Optical behavior of substituted 4-(2′-hydroxyphenyl)imidazoles

Journal of Physical Chemistry B

Volumn 119, Issue 6, 2015, Pages 2507-2514

  Jezewski, Artur ^a   Hammann, Tommy ^a   Cywiński, Piotr J ^b   Gryko, Daniel T ^a,c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b FRAUNHOFER INSTITUTE FOR APPLIED POLYMER RESEARCH   (Germany)

^c WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BOND STRENGTH (CHEMICAL); DIHEDRAL ANGLE; EXCITED STATES; FLUORESCENCE; PLANTS (BOTANY); SOLVENTS;

DUAL FLUORESCENCE; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENCE QUANTUM YIELD; INTRA-MOLECULAR HYDROGEN BONDS; NON-POLAR SOLVENTS; PHOTOPHYSICAL INVESTIGATION; RADIATIONLESS DEACTIVATION; STRUCTURAL INVESTIGATION;

HYDROGEN BONDS;

EID: 84922813193     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp507992x     Document Type: Article

References (43)

1. Kwon, J. E.; Park, S. Y. Advanced Organic Optoelectronic Materials: Harnessing Excited-State Intramolecular Proton Transfer (ESIPT) Process Adv. Mater. 2011, 23, 3615-3642
2. Zhao, J.; Ji, S.; Chen, Y.; Guo, H.; Yang, P. Excited State Intramolecular Proton Transfer (ESIPT): From Principal Photophysics to the Development of New Chromophores and Applications in Fluorescent Molecular Probes and Luminescent Materials Phys. Chem. Chem. Phys. 2012, 14, 8803-8817
3. Xu, Y.; Pang, Y. Zinc Binding-Induced Near-IR Emission from Excited-State Intramolecular Proton Transfer of a Bis(benzoxazole) Derivative Chem. Commun. 2010, 46, 4070-4072
4. Rode, M. F.; Sobolewski, A. L. Effect of Chemical Substituents on the Energetical Landscape of a Molecular Photoswitch: An Ab Initio Study J. Phys. Chem. A 2010, 114, 11879-11889
5. Demchenko, A. P.; Tangb, K.-C.; Chou, P.-T. Excited-state Proton Coupled Charge Transfer Modulated by Molecular Structure and Media Polarization Chem. Soc. Rev. 2013, 42, 1379-1408
6. Park, S.; Kwon, J. E.; Kim, S. H.; Seo, J.; Chung, K.; Park, S.-Y.; Jang, D.-J.; Medina, B. M.; Gierschner, J.; Park, S.-Y. A White-Light-Emitting Molecule: Frustrated Energy Transfer between Constituent Emitting Centers J. Am. Chem. Soc. 2009, 131, 14043-14049
7. Higashi, M.; Saito, S. Direct Simulation of Excited-State Intramolecular Proton Transfer and Vibrational Coherence of 10-Hydroxybenzo[ h ]quinoline in Solution J. Phys. Chem. Lett. 2011, 2, 2366-2371
8. Laurent, A. D.; Adamo, C.; Jacquemin, D. Dye Chemistry with Time-Dependent Density Functional Theory Phys. Chem. Chem. Phys. 2014, 16, 14334-14356
9. Chou, P.-T.; Chen, Y.-C.; Yu, W.-S.; Chou, Y.-H.; Wei, C.-Y.; Cheng, Y.-M. Excited-State Intramolecular Proton Transfer in 10-Hydroxybenzo[ h ]quinoline J. Phys. Chem. A 2001, 105, 1731-1740
10. Chen, K.-Y.; Hsieh, C.-C.; Cheng, Y.-M.; Lai, C.-H.; Chou, P.-T. Extensive Spectral Tuning of the Proton Transfer Emission from 550 to 675 nm via a Rational Derivatization of 10-Hydroxybenzo[ h ]quinoline Chem. Commun. 2006, 4395-4397
11. Piechowska, J.; Huttunen, K.; Gryko, D. T.; Wróbel, Z.; Lemmetyinen, H.; Tkachenko, N. V. Excited State Intramolecular Proton Transfer in Electron-rich and Electron-poor Derivatives of 10-Hydroxybenzo[ h ]quinoline J. Phys. Chen. A 2012, 116, 9614-9620
