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Preparation of Organic Zn-Phthalocyanine-Based Semiconducting Materials and Their Optical and Electrochemical Characterization

DOI: 10.1155/2013/321563

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Abstract:

In order to increase the species of organic semiconductors, new Zn-phthalocyanines-based organic materials were synthesized and characterized. The new compounds have been characterized by 1H and 13C using NMR, FTIR, and UV-Vis. The absorption, fluorescence, and electrochemical properties were also studied. Green photoluminescence was observed in dilute solutions. In solid thin films, π-π* interactions influenced the optical properties, and redshifted photoluminescence spectra were obtained; red emissions for ZnPAL (647?nm) and ZnPTr (655?nm) were found. By cyclic voltammetry, the electrochemical band gap was estimated to be 1.94 and 1.17?eV for ZnPAl and ZnPTr, respectively. Single-layer diode devices of an indium tin oxide/Zn-phthalocyanine/aluminum configuration were fabricated and showed relatively low turn-on voltages (3.3?V for ZnPAl and 3?V for ZnPTr). 1. Introduction Phthalocyanines and related macrocycles have drawn considerable attention as molecular materials that give rise to outstanding electronic and optical properties. These properties arise from their electronic delocalization and make these compounds applicable in different fields of materials science; they are particularly promising as building blocks in nanotechnology. Some of the potential uses for phthalocyanines include nonlinear optical materials [1], liquid crystals [2], Langmuir-Blodgett (LB) films [3], optical data storage (computer recordable DVDs) [4], as electrochromic substances [5], low dimensional metals [6], and gas sensors [7], as photosensitizers [8], in photoelectrochemical cells [9] and electrophotographic applications [10]. Substitution has a strong influence on the π-electron conjugation of the macromolecule, since it makes salvation easier [11]. In recent years reports predict that a suitable functionalization of the M(Pc) molecules permits realizing more charge transfer processes decreasing [12], thus, the difference between HOMO and LUMO orbital (gap energy). We described herein, the synthesis and characterization of novel Zn(II) phthalocyanine derivatives which contain a 1,2,3 triazole unit on each benzo group, and tetra-substituted alkynyl phthalocyanine was synthesis for comparison purpose. ZnPcs structures were characterized by Fourier Transform Infrared Spectrophotometry (FTIR); we studied their electrochemical, optical (by UV-Vis absorption and photoluminescence spectroscopy), and electrical properties. 2. Experimental 2.1. Materials and Measurement N,N′-dimethylformamide (DMF) were freshly used; alcohols and initiator products were purchased from Aldrich.

