Photophysical properties of derivatives of 2-(2-Hydroxyphen-yl)-1,3,4- oxadiazole: A theoretical study

Journal of Physical Chemistry A

Volumn 117, Issue 34, 2013, Pages 8285-8292

  Jin, Ruifa ^a,b   Zhang, Jingping ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b Chifeng University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DISPLAY TECHNOLOGIES; ELECTROLUMINESCENCE MATERIALS; ELECTROLUMINESCENT EFFICIENCIES; ELECTRON TRANSPORT MATERIALS; ELECTRON TRANSPORTING; FLUORESCENCE WAVELENGTH; ORGANIC LIGHT EMITTING DIODES(OLEDS); PHOTOPHYSICAL PROPERTIES;

FLAT PANEL DISPLAYS; ORGANIC LIGHT EMITTING DIODES (OLED); THIOPHENE; TRANSPORT PROPERTIES;

ELECTROLUMINESCENCE;

EID: 84883382011     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp403643f     Document Type: Conference Paper

References (75)

1. Le, D. G.; Ormson, S. M.; Brown, R. G. Excited State Intramolecular Proton Transfer Part 2: Esipt to Oxygen Prog. React. Kinet. 1994, 19, 211-275
2. Dyrager, C.; Friberg, A.; Dahlén, K.; Maria Fridén-Saxin, M.; Börjesson, K.; Wilhelmsson, L. M.; Smedh, M.; Grøtli, M.; Luthman, K. 2,6,8-Trisubstituted 3-Hydroxychromone Derivatives as Fluorophores for Live-Cell Imaging Chem.-Eur. J. 2009, 15, 9417-9423
3. Patil, V. S.; Padalkar, V. S.; Phatangare, K. R.; Gupta, V. D.; Umape, P. G.; Sekar, N. Synthesis of New ESIPT-Fluorescein: Photophysics of pH Sensitivity and Fluorescence J. Phys. Chem. A 2012, 116, 536-545
4. 1 States J. Phys. Chem. A 2012, 116, 2109-2116
5. IV Derivatives with Schiff Bases: A Comparative Study of the Effect of Chelation from the Ultrafast to the Steady-State Time Scale J. Phys. Chem. A 2010, 114, 704-714
6. Ding, L.; Chen, X.; Fang, W. Ultrafast Asynchronous Concerted Excited-State Intramolecular Proton Transfer and Photodecarboxylation of o -Acetylphenylacetic Acid Explored by Combined CASPT2 and CASSCF Studies Org. Lett. 2009, 11, 1495-1498
7. Fita, P.; Urbańska, N.; Radzewicz, C.; Waluk, J. Ground- and Excited-State Tautomerization Rates in Porphycenes Chem.-Eur. J. 2009, 15, 4851-4856
8. Mosquera, M.; Penedo, J. C.; Rodriguez, M. C. R.; Rodriguez-Prieto, F. Photoinduced Inter- and Intramolecular Proton Transfer in Aqueous and Ethanolic Solutions of 2-(2′-Hydroxyphenyl)benzimidazole: Evidence for Tautomeric and Conformational Equilibria in the Ground State J. Phys. Chem. 1996, 100, 5398-7407
9. de Vivie-Riedle, R.; Waele, V. D.; Kurtz, L.; Riedle, E. Ultrafast Excited-State Proton Transfer of 2-(2′-Hydroxyphenyl)benzothiazole: Theoretical Analysis of the Skeletal Deformations and the Active Vibrational Modes J. Phys. Chem. A 2003, 107, 10591-10599
10. Chipem, F. A. S.; Krishnamoorthy, G. Comparative Theoretical Study of Rotamerism and Excited State Intramolecular Proton Transfer of 2-(2′-Hydroxyphenyl)benzimidazole, 2-(2′-Hydroxyphenyl)imidazo[4,5- b]pyridine, 2-(2′-Hydroxyphenyl)imidazo[4,5-c] pyridine and 8-(2′-Hydroxyphenyl)purine J. Phys. Chem. A 2009, 113, 12063-12070
11. Tong, H.; Zhou, G.; Wang, L.; Jing, X.; Wang, F.; Zhang, J. Novel Highly Selective Anion Chemosensors Based on 2,5-Bis(2-hydroxyphenyl)-1,3,4-oxadiazole Tetrahedron. Lett. 2003, 44, 131-134
