1,5-diaryl-3-benzimidazolyl-2-pyrazolines and pyrazoles – novel fluorescent dyes of pyrazoline family
Abstract
A series of novel aryl derivatives of 2-pyrazoline bearing 2-benzimidazolyl moiety was synthesized via condensation of corresponding chalcones with phenyl hydrazine. Pyrazoles on their background were obtained by the optimized oxidation procedure with manganese dioxide in benzene. Fluorescent characteristics of the title compounds were determined for their solutions in acetonitrile. Quantum-chemical modeling of molecular structure, UV/Vis spectra, electron density redistribution and structural relaxation at electronic excitation resulting in high fluorescence Stokes shifts were conducted as well.
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Wiley R. H., Jarboe C. H., Hayes F. N., Hansbury E., Nielsen J. T., Callahan P. X., Sellbrs M. C. 1,3,5-triaryl-2-pyrazolines for use as scintillation solutes // Journal of Organic Chemistry. - 1958. - V. 23. - P. 732-738.
Rivett D. E., Rosevear J., Wilshir J. F. K. The preparation and spectral properties of some monosubstituted 1,3,5-triphenyl-2-pyrazolines // Australian Journal of Chemistry -1979. - V. 32. - P. 1601-1612.
Wagner A., Schellhammer C.-W., Petersen S. Aryl-Δ2-pyrazolines as Optical Brighteners // Angewandte Chemie International Edition in English. - 1966. - V. 5, № 8. - P. 699-704.
Dorlars A., Schellhammer C.-W., Schroeder J. Heterocycles as Structural Units in New Opti-cal Brighteners // Angewandte Chemie International Edition in English. - 1975. - V. 14, № 10. - P. 665-679.
Sandler S. R., Tsou K. C. Fluorescence Spectral Study of Wavelength Shifters for Scintillation Plastics // The Journal of Chemical Physics. - 1963. - V. 39, № 4. - P. 1062-1067.
Bliznyuk V. N., Seliman A. F., Ishchenko A. A., Derevyanko N. A., DeVol T. A. New Effi-cient Organic Scintillators Derived from Pyrazoline // ACS Applied Materials & Interfaces. - 2016. - V. 8, № 20. - P. 12843-12851.
Gao X.-C., Cao H., Zhang L.-Q., Zhang B.-W., Cao Y., Huang C.-H. Properties of a new pyrazoline derivative and its application in electroluminescence // Journal of Materials Chem-istry. - 1999. - V. 9, № 5. - P. 1077-1080.
Sano T., Nishio Y., Hamada Y., Takahashi H., Usuki T., Shibata K. Design of conjugated mo-lecular materials for optoelectronics // Journal of Materials Chemistry. - 2000. - V. 10, № 1. - P. 157-161.
Peng Q., Lu Z.-Y., Huang Y., Xie M.-G., Xiao D., Han S.-H., Peng J.-B., Cao Y. Novel effi-cient green electroluminescent conjugated polymers based on fluorene and triarylpyrazoline for light-emitting diodes // Journal of Materials Chemistry. - 2004. - V. 14, № 3. - P. 396-401.
Ferle A., Pizzuti L., Inglez S. D., Caires A. R. L., Lang E. S., Back D. F., Flores A. F. C., Júnior A. M., Deflon V. M., Casagrande G. A. The first gold(I) complexes based on thiocar-bamoyl-pyrazoline ligands: Synthesis, structural characterization and photophysical properties // Polyhedron. - 2013. - V. 63. - P. 9-14.
Wang S.-Q., Liu S.-Y., Wang H.-Y., Zheng X.-X., Yuan X., Liu Y.-Z., Miao J.-Y., Zhao B.-X. Novel Pyrazoline-Based Selective Fluorescent Sensor for Hg2+ // Journal of Fluo-rescence. - 2014. - V. 24, № 3. - P. 657-663.
Hu S., Song J., Wu G., Cheng C., Gao Q. A new pyrazoline-based fluorescent sensor for Al3+ in aqueous solution // Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. - 2015. - V. 136, Part B. - P. 1188-1194.
