,π*) Inversion J. Am. Chem. Soc. 2004, 126, 886
4. Parent, M.; Mongin, O.; Kamada, K.; Katan, C.; Blanchard-Desce, M. New chromophores from click chemistry for two-photon absorption and tuneable photoluminescence Chem. Commun. 2005, 2029
5. Qin, A.; Jim, C. K. W.; Lu, W.; Lam, J. W. Y.; Häussler, M.; Dong, Y.; Sung, H. H. Y.; Williams, I. D.; Wong, G. K. L.; Tang, B. Z. Click Polymerization: Facile Synthesis of Functional Poly(aroyltriazole)s by Metal-Free, Regioselective 1,3-Dipolar Polycycloaddition Macromolecules 2007, 40, 2308
6. Jarowski, P. D.; Wu, Y.-L.; Schweizer, W. B.; Diederich, F. 1,2,3-Triazoles as Conjugative π-Linkers in Push-Pull Chromophores: Importance of Substituent Positioning on Intramolecular Charge-Transfer Org. Lett. 2008, 10, 3347
7. Qin, A.; Lam, J. W. Y.; Jim, C. K. W.; Zhang, L.; Yan, J.; Haüssler, M.; Liu, J.; Dong, Y.; Liang, D.; Chen, E.; Jia, G.; Tang, B. Z. Hyperbranched polytriazoles: Click polymerization, regioisomeric structure, light emission, and fluorescent patterning Macromolecules 2008, 41, 3808
8. Meudtner, Robert, M.; Ostermeier, M.; Goddard, R.; Limberg, C.; Hecht, S. Multifunctional ldquoClickatesrdquo as Versatile Extended Heteroaromatic Building Blocks: Efficient Synthesis via Click Chemistry, Conformational Preferences, and Metal Coordination Chem.-Eur. J. 2007, 13, 9834
9. Schweinfurth, D.; Hardcastle, K. I.; Bunz, U. H. F. 1,3-Dipolar cycloaddition of alkynes to azides. Construction of operationally functional metal responsive fluorophores Chem. Commun. 2008, 2203
10. Li, Z. a.; Yu, G.; Wu, W.; Liu, Y.; Ye, C.; Qin, J.; Li, Z. Nonlinear Optical Dendrimers from Click Chemistry: Convenient Synthesis, New Function of the Formed Triazole Rings, and Enhanced NLO Effects Macromolecules 2009, 42, 3864
11. Li, Z. a.; Yu, G.; Hu, P.; Ye, C.; Liu, Y.; Qin, J.; Li, Z. New Azo-Chromophore-Containing Hyperbranched Polytriazoles Derived from AB2Monomers via Click Chemistry under Copper(I) Catalysis Macromolecules 2009, 42, 1589
12. Xie, J.; Hu, L.; Shi, W.; Deng, X.; Cao, Z.; Shen, Q. Synthesis and nonlinear optical properties of hyperbranched polytriazole containing second-order nonlinear optical chromophore J. Polym. Sci., Part B: Polym. Phys. 2008, 46, 1140
13. Zoon, P. D.; Stokkum, I. H. M. v.; Parent, M.; Mongin, O.; Blanchard-Desce, M.; Brouwer, A. M. Fast photo-processes in triazole-based push-pull systems Phys. Chem. Chem. Phys. 2010, 12, 2706
14. Fréchet, J. M. J. Dendrimers and supramolecular chemistry Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4782
15. Sullivan, P. A.; Rommel, H.; Liao, Y.; Olbricht, B. C.; Akelaitis, A. J. P.; Firestone, K. A.; Kang, J.-W.; Luo, J.; Davies, J. A.; Choi, D. H.; Eichinger, B. E.; Reid, P. J.; Chen, A.; Jen, A. K. Y.; Robinson, B. H.; Dalton, L. R. Theory-guided design and synthesis of multichromophore dendrimers: An analysis of the electro-optic effect J. Am. Chem. Soc. 2007, 129, 7523
16. He, G. S.; Tan, L. S.; Zheng, Q.; Prasad, P. N. Multiphoton absorbing materials: Molecular designs, characterizations, and applications Chem. Rev. 2008, 108, 1245
17. Terenziani, F.; Katan, C.; Badaeva, E.; Tretiak, S.; Blanchard-Desce, M. Enhanced Two-Photon Absorption of Organic Chromophores: Theoretical and Experimental Assessments Adv. Mater. 2008, 20, 4641
18. Rumi, M.; Barlow, S.; Wang, J.; Perry, J. W.; Marder, S. R. Two-Photon Absorbing Materials and Two-Photon-Induced Chemistry. In Photoresponsive Polymers I; Advances in Polymer Science; Springer-Verlag: Berlin, 2008; Vol. 213, pp 1 - 95.
