Laboratory of heterocycles
Our research is focused on design, synthesis and study of heterocyclic compounds (namely benzothiazole derivatives) with nonlinear optical properties. The attraction of such type of compounds lies in their possible application in various fields of optoelectronics: modulation of laser light frequency, organic semiconductors, OLED-diodes, photodynamic anticancer therapy, etc.
The original methods of synthesis of new benzothiazole derivatives with dipolar, quadrupolar and octupolar symmetry have been developed. The prepared compounds showed an enhanced nonlinear optical response and high value of two photon absorption cross-section. The effective molecular structure is predicted on the base of quantum-chemical calculations. The special laser measurements of optoelectronic properties are realised in the collaboration with International Laser Center in Bratislava, University in Leuwen (Belgium) and University in Patras (Greece).
MEMBERS
Teachers and researchers
Prof. RNDr. Pavol Zahradník, DrSc. - Professor Emeritus
Doc. RNDr. Peter Magdolen, PhD.
PharmDr. Ivica Sigmundová, PhD.
Mgr. Andrea Martinická, PhD. (neé Fülöpová)
PhD. students
MSc. students
Bc. students
Dominika Žárska
Former members and collaborators
Mgr. Mária Michálková Nečedová, PhD.
Mgr. Alexandra Čibová, PhD.
Ing. Kristína Plevová, PhD.
RNDr. Dušan Loos, CSc.
Mgr. Veronika Hrobáriková, PhD.
Mgr. Peter Hrobárik, PhD.
Mgr. Marek Cigáň, PhD.
Mgr. Branislav Horváth, PhD.
RNDr. Peter Gajdoš, PhD.
PUBLICATIONS
Publications from 2000
45. Noskovičova, E., Lorenc, D., Magdolen, P., Sigmundová, I., Zahradník, P., Velič, D. Broadband two-photon absorption cross sections of benzothiazole derivatives and benzobisthiazolium salts (2018) Chemical Physics Letters, 700, pp. 22-26.
DOI: 10.1016/j.cplett.2018.03.075
44. Čibová, A., Martinická, A., Magdolen, P., Zahradník, P., Cigáň, M., Uherek, M., Chorvát, D. Dicationic and monocationic benzobisthiazolium salts as potential NLO chromophores (2018) Dyes and Pigments, 149, pp. 597-611.
DOI: 10.1016/j.dyepig.2017.11.015
43. Danko, M., Hrdlovič, P., Martinická, A., Benda, A., Cigáň, M. Spectral properties of ionic benzotristhiazole based donor-acceptor NLO-phores in polymer matrices and their one- and two-photon cellular imaging ability (2017) Photochemical and Photobiological Sciences, 16 (12), pp. 1832-1844.
DOI: 10.1039/c7pp00239d
42. Michálková Nečedová, M., Martinická, A., Magdolen, P., Novakova, V., Zahradník, P. Phthalocyanine-triphenylamine dyads: Synthesis, electrochemical, spectral and DFT study (2017) Dyes and Pigments, 141, pp. 448-456.
DOI: 10.1016/j.dyepig.2017.02.025
41. Nečedová, M.M., Magdolen, P., Fülöpová, A., Cigáň, M., Zahradník, P., Filo, J. Synthesis, electrochemical, spectral and DFT study of novel thiazole-annelated subphthalocyanines with inherent chirality (2016) Dyes and Pigments, 130, pp. 24-36.
DOI: 10.1016/j.dyepig.2016.03.001
40. Hricovíniová, Z., Hricovíni, M., Brezová, V., Magdolen, P. New series of N-aryl- and N-heteroaryl-d-glucuronamides as potential anticancer agents: Synthesis and spectroscopic analysis (2016) Tetrahedron Asymmetry, 27 (7-8), pp. 361-368.
DOI: 10.1016/j.tetasy.2016.02.015
39. Nečedová, M., Magdolen, P., Novakova, V., Cigáň, M., Vlčková, S., Zahradník, P., Fülöpová, A. Synthesis and Photophysical, Electrochemical and Theoretical Study of Thiazole-Annelated Phthalocyanines (2015) European Journal of Organic Chemistry, 2015 (32), pp. 7053-7068.