12. Kim, T.-I.; Kang, H. J.; Han, G.; Chung, S. J.; Kim, Y. A Highly Selective Fluorescent ESIPT Probe for the Dual Specificity Phosphatase MKP-6 Chem. Commun. 2009, 5895-5897
13. Yi, Y.; Zhu, L.; Shuai, Z. Theoretical Designs of Molecular Photonics Materials Macromol. Theory Simul. 2008, 17, 12-22
14. May, F.; Al-Helwi, M.; Baumeier, B.; Kowalsky, W.; Fuchs, E.; Lennartz, C.; Andrienko, D. Design Rules for Charge-Transport Efficient Host Materials for Phosphorescent Organic Light-Emitting Diodes J. Am. Chem. Soc. 2012, 134, 13818-13822
15. Lee, S. Y.; Yasuda, T.; Nomura, H.; Adachi, C. High-Efficiency Organic Light-Emitting Diodes Utilizing Thermally Activated Delayed Fluorescence from Triazine-Based Donor-Acceptor Hybrid Molecules Appl. Phys. Lett. 2012, 101, 093306
16. Kim, J. Y.; Yokoyama, D.; Adachi, C. Horizontal Orientation of Disk-like Hole Transport Molecules and Their Application for Organic Light-Emitting Diodes Requiring a Lower Driving Voltage J. Phys. Chem. C 2012, 116, 8699-8706
17. Rogach, A. L.; Gaponik, N.; Lupton, J. M.; Bertoni, C.; Gallardo, D. E.; Dunn, S.; Li Pira, N.; Paderi, M.; Repetto, P.; Romanov, S. G. Light-Emitting Diodes with Semiconductor Nanocrystals Angew. Chem., Int. Ed. 2008, 47, 6538-6549
18. Hlawacek, G.; Puschnig, P.; Frank, P.; Winkler, A.; Ambrosch-Drax, C.; Teichert, C. Characterization of Step-Edge Barriers in Organic Thin-Film Growth Science. 2008, 321, 108-111
19. Keck, J.; Kramer, H. E. A.; Port, H.; Hirsch, T.; Fischer, P.; Rytz, G. Investigations on Polymeric and Monomeric Intramolecularly Hydrogen-Bridged UV Absorbers of the Benzotriazole and Triazine Class J. Phys. Chem. 1996, 100, 14468-14475
20. Douhal, A.; Sastre, R. Room-Temperature Triple Proton Transfer of 7-Hydroxyquinoline and Stabilization of Its Ground-State Keto Tautomer in a Polymeric Matrix Chem. Phys. Lett. 1994, 219, 91-94
21. Yokoyama, Y. Fulgides for Memories and Switches Chem. Rev. 2000, 100, 1717-1740
22. Tamai, N.; Miyasaka, H. Ultrafast Dynamics of Photochromic Systems Chem. Rev. 2000, 100, 1875-1890
23. Purkayastha, P.; Chattopadhyay, N. Rotamerisation and Intramolecular Proton Transfer of 2-(2′-Hydroxyphenyl)oxazole, 2-(2′-Hydroxyphenyl) imidazole and 2-(2′-Hydroxyphenyl)thiazole: A Theoretical Study J. Mol. Struct. 2002, 604, 87-99
24. Coe, J. D.; Levine, B. G.; Martinez, T. J. Ab Initio Molecular Dynamics of Excited-State Intramolecular Proton Transfer Using Multireference Perturbation Theory J. Phys. Chem. A 2007, 111, 11302-11310
25. Coe, J.; Martinez, T. J. Competitive Decay at Two- and Three-State Conical Intersections in Excited-State Intramolecular Proton Transfer J. Am. Chem. Soc. 2005, 127, 4560-4561
26. Doltsinis, N. L. Excited State Proton Transfer and Internal Conversion in o -Hydroxybenzaldehyde: New Insights from Non-Adiabatic ab Initio Molecular Dynamics Mol. Phys. 2004, 102, 499-506