19. Pawlicki, M.; Collins, H. A.; Denning, R. G.; Anderson, H. L. Two-Photon Absorption and the Design of Two-Photon Dyes Angew. Chem., Int. Ed. Engl. 2009, 48, 3244
20. Specht, A.; Bolze, F.; Omran, Z.; Nicoud, J.-F.; Goeldner, M. Photochemical tools to study dynamic biological processes HFSP J. 2009, 3, 255
21. Kim, H. M.; Cho, B. R. Two-photon materials with large two-photon cross sections. Structure-property relationship Chem. Commun. 2009, 153
22. Joshi, M. P.; Swiatkiewicz, J.; Xu, F. M.; Prasad, P. N. Energy transfer coupling of two-photon absorption and reverse saturable absorption for enhanced optical power limiting Opt. Lett. 1998, 23, 1742
23. Chung, S. J.; Kim, K. S.; Lin, T. H.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. Cooperative enhancement of two-photon absorption in multi-branched structures J. Phys. Chem. B 1999, 103, 10741
24. Cho, B. R.; Son, K. H.; Lee, S. H.; Song, Y. S.; Lee, Y. K.; Jeon, S. J.; Choi, J. H.; Lee, H.; Cho, M. H. Two Photon Absorption Properties of 1,3,5-Tricyano-2,4,6-tris(styryl)benzene Derivatives J. Am. Chem. Soc. 2001, 123, 10039
25. Katan, C.; Terenziani, F.; Mongin, O.; Werts, M. H. V.; Porres, L.; Pons, T.; Mertz, J.; Tretiak, S.; Blanchard-Desce, M. Effects of (multi)branching of dipolar chromophores on photophysical properties and two-photon absorption J. Phys. Chem. A 2005, 109, 3024
26. Katan, C.; Terenziani, F.; Droumaguet, C. L.; Mongin, O.; Werts, M. H. V.; Tretiak, S.; Blanchard-Desce, M. Branching of dipolar chromophores: effects on linear and nonlinear optical properties Proc. SPIE, Int. Soc. Opt. Eng. 2005, 5935, 593503
27. Terenziani, F.; Morone, M.; Gmouh, S.; Blanchard-Desce, M. Linear and Two-Photon Absorption Properties of Interacting Polar Chromophores: Standard and Unconventional Effects ChemPhysChem 2006, 7, 685
28. Allain, C.; Schmidt, F.; Lartia, R.; Bordeau, G.; Fiorini-Debuisschert, C.; Charra, F.; Tauc, P.; Teulade-Fichou, M.-P. Vinyl-Pyridinium Triphenylamines: Novel Far-Red Emitters with High Photostability and Two-Photon Absorption Properties for Staining DNA ChemBioChem 2007, 8, 424
29. Terenziani, F.; Le Droumaguet, C.; Katan, C.; Mongin, O.; Blanchard-Desce, M. Effect of branching on two-photon absorption in triphenylbenzene derivatives ChemPhysChem 2007, 8, 723
30. Kim, H. M.; Seo, M. S.; Jeon, S.-J.; Cho, B. R. Two-photon absorption properties of hexa-substituted benzene derivatives. Comparison between dipolar and octupolar molecules Chem. Commun. 2009, 7422
31. Katan, C.; Tretiak, S.; Even, J. Two-photon transitions in triazole based quadrupolar and octupolar chromophores: a TD-DFT investigation Proc. SPIE, Int. Soc. 20 (10) 7712, 77123D
32. Drobizhev, M.; Karotki, A.; Dzenis, Y.; Rebane, A.; Suo, Z. Y.; Spangler, C. W. Strong cooperative enhancement of two-photon absorption in dendrimers J. Phys. Chem. B. 2003, 107, 7540
33. Yoo, J.; Yang, S. K.; Jeong, M. Y.; Ahn, H. C.; Jeon, S. J.; Cho, B. R. Bis-1,4(p-diarylaminostryl)-2,5-dicyanobenzene derivatives with large two-photon absorption cross-sections Org. Lett. 2003, 5, 645