DOI: 10.1002/ejoc.201500785
38. Čibová, A., Magdolen, P., Fülöpová, A., Kožíšek, J., Cigáň, M., Zahradník, P. Push-pull molecular structures based on angular benzobisthiazolium acceptor: Synthesis, photophysical properties and theoretical studies (2015) Tetrahedron, 71 (2), pp. 315-323.
DOI: 10.1016/j.tet.2014.11.047
37. Fakis, M., Hrobárik, P., Yushchenko, O., Sigmundová, I., Koch, M., Rosspeintner, A., Stathatos, E., Vauthey, E. Excited state and injection dynamics of triphenylamine sensitizers containing a benzothiazole electron-accepting group on TiO2 and Al2O3 thin films (2014) Journal of Physical Chemistry C, 118 (49), pp. 28509-28519.
DOI: 10.1021/jp509971q
36. Fülöpová, A., Magdolen, P., Károlyiová, M., Sigmundová, I., Zahradník, P. Unsymmetrical benzotristhiazole: A new electron-withdrawing core for octupolar chromophores (2013) Journal of Heterocyclic Chemistry, 50 (3), pp. 563-567.
DOI: 10.1002/jhet.1530
35. Čibová, A., Magdolen, P., Fülöpová, A., Zahradník, P. Conjugated push-pull salts derived from linear benzobisthiazole: Preparation and optical properties (2013) Chemical Papers, 67 (1), pp. 110-116.
DOI: 10.2478/s11696-012-0251-2
34. Fülöpová, A., Magdolen, P., Sigmundová, I., Zahradník, P., Rakovský, E., Cigáň, M. Benzotristhiazole based chromophores for nonlinear optics (2012) Journal of Molecular Structure, 1027, pp. 70-80.
DOI: 10.1016/j.molstruc.2012.06.018
33. 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 (2011) Journal of Organic Chemistry, 76 (21), pp. 8726-8736.
DOI: 10.1021/jo201411t
32. Cigáň, M., Gáplovský, A., Sigmundová, I., Zahradník, P., Dědic, R., Hromadová, M. Photostability of D-π-A nonlinear optical chromophores containing a benzothiazolium acceptor (2011) Journal of Physical Organic Chemistry, 24 (6), pp. 450-459.
DOI: 10.1002/poc.1782
31. 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? (2010) Journal of Physical Chemistry C, 114 (50), pp. 22289-22302.
DOI: 10.1021/jp108623d
30. Cigáň, M., Gáplovský, A., Gajdoš, P., Magdolen, P., Zahradník, P., Vetríková, Z. Photophysical properties and photostability of novel benzothiazole-based D-π-A-π-D systems (2010) Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 77 (5), pp. 984-993.
DOI: 10.1016/j.saa.2010.08.035
29. Zahradník, P., Magdolen, P., Zahradník, P. Thiazolo[4,5-d]thiazole - A new domain for potential optoelectronic application (2010) Tetrahedron Letters, 51 (44), pp. 5819-5821.
DOI: 10.1016/j.tetlet.2010.08.110
28. Hrobáriková, V., Hrobárik, P., Gajdoŝ, P., Fitilis, I., Fakis, M., Persephonis, P., Zahradník, P. Benzothiazole-based fluorophores of donor-π-acceptor-π-donor type displaying high two-photon absorption (2010) Journal of Organic Chemistry, 75 (9), pp. 3053-3068.
DOI: 10.1021/jo100359q
27. Batova, M., Klobucnikova, V., Oblasova, Z., Gregan, J., Zahradnik, P., Hapala, I., Subik, J., Schüller, C. Chemogenomic and transcriptome analysis identifies mode of action of the chemosensitizing agent CTBT (7-chlorotetrazolo[5,1-c]benzo[1,2,4]triazine) (2010) BMC Genomics, 11 (1), art. no. 153.