12. Douhal, A.; Amat-Guerri, F.; Acuña, A. U. Photoinduced Intramolecular Proton Transfer and Charge Redistribution in Imidazopyridines J. Phys. Chem. 1995, 99, 76-80
13. Shigemitsu, Y.; Mutai, T.; Houjou, H.; Araki, K. Excited-State Intramolecular Proton Transfer (ESIPT) Emission of Hydroxyphenylimidazopyridine: Computational Study on Enhanced and Polymorph-Dependent Luminescence in the Solid State J. Phys. Chem. A 2012, 116, 12041-12048
14. Stasyuk, A. J.; Banasiewicz, M.; Cyrański, M. K.; Gryko, D. T. Imidazo[1,2- a ]pyridines Susceptible to Excited State Intramolecular Proton Transfer: One-Pot Synthesis via an Ortoleva-King Reaction J. Org. Chem. 2012, 77, 5552-5558
15. Wang, H.; Zhang, H.; Abou-Zied, O. K.; Yu, C.; Romesberg, F. E.; Glasbeek, M. Femtosecond Fluorescence Upconversion Studies of Excited-state Proton-transfer Dynamics in 2-(2′-Hydroxyphenyl)benzoxazole (HBO) in Liquid Solution and DNA Chem. Phys. Lett. 2003, 367, 599-608
16. Wu, Y.; Peng, X.; Fan, J.; Gao, S.; Tian, M.; Zhao, J.; Sun, S. Fluorescence Sensing of Anions Based on Inhibition of Excited-State Intramolecular Proton Transfer J. Org. Chem. 2007, 72, 62-70
17. 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
18. Patil, V. S.; Padalkar, V. S.; Tathe, A. B.; Gupta, V. D.; Sekar, N. Synthesis, Photo-physical and DFT Studies of ESIPT Inspired Novel 2-(2′,4′-Dihydroxyphenyl) Benzimidazole, Benzoxazole and Benzothiazole J. Fluoresc. 2013, 23, 1019-1029
19. Padalkar, V. S.; Ponnadurai, R.; Sekar, N. Excited-State Intramolecular Proton Transfer (ESIPT) Inspired Azole-Quinoline Based Fluorophores: Synthesis and Photophysical Properties Study J. Lumin. 2014, 15, 558-564
20. Nagaoka, S.-i.; Nagashima, U.; Ohta, N.; Fujita, M.; Takemura, T. Electronic-state Dependence of Intramolecular Proton Transfer of o -Hydroxybenzaldehyde J. Phys. Chem. 1988, 92, 166-171
21. Nagaoka, S.-i.; Teramae, H.; Nagashima, U. Computational Study of Excited-State Intramolecular-Proton-Transfer of o-Hydroxybenzaldehyde and Its Derivatives Bull. Chem. Soc. Jpn. 2009, 82, 570-573
22. McMorrow, D.; Kasha, M. Intramolecular Excited-state Proton Transfer in 3-Hydroxyflavone. Hydrogen-bonding Solvent Perturbations J. Phys. Chem. 1984, 88, 2235-2243
23. Svechkarev, D. A.; Karpushina, G. V.; Lukatskaya, L. L.; Doroshenko, A. O. 2-(Benzimidazol-2-yl)-3-hydroxychromone Derivatives: Spectroscopic Properties and a Possible Alternative Intramolecular Proton Phototransfer Cent. Eur. J. Chem. 2008, 6, 443-449
24. Padalkar, V. S.; Ponnadurai, R.; Sekar, N. A combined experimental and DFT-TDDFT study of the excited-state intramolecular proton transfer (ESIPT) of 2-(2′-hydroxyphenyl) imidazole derivatives J. Fluoresc. 2013, 23, 839-851
25. Park, S.; Kwon, J. E.; Park, S. Y. Strategic Emission Color Tuning of Highly Fluorescent Imidazole-based Excited-state Intramolecular Proton Transfer Molecules Phys. Chem. Chem. Phys. 2012, 14, 8878-8884
26. Skonieczny, K.; Ciuciu, A. I.; Nichols, E.; Hugues, V.; Blanchard-Desce, M.; Flamigni, L.; Gryko, D. T. Bright, emission tunable fluorescent dyes based on imidazole and π-expanded imidazole J. Mater. Chem. 2012, 22, 20649-20664
