Browse > Article
http://dx.doi.org/10.5764/TCF.2018.30.3.159

Synthesis of Blue-green Naphthoxy, Chloro Derivative Zinc-phthalocyanines with LCD Requirements  

Kumar, Rangaraju Satish (Department of Advanced Organic Materials Engineering,Chungnam National University)
Min, Kyeong Su (Department of Advanced Organic Materials Engineering,Chungnam National University)
Son, Young-A (Department of Advanced Organic Materials Engineering,Chungnam National University)
Publication Information
Textile Coloration and Finishing / v.30, no.3, 2018 , pp. 159-167 More about this Journal
Abstract
Here we designed and synthesized new zinc phthalocyanines and structures were fully confirmed by spectral and elemental analysis. All phthalocyanines have a very good solubility in industrial solvents like chloroform, dichloromethane, dimethyl sulfoxide, N,N-dimethyl formamide, propylene glycol monomethyl ether acetate (PGMEA), acetone, tetrahydrofuran and acetonitrile. UV-Visible absorption and transmittance in PGMEA showed that these dyes have suitable spectral properties for LCD color filters. By Triton X surfactant study, we confirmed that these dyes are not showing any aggregation in PGMEA. We dissolved the all phthalocyanines in LCD fabricating solvent (PGMEA), and all phthalocyanines showed more than 8 wt% of solubility. Finally, all of these results concluded that PCK1, PCK2 and PCK3 are fit for LCD green color filter.
Keywords
phthalocyanines; synthesis; Triton X; tetrachlorophthalonitrile; zinc;
Citations & Related Records
연도 인용수 순위
  • Reference
1 M. G. Iglesias, J. H. Yum, R. H. Baker, S. M. Zakeeruddin, P. Zechy, P. Vazquez, E. Palomares, M. Gratzel, M. K. Nazeeruddin, and T. Torres, Effect of Anchoring Groups in Zinc Phthalocyanine on the Dye-sensitized Solar Cell Performance and Stability, Chem. Sci., 2, 1145(2011).   DOI
2 D. Lin, Y. Wang, Q. Zhang, J. Zhou, L. Zhou, and S. Wei, The Substituted Amino Group Type Dependent Sensitivity Enhancing of Cationic Phthalocyanine Derivativesfor Photodynamic Activity, J. Photochem. Photobiol. A Chem., 315, 107(2016).   DOI
3 Y. Zorlu, F. Dumoulin, D. Bouchu, V. Ahsen, and D. Lafont, Monoglycoconjugated Water-Soluble Phthalocyanines, Design and Synthesis of Potential Selectively Targeting PDT Photosensitisers, Tetrahedron Lett., 51, 6615(2010).   DOI
4 P. Cook and H. Chambrier, "The Porphyrine Handbook, Edited by K. M. Kadish, R. Guilard, and K. M. Smith", Academic Press, Amsterdam, Vol. 19, pp.105-150, 2003.
5 J. Jeong, R. S. Kumar, N. Mergu, and Y. A. Son, Photophysical, Electrochemical, Thermal and Aggregation Properties of New Metal Phthalocyanines, J. Mol. Struct., 1147, 469(2017).   DOI
6 C. Kim, R. S. Kumar, N. Mergu, K. Jun, and Y. A. Son, Synthesis, Optical, Electrochemical and Theoretical Studies of New Multicyclic Substituted Phthalocyanines, J. Nanosci. Nanotechnol., 18, 3192(2017).
7 K. S. Ku, R. S. Kumar, and Y. A. Son, Synthesis, Spectral and Photophysical Properties of Anthracene Substituted Phthalocyanines; A Study as Polyurethane Electrospun Nanofibers, J. Nanosci. Nanotechnol., 18, 1716(2017).