34. Mongin, O.; Porres, L.; Katan, C.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Synthesis and two-photon absorption of highly soluble three-branched fluorenylene-vinylene derivatives Tetrahedron Lett. 2003, 44, 8121
35. Bartholomew, G. P.; Rumi, M.; Pond, S. J. K.; Perry, J. W.; Tretiak, S.; Bazan, G. C. Two-photon absorption in three-dimensional chromophores based on 2.2 -paracyclophane J. Am. Chem. Soc. 2004, 126, 11529
36. Varnavski, O.; Yan, X. Z.; Mongin, O.; Blanchard-Desce, M.; Goodson, T.; Goodson, T. Strongly interacting organic conjugated dendrimers with enhanced two-photon absorption J. Phys. Chem. C. 2007, 111, 149
37. Katan, C.; Tretiak, S.; Werts, M. H. V.; Bain, A. J.; Marsh, R. J.; Leonczek, N.; Nicolaou, N.; Badaeva, E.; Mongin, O.; Blanchard-Desce, M. Two-photon transitions in quadrupolar and branched chromophores: Experiment and theory J. Phys. Chem. B 2007, 111, 9468
38. Rumi, M.; Pond, S. J. K.; Meyer-Friedrichsen, T.; Zhang, Q.; Bishop, M.; Zhang, Y.; Barlow, S.; Marder, S. R.; Perry, J. W. Tetrastyrylarene Derivatives: Comparison of One- and Two-Photon Spectroscopic Properties with Distyrylarene Analogues J. Phys. Chem. C 2008, 112, 8061
39. Varnavski, O. P.; Ostrowski, J. C.; Sukhomlinova, L.; Twieg, R. J.; Bazan, G. C.; Goodson, T. Coherent Effects in Energy Transport in Model Dendritic Structures Investigated by Ultrafast Fluorescence Anisotropy Spectroscopy J. Am. Chem. Soc. 2002, 124, 1736
40. Parent, M. Ph.D. Thesis, University of Rennes, Rennes, France, 2008.
41. Blanchard-Desce and Coll. Unpublished.
42. Terenziani, F.; Painelli, A.; Katan, C.; Charlot, M.; Blanchard-Desce, M. Charge instability in quadrupolar chromophores: Symmetry breaking and solvatochromism J. Am. Chem. Soc. 2006, 128, 15742
43. Lambert, C.; Schmalzlin, E.; Meerholz, K.; Brauchle, C. Synthesis and nonlinear optical properties of three-dimensional phosphonium ion chromophores Chem.-Eur. J. 1998, 4, 512
44. Tretiak, S.; Chernyak, V.; Mukamel, S. Localized Electronic Excitations in Phenylacetylene Dendrimers J. Phys. Chem. B. 1998, 102, 3310
45. Poliakov, E. Y.; Chernyak, V.; Tretiak, S.; Mukamel, S. Exciton-scaling and optical excitations of self-similar phenylacetylene dendrimers J. Chem. Phys. 1999, 110, 8161
46. Chernyak, V.; Poliakov, E. Y.; Tretiak, S.; Mukamel, S. Two-exciton states and spectroscopy of phenylacetylene dendrimers J. Chem. Phys. 1999, 111, 4158
47. Beljonne, D.; Wenseleers, W.; Zojer, E.; Shuai, Z. G.; Vogel, H.; Pond, S. J. K.; Perry, J. W.; Marder, S. R.; Bredas, J. L. Role of dimensionality on the two-photon absorption response of conjugated molecules: The case of octupolar compounds Adv. Funct. Mater. 2002, 12, 631
48. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold J. Chem. Phys. 1998, 108, 4439
49. Furche, F.; Ahlrichs, R. Adiabatic time-dependent density functional methods for excited state properties J. Chem. Phys. 2002, 117, 7433
50. Grimme, S. Calculation of the electronic spectra of large molecules. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH Publishers: New York, 2004; Vol. 20, pp 153 - 218.
