DOI QR코드

DOI QR Code

A Synthesis and Characterization of Pt(II) Complexes with Bipyrimidin-based Back-bone System

비피리미딘계 배위자를 골격으로 하는 Pt(II)착체의 합성 및 특성

  • Son, Seokhwan (Department of Chemical Engineering, Sunchon National University) ;
  • Ahn, Hogeun (Department of Chemical Engineering, Sunchon National University) ;
  • Chung, Minchul (Department of Chemical Engineering, Sunchon National University)
  • 손석환 (순천대학교 공과대학 고분자.화학공학부) ;
  • 안호근 (순천대학교 공과대학 고분자.화학공학부) ;
  • 정민철 (순천대학교 공과대학 고분자.화학공학부)
  • Received : 2016.01.29
  • Accepted : 2016.04.14
  • Published : 2016.08.01

Abstract

In this study, new platinum complexes were synthesized utilizing the ligand of a 2,2'-bispyrimidine (bpim), 2,2'-bipyridine (bpy), 5,5'-dimethyl-2,2'-bipyridine (5,5-mebpy), 5'-bromo-2,2'-bipyridine (5-brbpy), 5,5'-dibromo-2,2'-bipyridine (5,5-brbpy), 4,4'-dimethyl-2,2'-bipyridine (4,4-mebpy), 4,4'-dihexyl-2,2'-Bipyridine (4,4-hebpy), 1,10'-Phenanthroline (phen), 3,4,7,8'-tetramethyl-1,10'-Phenanthroline (3,4,7,8-phen). In order to determine chemical structure of Synthesized platinum complexes, $^1H(^{13}C)$-NMR, UV-vis and FT-IR were used and optical physics and chemical properties were measured PL. In the case of platinum complexes, wavelength has been identified 356~421 nm. Quantum efficiency in DMSO solution was appeared 0.05~0.46.

본 연구에서는 2,2'-bispyrimidine (bpim), 2,2'-bipyridine (bpy), 5,5'-dimethyl-2,2'-bipyridine (5,5-mebpy), 5'-bromo-2,2'-bipyridine (5-brbpy), 5,5'-dibromo-2,2'-bipyridine (5,5-brbpy), 4,4'-dimethyl-2,2'-bipyridine (4,4-mebpy), 4,4'-dihexyl-2,2'-Bipyridine (4,4-hebpy), 1,10'-Phenanthroline (phen), 3,4,7,8'-tetramethyl-1,10'-Phenanthroline (3,4,7,8-phen)을 사용하여 단핵 Platinum착체를 합성하였다. 합성되어진 Platinum착체의 화학적 구조를 결정하기 위해서 $^1H(^{13}C)$-NMR, FT-IR을 사용하였으며, 광 물리학적 특성에 대한 측정은 UV-vis, PL을 통하여 측정하였다. 합성한 Platinum착체는 356 nm~421 nm영역에서 발광파장이 확인되었으며, DMSO용액에서 내부양자효율이 0.05~0.46으로 나타났다.

