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

다국어 초록 (Multilingual 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.

참고문헌 (Reference)

1 Forrest, S. R., "Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques" 97 : 1793-1896, 1997

2 Basova, T. V., "Thin Films of Fluorinated 3d-Metal Phthalocyanines as Chemical Sensors of Ammonia: An Optical Spectroscopy Study" 227 : 634-642, 2016

3 Delman, A. D., "Thermal Analysis" 539-, 1969

4 Lin, D., "The Substituted Amino Group Type Dependent Sensitivity Enhancing of Cationic Phthalocyanine Derivatives for Photodynamic Activity" 315 : 107-120, 2016

5 Cook, P., "The Porphyrine Handbook, Vol. 19" Academic Press 105-150, 2003

6 Ku, K. -S., "Synthesis, Spectral and Photophysical Properties of Anthracene Substituted Phthalocyanines;A Study as Polyurethane Electrospun Nanofibers" 18 : 1716-1722, 2017

7 Jeong, J., "Synthesis, Characterization of Symmetrical and Unsymmetrical Naphthoxy Substituted Metallophthalocyanines" 644 : 249-256, 2017

8 Güzel, E., "Synthesis, Characterization and Photodynamic Activity of a New Amphiphilic Zinc Phthalocyanine" 97 : 238-243, 2013

9 Durmus, M., "Synthesis, Characterization and Electrochemical Properties of Tetra 7-Oxy-3-Biphenylcoumarin Substituted Metal-Free, Zinc(II), Cobalt(II) and Indium(III) Phthalocyanines" 133 : 311-323, 2016

10 Muthukumar, P., "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" 17 : 553-559, 2016

11 Durmus, M., "Synthesis and Solvent Effects on the Electronic Absorption and Fluorescence Spectral Properties of Substituted Zinc Phthalocyanines" 26 : 2767-2776, 2007

12 Ng, A. C., "Synthesis and Photophysical Properties of Nonaggregated Phthalocyanines Bearing Dendritic Substituents" 32 : 5292-5298, 1999

13 Dieter, W., "Synthesis and Photochemical Properties of Phthalocyanine Zinc(II) Complexes Containing o-Carborane Units" 747 : 98-105, 2013

14 Gursel, Y. H., "Synthesis and Liquid Crystal Properties of Phthalocyanine Bearing a Star Polytetrahydrofuran Moiety" 28 : 1490-1496, 2009

15 Choi, J., "Synthesis and Characterization of Thermally Stable Dyes with Improved Optical Properties for Dye-Based LCD Color Filters" 36 : 812-818, 2012

16 Karacaa, H., "Synthesis Characterization and Metal Sensing Applications of Novel Chalcone Substituted Phthalocyanines" 215 : 134-141, 2016

17 Spadavecchia, J., "Spin-coated Thin Films of Metal Porphyrin–Phthalocyanine Blend for an Optochemical Sensor of Alcohol Vapours" 100 : 88-93, 2004

18 Ragoussi, M. -E., "Recent Advances in Phthalocyanine-Based Sensitizers for Dye-Sensitized Solar Cells" 29 : 6475-6489, 2013

19 Waltera, M. G., "Porphyrins and Phthalocyanines in Solar Photovoltaic Cells" 14 : 759-792, 2010

20 Leznoff, C. C., "Phthalocyanines: Properties and Applications, vol. 1, vol. 4" VCH 1996

21 Leznoff, C. C., "Phthalocyanines: Properties and Applications" VCH 1993

22 Rosa, M. C. D., "Photosensitized Singlet Oxygen and its Applications" 233 : 351-371, 2002

23 Jeong, J., "Photophysical, Electrochemical, Thermal and Aggregation Properties of New Metal Phthalocyanines" 1147 : 469-479, 2017

24 Cook, M. J., "Octa-alkoxy Phthalocyanine and Naphthalocyanine Derivatives: Dyes with Q-band Absorption in the Far Red or Near Infrared" 1 : 2453-2458, 1988

25 Zhu, B., "Novel Planar Binuclear Zinc Phthalocyanine Sensitizer for Dye-sensitized Solar Cells: Synthesis and Spectral, Electrochemical, and Photovoltaic Properties" 1079 : 61-66, 2015

26 Makhseed, S., "New Highly Soluble Phenoxy-Substituted Phthalocyanine and Azaphthalocyanine Derivatives: Synthesis, Photochemical and Photophysical Studies and a Typical Aggregation Behavior" 95 : 351-357, 2012

27 Zorlu, Y., "Monoglycoconjugated Water-Soluble Phthalocyanines. Design and Synthesis of Potential Selectively Targeting PDT Photosensitisers" 51 : 6615-6618, 2010

28 Elemans, J. A. A. W., "Molecular Materials by Self-Assembly of Porphyrins, Phthalocyanine, and Perylenes" 18 : 1251-1266, 2006

29 Zagal, J. H., "Metallophthalocyanines as Catalysts in Electrochemical Reactions" 119 : 89-136, 1992

30 Sytnyk, M., "Hydrogen-Bonded Organic Semiconductor Micro- And Nanocrystals: From Colloidal Syntheses to (Opto-)Electronic Devices" 136 : 16522-16532, 2014

31 Giribabu, L., "Highly Efficient Microwave-Assisted Synthesis of Subphthalocyanines" 37 : 4141-4147, 2007

32 Hoon, Y., "High Transmissional Green Dye for LCD And Synthetic Method Thereof"

33 García-Iglesias, M., "Effect of Anchoring Groups in Zinc Phthalocyanine on the Dye-Sensitized Solar Cell Performance and Stability" 2 : 1145-1150, 2011

34 March, J., "Advanced Organic Chemistry, Reactions, Mechanisms and Structure" Wiley 853-933, 1985