Subashini G., Shankar R., Arasakumar T., Mohan P. S. Quinoline appended pyrazoline based Ni sensor and its application towards live cell imaging and environmental monitoring // Sensors and Actuators B: Chemical. - 2017. - V. 243. - P. 549-556.
Bozkurt E., Gul H. I. A novel pyrazoline-based fluorometric “turn-off” sensing for Hg2+ // Sensors and Actuators B: Chemical. - 2018. - V. 255, № 1. - P. 814-825.
Fahrni C. J., Yang L., VanDerveer D. G. Tuning the Photoinduced Electron-Transfer Thermo-dynamics in 1,3,5-Triaryl-2-pyrazoline Fluorophores: X-ray Structures, Photophysical Charac-terization, Computational Analysis, and in Vivo Evaluation // Journal of the American Chemi-cal Society. - 2003. - V. 1254. - P. 3799-3812.
Rana D. K., Dhar S., Bhattacharya S. C. An intriguing pH-triggered FRET-based biosensor emission of a pyrazoline-doxorubicin couple and its application in living cells // Physical Chemistry Chemical Physics. - 2014. - V. 16, № 13. - P. 5933-5936.
Barceló-Oliver M., Terrón A., García-Raso A., Lah N., Turel I. Intermolecular C-H...π inter-actions in 1,5-diphenyl-3-(2-pyridyl)-2-pyrazoline // Acta Crystallographica Section C Crystal Structure Communications. - 2010. - V. 66, № 6. - P. o313-o316.
Fang Q., Yamamoto T. Preparation of a new polymer containing photoluminescent pyrazoline unit in the main chain // Journal of Polymer Science Part A: Polymer Chemistry. - 2004. - V. 42, № 11. - P. 2686-2697.
Kramarenko S. F., Tkachev V. A., Tolmachev A. V., Voronkina N. I., Afanasyeva M. A., Krainov I. P. New organic luminophores for Langmuir multistructures // Thin Solid Films. - 1992. - V. 210-211, № 1. - P. 224-227.
Shen F., Peng A., Chen Y., Dong Y., Jiang Z., Wang Y., Fu H., Yao J. Photoinduced Electron Transfer in Coaggregates of Dicyanonaphthalene and Pyrazoline // The Journal of Physical Chemistry A. - 2008. - V. 112, № 11. - P. 2206-2210.
Dai Y., Guo M., Peng J., Shen W., Li M., He R., Zhu C., Lin S. H. Noncovalent interaction and its influence on excited-state behavior: A theoretical study on the mixed coaggregates of dicyanonaphthalene and pyrazoline // Chemical Physics Letters. - 2013. - V. 556. - P. 230-236.
Samshuddin S., Narayana B., Sarojini B. K., Khan M. T. H., Yathirajan H. S., Raj C. G. D., Raghavendra R. Antimicrobial, analgesic, DPPH scavenging activities and molecular docking study of some 1,3,5-triaryl-2-pyrazolines // Medicinal Chemistry Research. - 2012. - V. 21, № 8. - P. 2012-2022.
Akranth M., Md. Rahmat A., Md. Tauquir A., Rikta S., Omprakash T., Mymoona A., Md S., Alam M. M. Pyrazolines: A Biological Review // Mini-Reviews in Medicinal Chemistry. - 2013. - V. 13, № 6. - P. 921-931.
Udachin Y. M., Chursinova L. V., Przheval'skii N. M., Grandberg I. I., Tokmakov G. P. Lu-minescence properties of arylpyrazoles // Izvestiya Timiryazevskoi Sel'skokhozyaistvennoi Akademii. - 1980. - V. 3. - P. 162-169.
Evans N. A. Dye-sensitized photooxidation of some substituted 1,3-Diphenyl-2-pyrazolines // Australian Journal of Chemistry. - 1975. - V. 28, № 2. - P. 433-437.