Keywords

References

  1. Harima, Y., Okazaki, H., Kunugi, Y., Yamashita, K., Ishii, H. and Seki, K., "Formation of Schottky Barriers at Interfaces Between Metals and Molecular Semiconductors of p and n Type Conductances," Appl. Phys. Lett., 69, 1059-1061(1996). https://doi.org/10.1063/1.116930
  2. Reimers, J. R., Lu, T. X., Crossley, M. J. and Hush, N. S., "Molecular Electronic Properties of Fused Rigid Porphyrin-oligomer Molecular Wires," Nanotechnology, 7, 424-429(1996). https://doi.org/10.1088/0957-4484/7/4/022
  3. Maree, C. H. M., Roosendaal, S. J., Savenije, T. J., Schropp, R. E. I., Schaafsma, T. J. and Habraken, F. H. P. M., "Photovoltaic Effects in Porphyrin Polymer Films and Heterojunctions," J. Appl. Phys., 80, 3381-3389(1996). https://doi.org/10.1063/1.363203
  4. Kido, J., Kimura. M. and Nagai, K., "Multilayer White Light-emitting Organic Electroluminescent Device," Science, 267, 1332-1334(1995). https://doi.org/10.1126/science.267.5202.1332
  5. Helfich, W. and Schneider, W. G., "Recombination Radiation in Anthracene Crystals," Phys. Re. Lett., 14, 229-232(1965). https://doi.org/10.1103/PhysRevLett.14.229
  6. Helfich, W. and Schneider, W. G., "Electrical Conduction and Low Voltage Blue Electroluminescence in Vacuum-deposited Organic Films," J. Chem. Phys., 44, 2902-2909(1966). https://doi.org/10.1063/1.1727152
  7. Tang, C. W., VanSlyke, S. A. and Chen, C. H., "Electroluminescence of Doped Organic Thin Films," J. Appl. Phys., 65, 3610-3616(1989). https://doi.org/10.1063/1.343409
  8. Burroughes, J. H., Bradly, D. D. C., Brown, A. R., Marks, R. N., Mackay, K., Friend, R. H., Burns, P. L. and Holmes, A. B., "Light-emitting Diodes Based on Conjugated Polymers," Nature 347, 539-541(1990). https://doi.org/10.1038/347539a0
  9. Yu, H. J., Chung, K. W., Chun, B. H. and Kim, S. H., "Study on Electroluminescence of the Phosphorescent Iridium(III) Complex Prepared by Ultrasonic Wave," Korean Chem. Eng. Res., 49(3), 325-329(2011). https://doi.org/10.9713/kcer.2011.49.3.325
  10. Sauvageot, E., Marion, R., Sguerrac, F., Grimault, A., Daniellou, R., Hamel, M., Gaillard, S. and Renaud, J. L., "Iridium(iii) Dipyridylamine Complexes: Synthesis, Characterization and Catalytic Activities in Photoredox Reactions," Org. Chem. Front., 1, 639-644(2014). https://doi.org/10.1039/c4qo00059e
  11. Pal, A. K., Ducharme, P. D. and Hanan, G. S., "Enhanced Stereoselectivity in a di-Ru(II) Complex of an Achiral Bis-bidentate Ligand," Chem. Commun., 50, 3303-3305(2014). https://doi.org/10.1039/c3cc47856d
  12. Nisic, F., Colombo, A., Dragonetti, C., Roberto, D., Valore, A., Malicka, J. M., Cocchi, M., Freemane, G. R. and Williams, J. A. G., "Platinum(ii) Complexes with Cyclometallated 5-${\pi}$-delocalizeddonor-1, 3-di (2-pyridyl) Benzene Ligands as Efficient Phosphors for NIR-OLEDs," J. Mater. Chem. C., 2, 1791-1800(2014). https://doi.org/10.1039/c3tc32086c
  13. Unger, Y., Meyer, D., Molt, O., Schildknecht, C., Munster, I., Wagenblast, G. and Strassner, T., "Green-Blue Emitters: NHC Based Cyclometalated [Pt(C^C*)(acac)] Complexes," Angew. Chem., Int. Ed., 49, 10214-10216(2010). https://doi.org/10.1002/anie.201001316
  14. Yang, X., Wang, Z., Madakuni, S., Li, J. and Jabbour, G. E., "Efficient Blue and White Emitting Electrophosphorescent Devices Based on Platinum(II)[1, 3 Difluoro 4, 6 di-(2-pyridinyl) benzene] Chloride," Adv. Mater., 20, 2405-2409(2008). https://doi.org/10.1002/adma.200702940
  15. Brooks, J., Babayan, Y., Lamansky, S., Djurovich, P. I., Tsyba, I., Bau, R. and Thompson, M. E., "Synthesis and Characterization of Phosphorescent Cyclometalated Platinum Complexes," Inorg. Chem., 41, 3055-3066(2002). https://doi.org/10.1021/ic0255508
  16. Cocchi, M., Kalinowski, J., Fattori, V., Williams, J. A. G. and Murphy, L., "Color-variable Highly Efficient Organic Electrophosphorescent Diodes Manipulating Molecular Exciton and Excimer Emissions," Appl. Phys. Lett., 94, 073309-073309-3(2009). https://doi.org/10.1063/1.3086900
  17. Schwab, P. F. H., Fleischer, F. and Mich, J., "Preparation of 5-brominated and 5, 5'-dibrominated 2, 2'-bipyridines and 2, 2'-bipyrimidines," J. Org. Chem., 67, 443-449(2002). https://doi.org/10.1021/jo010707j
  18. Brotschi, C., Mathis, G. and Leumann, C. J., "Bipyridyl and Biphenyl DNA: A Recognition Motif Based on Interstrand Aromatic Stacking," Chem Eur. J., 11, 1911-1923(2005). https://doi.org/10.1002/chem.200400858
  19. Armarego, W. L. F. and Perrin, D. D., "Purification of Laboratory Chemicals," Butterworth-Heinemann. (1995).
  20. Chung, M. C., Jo, W. K., Son, S. H., Kwak, C. H., Lee, J. H. and Ahn, H. G., "Synthesis and Characterization of the Monomeric Platinum(II) Complexes with 2, 2'-Bipyridine Back-Bone Ligand," Advanced Materials Research, 811, 554-556(2012).
  21. Jo, W. K., Kwak, C. H., Lee, J. H., Jung, S. C., Ahn, H. G. and Chung, M. C., "Synthesis and Characterization of Platinum (II) Complexes Containing Spiro System," J. Nanosci Nanotechnol, 13(6), 4350-4354(2013). https://doi.org/10.1166/jnn.2013.7030
  22. Zhou, M., Robertson, G. P. and Roovers, J., "Comparative Study of Ruthenium(II) Tris (bipyridine) Derivatives for Electrochemiluminescence Application," Inorganic Chemistry, 44, 8317-8325(2005). https://doi.org/10.1021/ic0510112
  23. Lowry, M. S., Hudson, W. R., Pascal, R. A. Jr, and Berhard, S., "Accelerated Luminophore Discovery Through Combinatorial Synthesis," J. Am. Chem. Soc., 126, 14129-14135(2004). https://doi.org/10.1021/ja047156+