51. Dreuw, A.; Head-Gordon, M. Single-reference ab initio methods for the calculation of excited states of large molecules Chem. Rev. 2005, 105, 4009
52. Champagne, B.; Guillaume, M.; Zutterman, F. TDDFT investigation of the optical properties of cyanine dyes Chem. Phys. Lett. 2006, 425, 105
53. Miura, M.; Aoki, Y.; Champagne, B. Assessment of time-dependent density functional schemes for computing the oscillator strengths of benzene, phenol, aniline, and fluorobenzene J. Chem. Phys. 2007, 127 084103
54. Magyar, R. J.; Tretiak, S. Dependence of spurious charge-transfer excited states on orbital exchange in TDDFT: Large molecules and clusters J. Chem. Theory Comput. 2007, 3, 976
55. Jacquemin, D.; Wathelet, V.; Perpète, E. A.; Adamo, C. Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules J. Chem. Theory Comput. 2009, 5, 2420
56. Tretiak, S.; Chernyak, V. Resonant nonlinear polarizabilities in the time-dependent density functional theory J. Chem. Phys. 2003, 119, 8809
57. Masunov, A.; Tretiak, S. Prediction of two-photon absorption properties for organic chromophores using time-dependent density-functional theory J. Phys. Chem. B. 2003, 108, 899
58. Kobko, N.; Masunov, A.; Tretiak, S. Calculations of the third-order nonlinear optical responses in push-pull chromophores with a time-dependent density functional theory Chem. Phys. Lett. 2004, 392, 444
59. Kauffman, J. F.; Turner, J. M.; Alabugin, I. V.; Breiner, B.; Kovalenko, S. V.; Badaeva, E. A.; Masunov, A.; Tretiak, S. Two-photon excitation of substituted enediynes J. Phys. Chem. A. 2005, 110, 241
60. Badaeva, E. A.; Timofeeva, T. V.; Masunov, A.; Tretiak, S. Role of donor-acceptor strengths and separation on the two-photon absorption response of cytotoxic dyes: A TD-DFT study J. Phys. Chem. A. 2005, 109, 7276
61. Clark, A. E. Time-Dependent Density Functional Theory Studies of the Photoswitching of the Two-Photon Absorption Spectra in Stilbene, Metacyclophenadiene, and Diarylethene Chromophores J. Phys. Chem. A 2006, 110, 3790
62. Wu, C.; Tretiak, S.; Chernyak, V. Y. Excited states and optical response of a donor-acceptor substituted polyene: A TD-DFT study Chem. Phys. Lett. 2007, 433, 305
63. Katan, C.; Charlot, M.; Mongin, O.; Le Droumaguet, C. l.; Jouikov, V.; Terenziani, F.; Badaeva, E.; Tretiak, S.; Blanchard-Desce, M. Simultaneous Control of Emission Localization and Two-Photon Absorption Efficiency in Dissymmetrical Chromophores J. Phys. Chem. B 2010, 114, 3152
64. Cross-shaped chromophores consisting of four donor substituted branches linked to an aromatic core have already been investigated but show significant differences, e.g., in OPA spectra, and can well be described as a dimer of corresponding quadrupolar benchmarks. (38)
65. Ultrafast fluorescence spectroscopy has already been performed on a related carbon-cored tetramer. (39)
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.;; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
67. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
68. Martin, R. L. Natural transition orbitals J. Chem. Phys. 2003, 118, 4775
69. Kokalj, A. Computer graphics and graphical user interfaces as tools in simulations of matter at the atomic scale Comput. Mater. Sci. 2003, 28, 155
70. Mongin, O.; Porres, L.; Charlot, M.; Katan, C.; Blanchard-Desce, M. Synthesis, fluorescence, and two-photon absorption of a series of elongated rodlike and banana-shaped quadrupolar fluorophores: A comprehensive study of structure-property relationships Chem.-Eur. J. 2007, 13, 1481
71. Lu, D.; Chen, G.; Perry, J. W.; Goddard, W. A. Valence-Bond Charge-Transfer Model For Nonlinear-Optical Properties Of Charge-Transfer Organic-Molecules J. Am. Chem. Soc. 1994, 116, 10679
72. Barzoukas, M.; Blanchard-Desce, M. Molecular engineering of push-pull dipolar and quadrupolar molecules for two-photon absorption: A multivalence-bond states approach J. Chem. Phys. 2000, 113, 3951
73. Terenziani, F.; Sissa, C.; Painelli, A. Symmetry breaking in octupolar chromophores: Solvatochromism and electroabsorption J. Phys. Chem. B 2008, 112, 5079
74. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380
75. Basavoju, S.; Aitipamula, S.; Desiraju, G. R. Host-guest and network structures of some tetraphenylmethane derivatives CrystEngComm. 2004, 6, 120
76. Oldham, W. J.; Lachicotte, R. J.; Bazan, G. C. Synthesis, spectroscopy, and morphology of tetrastilbenoidmethanes J. Am. Chem. Soc. 1998, 120, 2987
77. Porres, L.; Mongin, O.; Katan, C.; Charlot, M.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Enhanced two-photon absorption with novel octupolar propeller-shaped fluorophores derived from triphenylamine Org. Lett. 2004, 6, 47