27. Wu, Y.; Batista, V. Matching-Pursuit Split-Operator Fourier-Transform Simulations of Excited-State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)-oxazole J. Chem. Phys. 2006, 124, 224305-224313
28. Gaenko, A. V.; Devarajan, A.; Tselinskii, I. V.; Ryde, U. Structural and Photoluminescence Properties of Excited State Intramolecular Proton Transfer Capable Compounds-Potential Emissive and Electron Transport Materials J. Phys. Chem. A 2006, 110, 7935-7942
29. Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M. Excited State Intramolecular Proton Transfer Reaction and Luminescent Properties of the ortho -Hydroxy Derivatives of 2,5-Diphenyl-1,3,4-oxadiazole J. Phys. Org. Chem. 2000, 13, 253-265
30. Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M.; Skripkina, V. T.; Shershukov, V. M. Radiationless Deactivation of the Excited Phototautomer Form and Molecular Structure of ESIPT-Compounds Photochem. Photobiol. Sci. 2002, 1, 92-99
31. Yang, Z.; Yang, S.; Zhang, J. Ground- and Excited-State Proton Transfer and Rotamerism in 2-(2-Hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole and Its O/"NH or S"-Substituted Derivatives J. Phys. Chem. A 2007, 111, 6354-6360
32. Liang, F.; Wang, L.; Ma, D.; Jing, X.; Wang, F. Oxadiazole-Containing Material with Intense Blue Phosphorescence Emission for Organic Light-Emitting Diodes Appl. Phys. Lett. 2002, 81, 4-6
33. Tamoto, N.; Adachi, C.; Nagai, K. Electroluminescence of 1,3,4-Oxadiazole and Triphenylamine-Containing Molecules as an Emitter in Organic Multilayer Light Emitting Diodes Chem. Mater. 1997, 9, 1077-1085
34. Uchida, M.; Adachi, C.; Koyama, T.; Taniguchi, Y. Charge Carrier Trapping Effect by Luminescent Dopant Molecules in Single-Layer Organic Light Emitting Diodes J. Appl. Phys. 1999, 86, 1680-1687
35. Wang, J. F.; Jabbour, G. E.; Mash, E. A.; Anderson, J.; Zhang, Y.; Lee, P. A.; Armstrong, N. R.; Peyghambarian, N.; Kippelen, B. Oxadiazole Metal Complex for Organic Light-Emitting Diodes Adv. Mater. 1999, 11, 1266-1269
36. Hu, Y.; Zhang, Y.; Liang, F.; Wang, L.; Ma, D.; Jing, X. Blue Organic Light-Emitting Diodes Based on an Oxadiazole-Containing Organic Molecule Exhibiting Excited State Intramolecular Proton Transfer Synth. Met. 2003, 137, 1123-1124
37. Blouin, N.; Michaud, A.; Leclerc, M. A Low-Bandgap Poly(2,7-carbazole) Derivative for Use in High-Performance Solar Cells Adv. Mater. 2007, 19, 2295-2300
38. Park, H. S.; Roy, A.; Beaupré, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Bulk Heterojunction Solar Cells with Internal Quantum Efficiency Approaching 100% Nat. Photonics 2009, 3, 297-302
39. Hou, J.; Chen, H.; Zhang, S.; Li, G.; Yang, Y. Synthesis, Characterization, and Photovoltaic Properties of a Low Band Gap Polymer Based on Silole-Containing Polythiophenes and 2,1,3-Benzothiadiazole J. Am. Chem. Soc. 2008, 130, 16144-16145
40. Qin, R.; Li, W.; Li, C.; Du, C.; Veit, C.; Schleiermacher, H.; Andersson, M.; Bo, Z.; Liu, Z.; Inganäs, O. A Planar Copolymer for High Efficiency Polymer Solar Cells J. Am. Chem. Soc. 2009, 131, 14612-14613