27. Shienok, A. I.; Koltsova, L. S.; Zaichenko, N. L.; Marevtsev, V. S. Excited-state intramolecular proton transfer in 2,4,5-triarylimidazole molecules Russ. Chem. Bull. Int. Ed. 2002, 51, 2050-2054
28. Ciuciu, A. I.; Skonieczny, K.; Koszelewski, D.; Gryko, D. T.; Flamigni, L. Dynamics of Intramolecular Excited State Proton Transfer in Emission Tunable, Highly Luminescent Imidazole Derivatives J. Phys. Chem. C 2013, 117, 791-803
29. Forés, M.; Duran, M.; Solá, 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
30. Park, S.; Kwon, O.-H.; Lee, Y.-S.; Jang, D.-J.; Park, S. Y. Imidazole-Based Excited-State Intramolecular Proton-Transfer (ESIPT) Materials: Observation of Thermally Activated Delayed Fluorescence (TDF) J. Phys. Chem. A 2007, 111, 9649-9653
31. Eseola, A. O.; Adepitan, O.; Goerls, H.; Plass, W. Electronic/Substituents Influence on Imidazole Ring Donor-Acceptor Capacities Using 1 H -Imidazo[4,5- f ][1,10]phenanthroline Frameworks New J. Chem. 2012, 36, 891-902
32. Seo, M.-S.; Lee, A.; Kim, H. 2,2′-Dihydroxybenzil: A Stereodynamic Probe for Primary Amines Controlled by Steric Strain Org. Lett. 2014, 16, 2950-2953
33. 1: Synthesis of 2-Arylcoumaranones and 2-Phenylbenzofuran Tetrahedron 1999, 55, 11537-11546
34. Grimmet, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: New York, 1984; Vol. 5, pp 457-507.
35. Wang, C.; Gao, Q.; Huang, J. A Novel pH-Sensitive Chiral Amphiphile: Synthesis, Aggregation, and Interaction with β-Cyclodextrin Langmuir 2003, 19, 3757-3761
36. Park, S.; Kwon, O.-H.; Kim, S.; Park, S.; Choi, M.-G.; Cha, M.; Park, S. Y.; Jang, D.-J. Imidazole-Based Excited-State Intramolecular Proton-Transfer Materials: Synthesis and Amplified Spontaneous Emission from a Large Single Crystal J. Am. Chem. Soc. 2005, 127, 10070-10074
37. Buttke, K.; Baumgartel, H.; Niclas, H.-J.; Schneider, M. Synthesis, Structure, and Photophysical Properties of Polyarylated Imidazoles and Oxazoles J. Prakt. Chem. 1997, 339, 721-728
38. Jayabharathi, J.; Thanikachalam, V.; Perumal, M. V.; Srinivasan, N. Synthesis, Crystal Structure, Kamlet-Taft and Catalan Solvatochromic Analysis of Novel Imidazole Derivatives J. Fluoresc. 2012, 22, 409-417
39. Zhang, Y.; Wang, J.-H.; Zheng, W.; Chen, T.; Tong, Q.-X.; Li, D. An ESIPT Fluorescent Dye Based on HBI with High Quantum Yield and Large Stokes Shift for Selective Detection of Cys J. Mater. Chem. B 2014, 2, 4159-4166
40. Shono, H.; Ohkawa, T.; Tomoda, H.; Mutai, T.; Araki, K. Fabrication of Colorless Organic Materials Exhibiting White Luminescence Using Normal and Excited-State Intramolecular Proton Transfer Processes ACS Appl. Mater. Interfaces 2011, 3, 654-657
41. Mutai, T.; Tomoda, H.; Ohkawa, T.; Yabe, Y.; Araki, K. Switching of Polymorph-Dependent ESIPT Luminescence of an Imidazo[1,2- a ]pyridine Derivative Angew. Chem., Int. Ed. 2008, 47, 9522-9524
42. Stasyuk, A. J.; Banasiewicz, M.; Ventura, B.; Cyrański, K. M.; Gryko, D. T. Benzo[ a ]imidazo[5,1,2- cd ]indolizines-New Class of Molecules Displaying Excited State Intramolecular Proton Transfer New J. Chem. 2014, 38, 189-197
43. Mutai, T.; Sawatani, H.; Shida, T.; Shono, H.; Araki, K. Tuning of Excited-State Intramolecular Proton Transfer (ESIPT) Fluorescence of Imidazo[1,2- a ]pyridine in Rigid Matrices by Substitution Effect J. Org. Chem. 2013, 78, 2482-2489