8 J. Jeong, R. S. Kumar, I. J. Kim, and Y. A. Son, Synthesis,Characterization of Symmetrical and Unsymmetrical Naphthoxy Substituted Metallophthalocyanines, Mol. Cryst. Liq. Cryst., 644, 249(2017).   DOI
9 K. H. Bell and L. F. McCaffery, Regioselective Monomethylation of Unsymmetrical Naphthalenediols with Methanolic HCl, Aust. J. Chem., 46, 731(1993).   DOI
10 S. Xia, Z. Sun, L. Yi, and Y. Wang, Synthesis of Soluble Polyimide Derived from Novel Naphthalene Diamines for Liquid Crystal Alignment Layers and a Preliminary Study on the Mechanism of Imidization, RSC Adv., 3, 14661(2013).   DOI
11 H. Karacaa, B. Cayegil, and S. Sezer, Synthesis Characterization and Metal Sensing Applications of Novel Chalcone Substituted Phthalocyanines, Synth. Met., 215, 134(2016).   DOI
12 T. V. Basova, N. S. Mikhaleva, A. K. Hassan, and V. G. Kiselev, Thin Films of Fluorinated 3d-Metal Phthalocyanines as Chemical Sensors of Ammonia: An Optical Spectroscopy Study, Sens. Actuators B, 227, 634(2016).   DOI
13 S. Lee and S. K. Obendorf, Use of Electrospun Nanofiber Web for Protective Textile Materials as Barriers to Liquid Penetration, Text. Res. J., 77, 696(2007).   DOI
14 S.R. Forrest, Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques, Chem. Rev., 97, 1793(1997).   DOI
15 C. C. Leznoff and A. B. P. Lever, "Phthalocyanines Properties and Applications", Vol. 2, VCH Publisher, New York, 1993.
16 F. Yang and S. R. Forrest, Photocurrent Generation in Nanostructured Organic Solar Cells, ACS Nano, 2, 1022(2008).   DOI
17 A. B. P. Lever and C. C. Leznoff, "Phthalocyanines: Properties and Applications", WileyVCH, Weinheim, 1989, 1993, 1996.
18 N.B. McKeown, "Phthalocyanine Materials: Synthesis, Structure and Function", Cambridge University Press, Cambridge, 1998.
19 Z. F. Huang, H. W. Bao, Y. Y. Yao, W. Y. Lu, and W. X. Chen, Novel Green Processes and Mechanism of Peroxymonosulfate Based on Supported Cobalt Phthalocyanine, Catalyst, Appl. Catal. B, 154, 36(2014).
20 I. Koc, M. VOzer, A.R. VOzkaya, and V. O. Bekaroglu, Electrocatalytic Activity, Methanol Tolerance and Stability of Perfluoroalkyl-Substituted Mononuclear, and Ball-Type DinuclearCobalt Phthalocyaninesfor Oxygen Reduction in Acidic Medium, Dalton Trans., 32, 6368(2009).
21 J. March, "Advanced Organic Chemistry Reactions, Mechanisms and Structure", 3ed., Wiley, New York, pp.853-933, 1985.
22 M. Durmus, M. M. Ayhan, A. G. Gurek, and V. Ahsen, Synthesis, Characterization and Electrochemical Properties of Tetra 7-Oxy-3-Biphenylcoumarin Substituted Metal-Free, Zinc(II),Cobalt(II) and Indium(III) Phthalocyanines, Dyes Pigm., 133, 311(2016).   DOI
23 P. Muthukumar, H. S. Kim, K. S. Ku,J. H. Park, and Y. A. Son, Synthesis,Characterization and Aggregation and Fluorescence Properties of Novel Highly Soluble Zinc Phthalocyanines Bearing Tetrakis-4-(3-(piperidin-1-yl)phenoxy) with Tetra and Dodecachloro Substituents, Fibers Polym., 17, 553(2016).   DOI
24 I. Ozcesmeci, Synthesis and Fluorescence Properties of Phthalocyanines with Dibromo- and Tribromo-phenoxy Functionalities, Synth. Met., 176, 128(2013).   DOI
25 J. Choi, S. H. Kim, W. Lee, C. Yoon, and J. P. Kim, Synthesis and Characterization of Thermally Stable Dyes with Improved Optical Properties for Dye-based LCD Color Filters, New J. Chem., 36, 812(2012).   DOI
26 M. Durmus and T. Nyokong, Synthesis and Solvent Effects on the Electronic Absorption and Fluorescence Spectral Properties of Substituted Zinc Phthalocyanines, Polyhedron, 26, 2767(2007).   DOI
27 N. Shinichi, Y. Hideo, Y. Tooru, Y. Yamada, and T. Assignee, Eur. Pat. Appl., 332409, 13 Sep 1989.