Journal of Sensor Science and Technology (센서학회지)

The Korean Sensors Society (한국센서학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Characterization of 2, 6-Di-(4'-Methyl Phenyl) Pyrylium Fluoroborate and Perchlorate in Single Step Salts Using 4'-Methyl Acetophenone

  • Wie, Jin-Hyeong (Department of Energy and Environmental System Engineering, University of Seoul) ;
  • Hong, Young-Min (Department of Energy and Environmental System Engineering, University of Seoul) ;
  • Kim, Hyun-Ook (Department of Energy and Environmental System Engineering, University of Seoul) ;
  • Kim, Kyung-Hoon (Department of Chemical Engineering, University of Seoul) ;
  • Cho, Sung-Il (Department of Chemical Engineering, University of Seoul)
  • Received : 2011.11.29
  • Accepted : 2012.01.04
  • Published : 2012.01.24
Download PDF
⟨ Previous Next ⟩

Abstract

Due to its high conductivity, pyrylium has been frequently used in electron transfer reactions or in the synthesis of various organic materials. It has also been used as a sensor material. Traditionally, the compounds have been synthesized using various methods; mostly in a multiple steps. In this study, two pyrylium salts, 2, 6-di-(4'-methylphenyl) pyrylium fluoroborate and perchlorate were synthesized. The synthesis of these products was confirmed by 1H-NMR, LC/TOF-MS and FT-IR analyses while their photo-properties were analyzed using UV/VIS spectrophotometry. In addition, the electron transfer capacities of the salts were analyzed with a conductivity meter, it was found that their electron conductivities were high. When the synthesized compounds were dissolved in acetone, a green fluorescent material was observed to form. The fluorescent material can be used as a sensitizer in the electrical industry.