Zoorob H. H., Hammouda H. A., Ismail E. Study of the Reactivity of 2-Cinnamoylbenzimidazole towards Thiourea, Urea, Hydrazines and Hydroxylamine Hydro-chloride // Zeitschrift für Naturforschung B. - 1977. - V. 32, № 4. - P. 443-446.
Hozien Z. A. Synthesis of some new heterocyclic systems derived from 2-acetylbenzimidazole // Journal of Chemical Technology & Biotechnology. - 1993. - V. 57, № 4. - P. 335-341.
Bapna A., Ojha S., Talesara G. L. Facile synthesis of alkoxyphthalimide derivatized benzimi-dazole assembled pyrazoles, pyrimidines and isoxazoles, via common intermediate chalcone // Indian Journal of Chemistry. - 2008. - V. 47B, № 7. - P. 1096-1107.
Shaharyar M., Abdullah M. M., Bakht M. A., Majeed J. Pyrazoline bearing benzimidazoles: Search for anticancer agent // European Journal of Medicinal Chemistry, B: Organic Chemis-try Including Medicinal Chemistry. - 2010. - V. 45, № 1. - P. 114-119.
Rajora J., Yadav J., Kumar R., Srivastava Y. K. Microwave assisted transformation of ben-zimidazolyl chalcones into N1-substituted pyrazolines and evaluation of their antimicrobial activities // Indian Journal of Chemistry, B: Organic Chemistry Including Medicinal Chemis-try. - 2010. - V. 49B, № 7. - P. 989-993.
Xian Y.-f., Li D.-f., Wang Y.-m. Synthesis of New Blue Pyrazoline Fluorescent Compounds and Study of Infrared Spectroscopy // Spectroscopy and Spectral Analysis. - 2008. - V. 28, № 07. - P. 1617-1620.
Cao X. Q., Lin X. H., Zhu Y., Ge Y. Q., Wang J. W. The optical properties, synthesis and characterization of novel 5-aryl-3-benzimidazolyl-1-phenyl-pyrazoline derivatives // Spectro-chimica Acta Part A: Molecular and Biomolecular Spectroscopy. - 2012. - V. 98. - P. 76-80.
Han Z., Yan J., Tang H. Q., He Y., Zhu Y., Ge Y. Q. Novel simple fluorescent sensor for nickel ions // Tetrahedron Letters. - 2017. - V. 58, № 13. - P. 1254-1257.
Maiorova O. A., Egorova A. Y. Reaction of 3-arylhydrazono-3H-furan-2-ones with o-phenylenediamine // Russian Journal of Organic Chemistry. - 2013. - V. 49, № 9. - P. 1348-1351.
Azaheterocycles Based on a,ß-Unsaturated Carbonyls. / Chebanov V. A., Desenko S. M., Gur-ley T. W. - Berlin Heidelberg: Springer-Verlag Berlin Heidelberg, 2008. - 210 p.
M.T. Albuquerque H., M.M. Santos C., A.S. Cavaleiro J., M.S. Silva A. Chalcones as Versa-tile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles // Current Or-ganic Chemistry. - 2014. - V. 18, № 21. - P. 2750-2775.
Krasovitskii B. M., Pereyaslova D. G., Skripkina V. T., Yagupolskii L. M., Popov V. I. Or-ganic luminophores with fluorine-containing substituents // Dyes and Pigments. - 1988. - V. 9, № 1. - P. 21-35.
Doroshenko A. O., Skripkina V. T., Shershukov V. M., Ponomarev O. A. Fluorescence quenching of a 1,3,5-triaryl-2-pyrazoline derivatives with acceptor substituents in the 5-phenyl radical // Optics and Spectroscopy. - 1997. - V. 82, № 3. - P. 338-343.
Doroshenko A. O., Skripkina V. T., Schershukov V. M., Ponomaryov O. A. Fluorescence Quenching in Bichromophoric Systems with Nonconjugated Chromophores: 5-Substituted Derivatives of 1,3,5-Triaryl-2-Pyrazoline // Journal of Fluorescence. - 1997. - V. 7. - P. 131-138.
