Browse > Article
http://dx.doi.org/10.9713/kcer.2018.56.6.792

Synthesis, Photophysical and Aggregation Properties of Novel Phenanthrene and Pyrene Substituted Phthalocyanines  

Kumar, Rangaraju Satish (Department of Advanced Organic Materials Engineering, Chungnam National University)
Son, Young-A (Department of Advanced Organic Materials Engineering, Chungnam National University)
Publication Information
Korean Chemical Engineering Research / v.56, no.6, 2018 , pp. 792-797 More about this Journal
Abstract
We have explained the synthesis of novel phenanthrene and pyrene substituted phthalocyanines (PC-PHE and PC-PYR) and fully confirmed the structures by its spectral, photo physical and elemental analysis. For these phthalocyanines we checked the UV-Visible absorbance in PGMEA and chloroform and transmittance checked in PGMEA. The transmittance results suggested that these phthalocyanines are showing more than 90% transmittance at the 450-550 nm region. These synthesized molecules are nicely soluble in almost all industrial solvents. We checked the aggregation property of these phthalocyanines in PGMEA, and the results suggested no any aggregation for these molecules in PGMEA. The thermogravimetric analysis results concluded that PC-PHE and PC-PYR had high thermal stability. All studies explain that these new phthalocyanines are more suitable for LCD green color filter application.
Keywords
Phenanthrene; Aggregation; LCD; Tetrachlorophthalonitrile; PGMEA;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Zhu, B., Zhang, X., Han, M., Deng, P. and Li, Q., "Novel Planar Binuclear Zinc Phthalocyanine Sensitizer for Dye-sensitized Solar Cells: Synthesis and Spectral, Electrochemical, and Photovoltaic Properties," J. Mol. Struct., 1079, 61-66(2015).   DOI
2 Waltera, M. G., Rudineb, A. B. and Wamser, C. C., "Porphyrins and Phthalocyanines in Solar Photovoltaic Cells," J. Porphyrins Phthalocyanines, 14, 759-792(2010).   DOI
3 Gursel, Y. H., Senkal, B. F., Kandaz, M. and Yakuphanoglu F., "Synthesis and Liquid Crystal Properties of Phthalocyanine Bearing a Star Polytetrahydrofuran Moiety," Polyhedron, 28, 1490-1496(2009).   DOI
4 Karacaa, H., Çayegil, B. and Sezer, S., "Synthesis Characterization and Metal Sensing Applications of Novel Chalcone Substituted Phthalocyanines," Synth. Met., 215, 134-141(2016).   DOI
5 Basova, T. V., Mikhaleva, N. S., Hassan, A. K. and Kiselev V. G., "Thin Films of Fluorinated 3d-Metal Phthalocyanines as Chemical Sensors of Ammonia: An Optical Spectroscopy Study," Sens. Actuators B, 227, 634-642(2016).   DOI
6 Lin, D., Wang, Y., Zhang, Q., Zhou, J., Zhou, L. and Wei S., "The Substituted Amino Group Type Dependent Sensitivity Enhancing of Cationic Phthalocyanine Derivatives for Photodynamic Activity," J. Photochem. Photobiol. A Chem., 315, 107-120(2016).   DOI
7 Zorlu, Y., Dumoulin, F., Bouchu, D., Ahsen, V. and Lafont, D., "Monoglycoconjugated Water-Soluble Phthalocyanines. Design and Synthesis of Potential Selectively Targeting PDT Photosensitisers," Tetrahedron Lett., 51, 6615-6618(2010).   DOI
8 Spadavecchia, J., Ciccarella, G., Siciliano, P., Capone, S. and Rella R., "Spin-coated Thin Films of Metal Porphyrin-Phthalocyanine Blend for an Optochemical Sensor of Alcohol Vapours," Sens. Actuators B, 100, 88-93(2004).   DOI
9 Elemans, J. A. A. W., Hameren, W. R. V., Nolte, R. J. M. and Rowan, A. E. "Molecular Materials by Self-Assembly of Porphyrins, Phthalocyanine, and Perylenes," Adv. Mater., 18, 1251-1266(2006).   DOI
10 Cook, P. and Chambrier, H., "The Porphyrine Handbook," edited by Kadish, K. M., Guilard, R. and Smith, K. M., Academic Press, Amsterdam (2003), Vol. 19, pp. 105-150.
11 Forrest, S. R., "Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques," Chem. Rev., 97, 1793-1896(1997).   DOI
12 Dieter, W., Tsaryova, O., Semioshkin, A., Gabel, D. and Suvorova, O., "Synthesis and Photochemical Properties of Phthalocyanine Zinc(II) Complexes Containing o-Carborane Units," J. Organomet. Chem., 747, 98-105(2013).   DOI
13 Leznoff, C. C. and Lever, A. B. P., Phthalocyanines: Properties and Applications, vol. 1. VCH: NewYork; 1996, vol. 4.
14 Guzel, E., Atsay, A., Nalbantoglu, N. S., Dogan, L., Gul, A. and Kocak, M. B. "Synthesis, Characterization and Photodynamic Activity of a New Amphiphilic Zinc Phthalocyanine," Dyes Pigm., 97, 238-243(2013).   DOI
15 Cook, M. J., Dunn, A. J., Howe, S. D., Thomson, A. J. and Harrison, K. J. "Octa-alkoxy Phthalocyanine and Naphthalocyanine Derivatives: Dyes with Q-band Absorption in the Far Red or Near Infrared," J. Chem. Soc. Perkin Trans., 1, 2453-2458(1988).