41. He, Y.; Zhao, G.; Min, J.; Zhang, M.; Li, Y. Poly(thienylene- benzothiadiazole-thienylene-vinylene): A Narrow Bandgap Polymer with Broad Absorption from Visible to Infrared Region Polymer 2009, 50, 5055-5058
42. Zhang, J.; Yang, Y.; He, C.; He, Y.; Zhao, G.; Li, Y. Solution-Processable Star-Shaped Photovoltaic Organic Molecule with Triphenylamine Core and Benzothiadiazole-Thiophene Arms Macromolecules 2009, 42, 7619-7622
43. Wienk, M. M.; Turbiez, M. G. R.; Struijk, M. P.; Fonrodona, M.; Janssen, R. A. J. Low-Band Gap Poly(di-2-thienylthienopyrazine): Fullerene Solar Cells Appl. Phys. Lett. 2006, 88, 153511-153513
44. He, Y.; Wu, W.; Zhao, G.; Liu, Y.; Li, Y. Poly(3,6-dihexyl-thieno[3,2-b] thiophene vinylene): Synthesis, Field-Effect Transistors, and Photovoltaic Properties Macromolecules. 2008, 41, 9760-9766
45. Liang, Y.; Wu, Y.; Feng, D.; Tsai, S.; Son, H.; Li, G.; Yu, L. Development of New Semiconducting Polymers for High Performance Solar Cells J. Am. Chem. Soc. 2009, 131, 56-57
46. Liang, Y.; Feng, D.; Wu, Y.; Tsai, S. T.; Li, G.; Ray, C.; Yu, L. Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties J. Am. Chem. Soc. 2009, 131, 7792-7799
47. 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 09; Gaussian, Inc.: Wallingford, CT, 2009.
48. Handy, N. C. The Molecular Physics Lecture 2004: (i) Density Functional Theory, (ii) Quantum Monte Carlo Mol. Phys. 2004, 102, 2399-2409
49. 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
50. 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
51. Hrobáriková, V.; Hrobárik, P.; Gajdoš, P.; Fitilis, I.; Fakis, M.; Persephonis, P.; Zahradník, P. Benzothiazole-Based Fluorophores of Donor-π-Acceptor-π-Donor Type Displaying High Two-Photon Absorption J. Org. Chem. 2010, 75, 3053-3068
52. Hrobárik, P.; Hrobáriková, V.; Sigmundová, I.; Zahradník, P.; Fakis, M.; Polyzos, I.; Persephonis, P. Benzothiazoles with Tunable Electron-Withdrawing Strength and Reverse Polarity: A Route to Triphenylamine-Based Chromophores with Enhanced Two-Photon Absorption J. Org. Chem. 2011, 76, 8726-8736
53. Hrobárik, P.; Sigmundová, I.; Zahradník, P.; Kasák, P.; Arion, V.; Franz, E.; Clays, K. Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses? J. Phys. Chem. C 2010, 114, 22289-22302
54. Kerkines, I. S. K.; Petsalakis, I. D.; Theodorakopoulos, G. Excited-State Intramolecular Proton Transfer in Hydroxyoxime-Based Chemical Sensors J. Phys. Chem. A 2011, 115, 834-840
55. Rostov, I. V.; Amos, R. D.; Kobayashi, R.; Scalmani, G.; Frisch, M. J. Studies of the Ground and Excited-State Surfaces of the Retinal Chromophore Using CAM-B3LYP J. Phys. Chem. B 2010, 114, 5547-5555
56. Liu, X.; Zhang, X.; Hou, Y.; Teng, F.; Lou, Z. Theoretical Investigation on Properties of the Ground and Lowest Excited States of a Red Emitter with Donor-π-Acceptor Structure Chem. Phys. 2011, 381, 100-104
57. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
58. Forés, M.; Duran, M.; SolaÌ€, M.; Adamowicz, L. Excited-State Intramolecular Proton Transfer and Rotamerism of 2-(2′-Hydroxyvinyl)benzimidazole and 2-(2′-Hydroxyphenyl)imidazole J. Phys. Chem. A 1999, 103, 4413-4420