Keywords

References

  1. A. T. Balaban, G. W. Fischer, A. Dinulescu, A. V. Koblik, G. N. Dorofeenko, V. V. Mezheritski, and W. Schroth, Editors, Pyrylium salts: Synthesis, Reaction and Physical Properties, Advanced in Heterocyclic Chemistry, Suppl. II, Academic Press, New York, 1982.
  2. T. H. Steinberg, L. J. Jones, R. P. Haugland, and V. L. Singer, "SYPRO orange and SYPRO, red protein gel stains: one-step fluorescent staining of denaturing gels for detection of nanogram levels of protein", Anal. Biochem., vol. 239, no.2, pp. 223-237, 1996. https://doi.org/10.1006/abio.1996.0319
  3. G. Purvinis, P. S. Priambodo, M. Pomerantz, M. Zhou, T. A. Mal-donado, and R. Magnusson, "Secondharmonic generation in resonant waveguide gratings incorporating ionic self-assembled monolayer polymer Films", Opt. Lett., vol. 29, no. 10, pp. 1108-1110, 2004. https://doi.org/10.1364/OL.29.001108
  4. I. Polyzos, G. Tsigaridas, M. Fakis, V. Giannetas, P. Persephonis, and J. Mikroyannidis, "Substituent effect on the photobleaching of pyrylium salts under ultrashort pulsed illumination", J. Phys. Chem., vol. B 110, pp. 2593-2597, 2006.
  5. K. Binnemans, "Ionic liquid crystals", Chem. Rev., vol.105, pp. 4148-4204, 2005. https://doi.org/10.1021/cr0400919
  6. M. Fakis, J. Polyzos, G. Tsigaridas, J. Parthenios, A. Fragos, V. Giannetas, P. Persephonis, and J. Mikroyannidis, "Novel class of pyrylium dyes with high efficiency in lasing and two photon absorption fluorescence", Chem. Phys. Lett., vol. 323, no. 1, pp. 111-116, 2000. https://doi.org/10.1016/S0009-2614(00)00494-2
  7. D. Egan, M. Salmain, P. McArdle, G. Jaouen, and B. Caro, "FT-IR observation of covalent labelling of lysozyme crystals by organometallic complexes of transition metals", Spectrochim. Acta., vol. Part A 58, pp. 941-951, 2003.
  8. A. Diaspro and M. Robell, "Two-photon excitation of fluorescence for three-dimensional optical imaging of biological structures", J. Photochem Photobiol., vol B: Biol. 55, pp. 1-8, 2000.
  9. J. D. Tovar and T. M. Swager, "Pyrylium salts via electrophilic cyclization: applications for novel 3-arylisoquinoline syntheses", J. Org. Chem., vol. 64, pp. 6499-6504, 1999. https://doi.org/10.1021/jo990810x
  10. F. A. Scaramuzzo, A. Gonzalez-Campo, C. C. Wu, A. H. Velders, V. Subramaniam, G. Doddi, P. Mencarelli, M. Barteri, P. Jonkheijm, and J. Huskens, "Pyrylium monolayers as amino-reactive platform", Chem. Commun., vol. 46, no. 23, pp. 4193-4195, 2010. https://doi.org/10.1039/c002203a
  11. A. R. Katritzky, G. P. Savage, M. Pilarska, and Z. D. Szafran, "The synthesis and response to vapor challenges of new microsensor coatings pyridinium and pyrylim salts", Chem. Scr., vol. 29, pp. 235-239, 1989.
  12. M. R. Ganjali, M. Ghorbani, A. Daftari, P. Norouzi, H. Pirelahi, and H. D. Dargahani, "Highly selective liquid membrane sensor based on 1,3,5-triphenylpyrylium perchlorate for quick monitoring of sulfate ions", Bull. Korean Chem Soc., vol. 25, no. 2, pp.172-176, 2004. https://doi.org/10.5012/bkcs.2004.25.2.172
  13. B. G. Acosta, M. Comes, J. L. Bricks, M. A. Kudinova, V. V. Kurdyukov, A. I. Tolmachev, A. B. Descalzo, M. D. Marcos, R. M. Manez, A. Moreno, F. Sancenon, J. Soto, L. A. Villaescusa, K. Rurack, J. M. Barat, I. Escriche, and P. Amoros, "Sensory hybrid host materials for the selective chromo-fluorogenic detection of biogenic amines", Chem. Commun., vol. 21, pp. 2239-2241, 2006.
  14. G. J. Mohr, "Covalent bond formation as an analytical tool to optically detect neutral and anionic analytes", J. snb., vol. 107, pp. 2-13, 2005.
  15. N. Manoj, G. Ajayakumar, K. R. Gopidas, and C. H. Suresh, "Structure-absorption spectra correlation in a series of 2,6-dimethyl-4-arylpyrylium salts", J. Phys. Chem., vol. A 110, no. 39, pp. 11338-11345, 2006.
  16. C. H. Chen, J. J. Doney, and G. A. Reynolds, "Synthesis and reactions of 2,6-diphenyl 4-(trimethylsilyl)-4H-thiopyran", J. Org. Chem., vol. 47, no. 4, pp. 680-684, 1982. https://doi.org/10.1021/jo00343a015
  17. G. N. Dorofeenko and L. V. Dulenko, "A new method for the construction of pyrylium and pyridine rings fused to derivatives of furan and indole", Chem. Heterocycl. Compd., vol. 5, no. 3, pp. 417-421, 1969.
  18. W. Schroth, R. Spitzner, and E. Kleinpeter, "2,4,6 -tris (dialkylamino) pyrylium salts and related systems, synthesis and reaction behavior", Tetrahedron Lett., vol. 29, pp.4695-4698, 1988. https://doi.org/10.1016/S0040-4039(00)80583-3
  19. S. V. Krivun, A. I. Buryak, and S. N. Baranov, "Pyrylium salts from pyrones and some organometallic compounds", Chem. Heterocycl. Compd., vol. 9, no.10, pp.1191-1194, 1973. https://doi.org/10.1007/BF00477445
  20. T. S. Balaban and A. T. Balaban, Science of Synthesis; Houben-Weyl Methods of Molecular Transformations, Georg Thieme Verlag, Stuttgart, 2003.
  21. C. Mahler, U. Muller, W. Muller, V. Enkelmann, C. Moon, G. Brunklaus, H. Zimmermann, and S. Hoger, "Synthesis of highly phenylene substituted pphenylene oligomers from pyrylium salts", Chem. Commun., vol. 39, pp. 4816-4818, 2008.
  22. I. A. Levitsky, K. Kishikawa, S. H. Eichhorn, and T. M. Swager, "Exciton coupling and dipolar correlations in a columnar liquid crystal: photophysics of a bentrod hexacatenar mesogen", J. Am. Chem. Soc., vol. 122, no. 11, pp. 2474-2479, 2000. https://doi.org/10.1021/ja993947d
  23. S. E. Okan, D. C. Champenev, and J. Solut, "Molar conductance of aqueous solutions of sodium, potassium, and nickel trifluoro-methane sulfonate at $25{^{\circ}C}$", Chem., vol. 26, pp. 405-414, 1997.
  24. R. E. Johnson, Solute and Cathode Investigations in Propylene Glycol Sulfite, Lewis Research Center, Langley, 1967.