16 Makhseed, S., Tuhl, A., Samuel, J., Zimcik, P., Awadi, N. A. and Novakova, V., "New Highly Soluble Phenoxy-Substituted Phthalocyanine and Azaphthalocyanine Derivatives: Synthesis, Photochemical and Photophysical Studies and a Typical Aggregation Behavior," Dyes Pigm., 95, 351-357(2012).   DOI
17 Ragoussi, M.-E., Ince, M. and Torres, T. "Recent Advances in Phthalocyanine-Based Sensitizers for Dye-Sensitized Solar Cells," Eur. J. Org. Chem., 29, 6475-6489(2013).
18 Jeong, J., Kumar, R. S., Mergu, N. and Son, Y.-A., "Photophysical, Electrochemical, Thermal and Aggregation Properties of New Metal Phthalocyanines," J. Mol. Struct., 1147, 469-479(2017).   DOI
19 Ku, K.-S., Kumar, R. S. and Son, Y.A., "Synthesis, Spectral and Photophysical Properties of Anthracene Substituted Phthalocyanines; A Study as Polyurethane Electrospun Nanofibers," J. Nanosci. Nanotechnol., 18, 1716-1722(2017).
20 Jeong, J., Kumar, R. S., Kim, I. J. and Son, Y.-A., "Synthesis, Characterization of Symmetrical and Unsymmetrical Naphthoxy Substituted Metallophthalocyanines," Mol. Cryst. Liq. Cryst., 644, 249-256(2017).   DOI
21 March, J., "Advanced Organic Chemistry, Reactions, Mechanisms and Structure," 3rd ed., Wiley, New York, pp. 853-933(1985).
22 Garcia-Iglesias, M., Yum, J.-H., Humphry-Baker, R., Zakeeruddin, S. M., Zechy, P., Vazquez, P., Palomares, E., Gratzel, M., Nazeeruddin, M. K. and Torres, T., "Effect of Anchoring Groups in Zinc Phthalocyanine on the Dye-Sensitized Solar Cell Performance and Stability," Chem. Sci., 2, 1145-1150(2011).   DOI
23 Muthukumar, P., Kim, H.-S., Ku, K.-S., Park, J. H. and Son, Y.-A., "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, 553-559(2016).   DOI
24 Durmus, M., Ayhan, M. M., Gurek, A. G. and Ahsen, V., "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, 311-323(2016).   DOI
25 Giribabu, L., Vijay Kumar, C. H., Surendar, A., Reddy, V. G., Chandrasekharam, M. and Reddy P. Y., "Highly Efficient Microwave-Assisted Synthesis of Subphthalocyanines," Synth. Commun., 37, 4141-4147(2007).   DOI
26 Hoon, Y., Chul, K. J., Gun, L. B., Sanghun, A., Pil, H. J., Hun, K. S., Choi, K. J. and Namgoong, J. W., "High Transmissional Green Dye for LCD And Synthetic Method Thereof," US20140114077A1 patent.
27 Choi, J., Kim, S. H., Lee, W., Yoon, C. and Kim, J. P., "Synthesis and Characterization of Thermally Stable Dyes with Improved Optical Properties for Dye-Based LCD Color Filters," New J. Chem., 36, 812-818(2012).   DOI
28 Delman, A. D., Kelly, J. J., Stein, A. A. and Simms, F. B., "Thermal Analysis, In: Proceedings of the International Conference," 2nd ed., 1 New York: Academic Press; p. 539(1969).
29 Sytnyk, M., Glowacki, E. D., Yakunin, S., Voss, G., Scholfberger, W., Kriegner, D., Stangl, J., Trotta, R., Gollner, C., Tollabimazraehno, S., Romanazzi, G., Bozkurt, Z., Havlicek, M., Serdar Sariciftci, N. and Heiss, W., "Hydrogen-Bonded Organic Semiconductor Micro- And Nanocrystals: From Colloidal Syntheses to (Opto-)Electronic Devices," J. Am. Chem. Soc., 136, 16522-16532(2014).   DOI
30 Durmus, M. and Nyokong, T., "Synthesis and Solvent Effects on the Electronic Absorption and Fluorescence Spectral Properties of Substituted Zinc Phthalocyanines, " Polyhedron, 26, 2767-2776 (2007).   DOI
31 Ng, A. C., Li, X. Y. and Ng, D. K., "Synthesis and Photophysical Properties of Nonaggregated Phthalocyanines Bearing Dendritic Substituents," Macromolecules 32, 5292-5298(1999).   DOI
32 Leznoff, C. C. and Lever, A. B. P., "Phthalocyanines: Properties and Applications," VCH, New York, NY, USA, 1993.
33 Zagal, J. H., "Metallophthalocyanines as Catalysts in Electrochemical Reactions," Coord. Chem. Rev., 119, 89-136(1992).   DOI
34 Rosa, M. C. D. and Crutchley, R. J., "Photosensitized Singlet Oxygen and its Applications," Coord. Chem. Rev., 233, 351-371(2002).