59. Jin, R.; Zhang, J.; Hao, L. Theoretical Study of the Excited-State Intramolecular Proton Transfer and Rotamerism in 2,5-Bis(2-hydroxyphenyl)-1,3,4- oxadiazole Theor. Chem. Acc. 2010, 126, 351-360
60. Kasha, M.; Heldt, J.; Gormin, D. Triplet State Potentials in the Competitive Excitation Mechanisms of Intramolecular Proton Transfer J. Phys. Chem. 1995, 99, 7281-7284
61. Marcus, R. A. Electron Transfer Reactions in Chemistry. Theory and Experiment Rev. Mod. Phys. 1993, 65, 599-610
62. Marcus, R. A. Chemical and Electrochemical Electron-Transfer Theory Annu. Rev. Phys. Chem. 1964, 15, 155-196
63. Lemaur, V.; Steel, M.; Beljonne, D.; Brédas, J. L.; Cornil, J. Photoinduced Charge Generation and Recombination Dynamics in Model Donor/Acceptor Pairs for Organic Solar Cell Applications: A Full Quantum-Chemical Treatment J. Am. Chem. Soc. 2005, 127, 6077-6086
64. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. Hopping Transport in Conductive Heterocyclic Oligomers: Reorganization Energies and Substituent Effects J. Am. Chem. Soc. 2005, 127, 2339-2350
65. Cheung, D. L.; Troisi, A. Theoretical Study of the Organic Photovoltaic Electron Acceptor PCBM: Morphology, Electronic Structure, and Charge Localization J. Phys. Chem. C 2010, 114, 20479-20488
66. McMahon, D. P.; Trois, A. Evaluation of the External Reorganization Energy of Polyacenes J. Phys. Chem. Lett. 2010, 1, 941-946
67. Köse, M. E.; Long, H.; Kim, K.; Graf, P.; Ginley, D. Charge Transport Simulations in Conjugated Dendrimers J. Phys. Chem. A 2010, 114, 4388-4393
68. Sakanoue, K.; Motoda, M.; Sugimoto, M.; Sakaki, S. A Molecular Orbital Study on the Hole Transport Property of Organic Amine Compounds J. Phys. Chem. A 1999, 103, 5551-5556
69. Berlin, Y. A.; Hutchison, G. R.; Rempala, P.; Ratner, M. A.; Michl, J. Charge Hopping in Molecular Wires As a Sequence of Electron-Transfer Reactions J. Phys. Chem. A 2003, 107, 3970-3980
70. Lin, B. C.; Cheng, C. P.; You, Z. Q.; Hsu, C. P. Charge Transport Properties of Tris(8-hydroxyquinolinato)aluminum(III): Why It Is an Electron Transporter J. Am. Chem. Soc. 2005, 127, 66-67
71. Gruhn, N. E.; da Silva Filho, D. A.; Bill, T. G.; Malagoli, M.; Coropceanu, V.; Kahn, A.; Brédas, J. L. The Vibrational Reorganization Energy in Pentacene: Molecular Influences on Charge Transport J. Am. Chem. Soc. 2002, 124, 7918-7919
72. Pearson, R. G. Absolute Electronegativity and Absolute Hardness of Lewis Acids and Bases J. Am. Chem. Soc. 1985, 107, 6801-6806
73. Norton, J. E.; Brédas, J. L. Polarization Energies in Oligoacene Semiconductor Crystals J. Am. Chem. Soc. 2008, 130, 12377-12384
74. Delgado, M. C. R.; Pigg, K. R.; da Silva Filho, D. A.; Gruhn, N. E.; Sakamoto, Y.; Suzuki, T.; Osuna, R. M.; Casado, J.; Hernández, V.; Navarrete, J. T. L. Impact of Perfluorination on the Charge-Transport Parameters of Oligoacene Crystals J. Am. Chem. Soc. 2009, 131, 1502-1512
75. Irfan, A.; Zhang, J. P. Effect of One Ligand Substitution on Charge Transfer and Optical Properties in Mer -Alq3: A Theoretical Study Theor. Chem. Acc. 2009, 124, 339-344