DOI: 10.1186/1471-2164-11-153
26. Gajdoš, P., Magdolen, P., Zahradník, P., Foltínová, P. New conjugated benzothiazole-N-oxides: Synthesis and biological activity (2009) Molecules, 14 (12), pp. 5382-5388.
DOI: 10.3390/molecules14125382
25. Zajac, M., Hrobárik, P., Magdolen, P., Foltínová, P., Zahradník, P. Donor-π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity (2008) Tetrahedron, 64 (46), pp. 10605-10618.
DOI: 10.1016/j.tet.2008.08.064
24. Franz, E., Harper, E.C., Coe, B.J., Zahradnik, P., Clays, K., Asselberghs, I. Benzothiazoliums and pyridiniums for second-order nonlinear optics (2008) Proceedings of SPIE - The International Society for Optical Engineering, 6999, art. no. 699923.
DOI: 10.1117/12.781194
23. Sigmundová, I., Zahradník, P., Magdolen, P., Bujdáková, H. Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring (2008) Arkivoc, 2008 (8), pp. 183-192.
DOI: 10.3998/ark.5550190.0009.815
22. Hrobárik, P., Horváth, B., Sigmundovà, I., Zahradník, P., Malkina, O.L. The impact of the π-electron conjugation on 15N, 13C and 1H NMR chemical shifts in push-pull benzothiazolium salts. Experimental and theoretical study (2007) Magnetic Resonance in Chemistry, 45 (11), pp. 942-953.
DOI: 10.1002/mrc.2074
21. Benková, Z., Černušák, I., Zahradník, P. Electric properties of formaldehyde, thioformaldehyde, urea, formamide, and thioformamide - Post-HF and DFT study (2007) International Journal of Quantum Chemistry, 107 (11), pp. 2133-2152.
DOI: 10.1002/qua.21399
20. Sigmundová, I., Zahradník, P., Loos, D. Synthesis and study of novel benzothiazole derivatives with potential nonlinear optical properties (2007) Collection of Czechoslovak Chemical Communications, 72 (8), pp. 1069-1093.
DOI: 10.1135/cccc20071069
19. Benková, Z., Černušák, I., Zahradník, P. Basis set and electron correlation effects on static electric properties of 1,3-thiazoles and 1,3-benzothiazoles as potential fragments in push-pull NLO chromophores (2006) Molecular Physics, 104 (13-14), pp. 2011-2026.
DOI: 10.1080/00268970600652979
18. Benková, Z., Černušák, I., Zahradník, P. Theoretical study of static electric properties of benzothiazole containing push-pull systems as potential candidates for NLO materials (2006) Structural Chemistry, 17 (3), pp. 287-300.
DOI: 10.1007/s11224-006-9033-1
17. Šimonová, E., Henselová, M., Zahradnik, P. Benzothiazole derivatives substituted in position 2 as biologically active substances with plant growth regulation activity (2005) Plant, Soil and Environment, 51 (11), pp. 496-505.
DOI: 10.17221/3623-PSE
16. Kóňa, J., Zahradník, P., Kozmon, S., Fabian, W.M.F. Role of solvent effects on nucleophilic substitution of 4H-pyran-4-one and its 2,6-dimethyl derivative with hydroxide ion in aqueous solution: Ab initio and density functional theory studies on a supermolecular reaction model (2005) Journal of Molecular Structure: THEOCHEM, 728 (1-3), pp. 117-122.
DOI: 10.1016/j.theochem.2005.02.026
15. Hrobárik, P., Sigmundová, I., Zahradník, P. Preparation of novel push-pull benzothiazole derivatives with reverse polarity: Compounds with potential non-linear optic application (2005) Synthesis, (4), pp. 600-604.
DOI: 10.1055/s-2004-837309
14. Magdolen, P., Vasella, A. Monocyclic, substituted imidazoles as glycosidase inhibitors (2005) Helvetica Chimica Acta, 88 (9), pp. 2454-2469.