Dong B., Wang M., Xu C. Synthesis, photoluminescence properties and theoretical insights on 1,3-diphenyl-5-(9-anthryl)-2-pyrazoline and -1H-pyrazole // Luminescence. - 2013. - V. 28, № 5. - P. 628-633.
Pragst F., Jugelt W. Elektrochemisches Verhalten von N-Aryl-Δ2-pyrazolinen. VI. Kinetische Untersuchungen an der rotierenden Scheibenelektrode zum Mechanismus der anodischen Dimerisierung von 1,3,5-Triaryl-Δ2-pyrazolinen // Journal für Praktische Chemie. - 1974. - V. 316, № 6. - P. 981-998.
Melhuish W. H. Absolute spectrofluorometry // Journal of Research of the National Institute of Standards and Technology. Sec. A: Physical Chemistry. - 1972. - V. 76A, № 6. - P. 547-560.
Photoluminescence of solutions: with applications to photochemistry and analytical chemistry. / Parker C. A. - Amsterdam: Elsevier Publishing Company, 1968.
Kotelevskiy S. I. The true refractive index correction to the fluorescence intensity in the com-mercial fluorescence spectrophotometer // Journal of Luminescence. - 1998. - V. 79, № 3. - P. 211-214.
Becke A. D. Density functional thermochemistry. III. The role of exact exchange // The Journal of Chemical Physics. - 1993. - V. 98, № 7. - P. 5648-5652.
Woon D. E., Jr. T. H. D. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon // The Journal of Chemical Physics. - 1993. - V. 98, № 2. - P. 1358-1371.
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., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J., J.A. , Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J.,
Brothers E., Kudin K. N., Staroverov V. N., Keith T., Kobayashi R., Normand J., Raghava-chari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Strat-mann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J. Gaussian 09, Revision B.01 // Book Gaussian 09, Revision B.01 / Editor. - Wallingford CT: Gaussian, Inc., 2010.
Bylaska E. J., de Jong W. A., Govind N., Kowalski K., Straatsma T. P., Valiev M., Wang D., Apra E., Windus T. L., Hammond J., Nichols P., Hirata S., Hackler M. T., Zhao Y., Fan P.-D., Harrison R. J., Dupuis M., Smith D. M. A., Nieplocha J., Tipparaju V., Krishnan M., Wu Q., Van Voorhis T., Auer A. A., Nooijen M., Brown E., Cisneros G., Fann G. I., Fruchtl H., Garza J., Hirao K., Kendall R., Nichols J. A., Tsemekhman K., Wolinski K., Anchell ., Bernholdt D., Borowski P., Clark T., Clerc D., Dachsel H., Deegan M., Dyall K., Elwood D., Glen-dening E., Gutowski M., Hess A., Jaffe, Johnson B., Ju J., Kobayashi R., Kutteh R., Lin Z., Littlefield R., Long X., Meng B., Nakajima T., Niu S., Pollack L., Rosing M., Sandrone G., Stave M., Taylor H., Thomas G., van Lenthe J., Wong A., Zhang Z. NWChem, A Computa-tional Chemistry Package for Parallel Computers, Version 5.1 // Book NWChem, A Computa-tional Chemistry Package for Parallel Computers, Version 5.1 / EditorPacific Northwest Na-tional Laboratory, Richland, Washington, 99352-0999, USA, 2007.
Luzanov A. V., Zhikol O. A. Electron invariants and excited state structural analysis for elec-tronic transitions within CIS, RPA, and TDDFT models // International Journal of Quantum Chemistry. - 2009. - V. 110, № 4. - P. 902-924.
Luzanov A. V., Zhikol O. A. Excited State Structural Analysis: TDDFT and Related Models // Practical Aspects of Computational Chemistry I / Leszczynski J., Shukla M. K. - Dordrecht: Springer, 2011.
Steiner T., Desiraju G. R. Distinction between the weak hydrogen bond and the van der Waals interaction // Chemical Communications. - 1998.- № 8. - P. 891-892.
