Textile Science and Engineering (한국섬유공학회지)

The Korean Fiber Society (한국섬유공학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Optical Characterization of a Zinc-phthalocyanine Derivative Exhibiting High Solubility in Nonpolar Solvents

비극성 용매에 높은 용해성을 가지는 프탈로시아닌 유도체 합성 및 광학 특성에 대한 연구

  • Hong, Sun-Mi (Department of Organic Material Science and Engineering, Pusan National University) ;
  • Mutyala, Anil Kumar (Department of Organic Material Science and Engineering, Pusan National University) ;
  • Park, Jong S. (Department of Organic Material Science and Engineering, Pusan National University)
  • Received : 2016.04.01
  • Accepted : 2016.07.02
  • Published : 2016.12.31
⟨ Previous Next ⟩

Abstract

Phthalocyanine (Pc) exhibits excellent thermal, chemical, and physical stability, as well as outstanding absorption and emission properties, which are useful for its application in the fields of color filters, chemosensors, and photosensitizers. However, unsubstituted Pc is insoluble in common organic solvents due to its inherent intermolecular aggregation behavior, and thus needs to be finely dispersed in the presence of dispersants before use. In this article, we present a new Pc derivative, prepared by attaching long aliphatic groups at peripheral positions of Pc, which shows high solubility in most nonpolar solvents, leading to good optical properties. For its synthesis, dodecanyl-zinc Pc (dodecanyl-Zn-Pc) was prepared via direct tetramerization, starting with 4-dodecanyl phthalonitrile as the intermediate. Various characterization techniques were employed to estimate the structural and optical features of dodecanyl-Zn-Pc, including $^1H$ nuclear magnetic resonance, matrix-assisted laser desorption/ionization, and ultraviolet-visual spectrophotometry and fluorimetry. In addition, the morphology of dodecanyl-Zn-Pc film was examined by polarized optical microscopy.

Keywords

References

  1. F. Ghani, J. Kristen, and H. Riegler, "Solubility Properties of Unsubstituted Metal Phthalocyanines in Different Types of Solvents", J. Chem. Eng. Data, 2012, 57, 439-449. https://doi.org/10.1021/je2010215
  2. A. Ogunsipe, D. Maree, and T. Nyokong, "Solvent Effects on the Photochemical and Fluorescence Properties of Zinc Phthalocyanine Derivatives", J. Mol. Struct., 2003, 650, 131-140. https://doi.org/10.1016/S0022-2860(03)00155-8
  3. J. S. Louis, D. Lehmann, M. Friedrich, and D. R. T. Zahn, "Study of Dependence of Molecular Orientation and Optical Properties of Zinc Phthalocyanine Grown under Two Different Pressure Conditions", J. Appl. Phys., 2007, 101, 013503. https://doi.org/10.1063/1.2403845
  4. N. Rapulenyane, E. Antunes, N. Masilela, and T. Nyokong, "Synthesis and Photophysicochemical Properties of Novel Zinc Phthalocyanines Mono Substituted with Carboxyl Containing Functional Groups", J. Photoch. Photobio. A., 2012, 250, 18-24. https://doi.org/10.1016/j.jphotochem.2012.09.007
  5. V. T. Verdree, S. Pakhomov, G. Su, M. W. Allen, A. C. Countryman, R. P. Hammer, and S. A. Soper, "Water Soluble Metallo-Phthalocyanines: The Role of the Functional Groups on the Spectral and Photophysical Properties", J. Fluoresc., 2007, 17, 547-563. https://doi.org/10.1007/s10895-007-0210-4
  6. N. He, Y. Chen, J. Bai, J. Wang, W. J. Blau, and J. Zhu, "Preparation and Optical Limiting Properties of Multiwalled Carbon Nanotubes with ${\pi}$-Conjugated Metal-Free Phthalocyanine Moieties", J. Phys. Chem. C., 2009, 113, 13029-13035.
  7. K. Sakamoto and E. Ohno-Okumura, "Syntheses and Functional Properties of Phthalocyanines", Materials, 2009, 2, 1127-1179. https://doi.org/10.3390/ma2031127
  8. A. Staicu, A. Pascu, A. Nuta, A. Sorescu, V. Raditoiu, and M. L. Pascu, "Studies about Phthalocyanine Photosensitizers to be Used in Photodynamic Therapy", Rom. Rep. Phys., 2013, 65, 1032-1051.
  9. J. Montanari, A. P. Perez, F. Di Salvo, V. Diz, R. Barnadas, L. Dicelio, F. Doctorovich, M. J. Morilla, and E. L. Romeroa, "Photodynamic Ultradeformable Liposomes: Design and Characterization", Int. J. Pharm., 2007, 330, 183-194. https://doi.org/10.1016/j.ijpharm.2006.11.015
  10. M. Durmus and T. Nyokong, "Photophysicochemical and Fluorescence Quenching Studies of Benzyloxyphenoxy Substituted Zinc Phthalocyanines", Spectrochim. Acta. A, 2008, 69, 1170-1177. https://doi.org/10.1016/j.saa.2007.06.029
  11. M. S. An, S. W. Kim, and J.-D. Hong, "Synthesis and Characterization of Peripherally Ferrocene-modified Zinc Phthalocyanine for Dye-sensitized Solar Cell", Bull. Korean Chem. Soc., 2010, 31, 3272-3278. https://doi.org/10.5012/bkcs.2010.31.11.3272
  12. S. Senthilarasu, R. Sathyamoorthy, and S. K. Kulkarni, "Substrate Temperature Effects on Structural Orientations and Optical Properties of ZincPthalocyanine (ZnPc) Thin Films", Mat. Sci. Eng. B-Solid., 2005, 112, 100-105.
  13. S. Dong, H. Tian, D. Song, Z. Yang, D. Yan, Y. Geng, and F. Wang, "The First Liquid Crystalline Phthalocyanine Derivative Capable of Edge-on Alignment for Solution Processed Organic Thin-film Transistors", Chem. Commun., 2009, 21, 3086-3088.
  14. Y. Zhou, T. Taima, T. Miyadera, T. Yamanari, and Y. Yoshida, "Structural Modifications of Zinc Phthalocyanine Thin Films for Organic Photovoltaic Applications", J. Appl. Phys., 2012, 111, 103117. https://doi.org/10.1063/1.4721409