DOI: 10.1002/hlca.200590182
13. Hrobarik, P., Zahradnik, P., Fabian, W.M.F. Computational design of benzothiazole-derived push-pull dyes with high molecular quadratic hyperpolarizabilities (2004) Physical Chemistry Chemical Physics, 6 (3), pp. 495-502.
DOI: 10.1039/B314150K
12. Foltínová, P., Magdolen, P., Zahradník, P. Inhibition of UV-induced mutagenesis in Euglena gracilis by benzothiazole derivatives (2003) Pharmazie, 58 (5), pp. 360-361.
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11. Kóňa, J., Zahradník, P., Fabian, W.M.F. Ab initio and density functional theory studies on the mechanism of nucleophilic vinylic substitution of 4H-pyran-4-one and 2-methyl-4H-pyran-4-one with ammonia (2003) Theoretical Chemistry Accounts, 109 (4), pp. 176-181.
DOI: 10.1007/s00214-002-0406-2
10. Mečiarová, M., Toma, Š., Magdolen, P. On the 3-aminophenothiazine synthesis (2003) Synthetic Communications, 33 (17), pp. 3049-3054.
DOI: 10.1081/SCC-120022480
9. Mečiarová, M., Toma, S., Magdolen, P. Ultrasound effect on the aromatic nucleophilic substitution reactions on some haloarenes (2003) Ultrasonics Sonochemistry, 10 (4-5), pp. 265-270.
DOI: 10.1016/S1350-4177(02)00157-8
8. Buffa, R., Zahradník, P., Foltínová, P. Synthesis and QSAR studies of new conjugated benzothiazole derivatives (2002) Collection of Czechoslovak Chemical Communications, 67 (12), pp. 1820-1832.
DOI: 10.1135/cccc20021820
7. Gáplovský, A., Donovalová, J., Magdolen, P., Toma, Š., Zahradnı́k, P. Spectroscopic study of 2-[2-(4-cyclaminophenyl)ethen-1-yl] benzothiazoles and their n-allylbenzothiazolium bromides. solvent and substituent effects on their ultraviolet-visible and fluorescence spectra (2002) Spectrochimica Acta - Part A Molecular and Biomolecular Spectroscopy, 58 (2), pp. 363-371.
DOI: 10.1016/S1386-1425(01)00545-5
6. Zahradnik, P., Buffa, R. Synthesis and theoretical study of a new type of pentacyclic bis-benzothiazolium compound (2002) Molecules, 7 (7), pp. 534-539.
DOI: 10.3390/70700534
5. Buffa, R., Zahradnik, P., Foltínová, P. Computer aided benzothiazole derivatives. Synthesis, structure and biological study of new push-pull conjugated benzothiazolium salts (2001) Heterocyclic Communications, 7 (4), pp. 331-336.
DOI: 10.1515/HC.2001.7.4.331
4. Kóňa, J., Zahradník, P., Fabian, W.M.F. Nucleophilic substitution by a hydroxide ion at a vinylic carbon: Ab initio and density functional theory studies on methoxyethene, 3-methoxypropenal, 2,3-dihydro-4H-pyran-4-one, and 4H-pyran-4-one (2001) Journal of Organic Chemistry, 66 (15), pp. 4998-5007.
DOI: 10.1021/jo001222i
3. Magdolen, P., Mečiarová, M., Toma, S. Ultrasound effect on the synthesis of 4-alkyl-(aryl)aminobenzaldehydes (2001) Tetrahedron, 57 (22), pp. 4781-4785.
DOI: 10.1016/S0040-4020(01)00403-3
2. Magdolen, P., Zahradnik, P., Foltinova, P. Synthesis, antimicrobial testing and QSAR study of new 2-phenylethenylbenzothiazolium salts substituted by cyclic amines (2000) Pharmazie, 55 (11), pp. 803-810.
1. Magdolen, P., Zahradnik, P., Foltinova, P. Synthesis and antimicrobial activity of new 2-phenylethynylbenzothiazoles and related salts (2000) Arzneimittel-Forschung/Drug Research, 50 (11), pp. 1023-1027.
DOI: 10.1055/s-0031-1300327