Steiner T. The Hydrogen Bond in the Solid State // Angewandte Chemie International Edition. - 2002. - V. 41. - P. 48-76.
Bader R. F. W. Atoms in molecules // Accounts of Chemical Research. - 1985. - V. 18, № 1. - P. 9-15.
Bader R. F. W. A quantum theory of molecular structure and its applications // Chemical Reviews. - 1991. - V. 91, № 5. - P. 893-928.
Luzanov A. V. The Structure of the Electronic Excitation of Molecules in Quantum-chemical Models // Russian Chemical Reviews. - 1980. - V. 49, № 11. - P. 1033-1048.
Doroshenko A. O., Kirichenko A. V., Mitina V. G., Ponomaryov O. A. Spectral properties and dynamics of the excited state structural relaxation of the ortho analogues of POPOP — Effec-tive abnormally large Stokes shift luminophores // Journal of Photochemistry and Photobiol-ogy A: Chemistry. - 1996. - V. 94, № 1. - P. 15-26.
Doroshenko A. O., Kyrychenko A. V., Baumer V. N., Verezubova A. A., Ptyagina L. M.
Molecular structure, fluorescent properties and dynamics of excited state structural relaxation of the oxadiazolic ortho-analog of POPOP with the additional sterical hindrance // Journal of Molecular Structure. - 2000. - V. 524, № 1–3. - P. 289-296.
Doroshenko A. O., Kyrychenko A. V., Waluk J. Low Temperature Spectra of the ortho-POPOP Molecule: Additional Arguments of Its Flattening in the Excited State // Journal of Fluorescence. - 2000. - V. 10, № 1. - P. 41-48.
Iliashenko R. Y., Borodin O. O., Wera M., Doroshenko A. O. 2,5-bis[2-(2-phenyl-1,3-oxazol-5-yl)phenyl]-1,3,4-oxadiazole – new sterically hindered high Stokes shift fluorophore sensi-tive to media viscosity // Journal of Photochemistry and Photobiology A: Chemistry. - 2015. - V. 298. - P. 68-77.
Wodrich M. D., Corminboeuf C., Schreiner P. R., Fokin A. A., Schleyer P. v. R. How Accu-rate Are DFT Treatments of Organic Energies? // Organic Letters. - 2007. - V. 9, № 10. - P. 1851-1854.
Jacquemin D., Wathelet V., Perpete E. A., Adamo C. Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules // Journal of Chemical Theory and Computation. - 2009. - V. 5. - P. 2420-2435.
Rurack K., Bricks J. L., Schulz B., Maus M., Reck G., Resch-Genger U. Substituted
,5-Diphenyl-3-benzothiazol-2-yl-Δ2-pyrazolines: Synthesis, X-ray Structure, Photophysics, and Cation Complexation Properties // The Journal of Physical Chemistry A. - 2000. - V. 104, № 26. - P. 6171-6188.
Rettig W. Charge Separation in Excited States of Decoupled Systems—TICT Compounds and Implications Regarding the Development of New Laser Dyes and the Primary Process of Vi-sion and Photosynthesis // Angewandte Chemie International Edition in English. - 1986. - V. 25, № 11. - P. 971-988.
Grabowski Z. R., Rotkiewicz K., Rettig W. Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures // Chemical Reviews. - 2003. - V. 103, № 10. - P. 3899-4032.
Doroshenko A. O., Pivovarenko V. G. Fluorescence quenching of the ketocyanine dyes in po-lar solvents: anti-TICT behavior // Journal of Photochemistry and Photobiology A: Chemistry. - 2003. - V. 156, № 1. - P. 55-64.
Doroshenko A. O., Bilokin M. D., Pivovarenko V. G. New fluorescent dye of dibenzalcy-clopentanone series possessing increased solvatochromism and “energy gap law” regulated fluorescence quenching in polar solvents // Journal of Photochemistry and Photobiology A: Chemistry. - 2004. - V. 163, № 1. - P. 95-102.