References

[1]  M. Casstevens, M. Samok, J. Pfleger, and P. N. Prasad, “Dynamics of third‐order nonlinear optical processes in Langmuir—Blodgett and evaporated films of phthalocyanines,” Journal of Chemical Physics, vol. 92, no. 3, article 2019, 6 pages, 1990.
[2]  J. F. van der Pol, E. Neeleman, J. W. Zwikker et al., “Homologous series of liquid-crystalline metal free and copper octa-n-alkoxyphthalocyanines,” Liquid Crystals, vol. 6, no. 5, pp. 577–592, 1989.
[3]  H. Schultz, H. Lehmann, M. Rein, and M. Hanack, “Phthalocyaninatometal and related complexes with special electrical and optical properties,” Structure and Bonding, vol. 74, pp. 41–146, 1991.
[4]  J. E. Kuder, “Organic active layer materials for optical recording,” Journal of Imaging Science, vol. 32, no. 2, pp. 51–56, 1988.
[5]  M. Riou and C. Clarisse, “The rare earth substitution effect on the electrochemistry of diphthalocyanine films in contact with an acidic aqueous medium,” Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, vol. 249, no. 1-2, pp. 181–190, 1988.
[6]  T. J. Marks, “Electrically conductive metallomacrocyclic assemblies,” Science, vol. 227, no. 4689, pp. 881–889, 1985.
[7]  R. A. Collins and K. A. Mohammed, “Gas sensitivity of some metal phthalocyanines,” Journal of Physics D: Applied Physics, vol. 21, article 154, 1988.
[8]  E. Lukyanets, “Phthalocyanines as photosensitizers in the photodynamic therapy of cancer,” Journal of Porphyrins and Phthalocyanines, vol. 3, no. 6, article 424, 1999.
[9]  T. J. Klofta, J. Danziger, P. Lee, J. Pankow, K. W. Nebesny, and N. R. Armstrong, “Photoelectrochemical and spectroscopic characterization of thin films of titanyl phthalocyanine: comparisons with vanadyl phthalocyanine,” Journal of Physical Chemistry, vol. 91, no. 22, pp. 5646–5651, 1987.
[10]  S. Takano, T. Enokida, A. Kakuta, and Y. Mori, “A new polymorph of metal-free phthalocyanine,” Chemistry Letters, vol. 13, no. 12, pp. 2037–2040, 1984.
[11]  T. Ceyhan, M. Y. Yüksek, H. G. Ya?l?o?lu et al., “Synthesis, characterization and nonlinear absorption of novel octakis-POSS substituted metallophthalocyanines and strong optical limiting property of CuPc,” Dalton Transactions, pp. 2407–2413, 2008.
[12]  R. S. Iglesias, M. Segala, M. Nicolau, and B. Cabezo, “Computational study of the geometry and electronic structure of triazolephthalocyanines,” Journal of Materials Chemistry, vol. 12, pp. 1256–1261, 2002.
[13]  R. Valentin, W. Luminipa, R. Alina, A. Petrea, A. Viorica, and A. Ana, “Synthesis and characterization of some phthalic acid derivatives precursors for phthalocyanine chromogens,” Revista de Chimie, vol. 9, p. 59, 2008.
[14]  J. S. Michael, [thesis of doctorate], Faculty of the Virginia Polytechnic Institute and State, Blacksburg, Va, USA, 2006.
[15]  T. F. Baumann, M. S. Nasir, J. W. Sibert et al., “solitaire-Porphyrazines: synthetic, structural, and spectroscopic investigation of complexes of the novel binucleating norphthalocyanine-2,3-dithiolato ligand,” Journal of the American Chemical Society, vol. 118, no. 43, pp. 10479–10486, 1996.
[16]  F. Hac?velio?lu, M. Durmus, S. Yesilot, A. G. Gürek, A. K?l??, and V. Ahsen, “Synthesis, electronic absorption and fluorescence spectral properties of phenoxycyclotriphosphazene-substituted phthalocyanines,” Dyes and Pigments, vol. 79, pp. 14–23, 2008.
[17]  G. K. Karaoglan, G. Gümrük?ü, A. Koca, A. Gül, and U. Avc?ata, “Synthesis and characterization of novel soluble phthalocyanines with fused conjugated unsaturated groups,” Dyes and Pigments, vol. 90, no. 1, pp. 11–20, 2011.
[18]  N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function, Cambridge University Press, Cambridge, UK, 1998.
[19]  M. J. Cook, A. J. Dunn, S. D. Howe, A. J. Thomson, and K. J. Harrison, “Octa-alkoxy phthalocyanine and naphthalocyanine derivatives: dyes with Q-band absorption in the far red or near infrared,” Journal of the Chemical Society, Perkin Transactions, vol. 1, no. 8, pp. 2453–2458, 1988.
[20]  K. Hiz, N. Jaballah, and M. Chamli, “Synthesis and characterization of new anthracene-based semi-conducting materials,” Journal of Materials Science, vol. 47, no. 23, pp. 8067–8075, 2012.
[21]  K. Yoshino, M. Hikida, K. Tatsuno, K. Kaneto, and Y. Inuishi, “Emission spectra of phthalocyanine crystals,” Journal of the Physical Society of Japan, vol. 34, no. 2, pp. 441–445, 1973.
[22]  Y. Arslanoglua, A. Kocab, and E. Hamuryudan, “Synthesis of novel unsymmetrical phthalocyanines substituted with crown ether and nitro groups,” Polyhedron, vol. 26, no. 1, pp. 891–896, 2007.
[23]  K. Wang, Q. Fu, J. Ma et al., “Synthesis and electrochemical properties of a series of novel tetra(4-benzoyl)phenoxyphthalocyanine derivatives,” Science China Chemistry, vol. 55, no. 9, pp. 1872–1880, 2012.
[24]  P. W. M. Blom and M. C. J. M. Vissenberg, “Charge transport in poly(p-phenylene vinylene) light-emitting diodes,” Materials Science and Engineering: R: Reports, vol. 27, no. 3-4, pp. 53–94, 2000.
[25]  K. Hiz, N. Jaballah, and M. Chamli, “Synthesis and characterization of new anthracene-based semiconducting polyethers,” Journal of Applied Polymer Science, vol. 119, no. 3, pp. 1443–1449, 2011.
[26]  H. Ndayikengurukiye, S. Jacobs, W. Tachelet et al., “Alkoxylated p-phenylenevinylene oligomers: synthesis and spectroscopic and electrochemical properties,” Tetrahedron, vol. 53, no. 40, pp. 13811–13828, 1997.

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