Optical and electrical properties of novel peripherally tetra and mono -quinoleinoxy substituted metallophtalocyanines

Two new Zinc phtalocyanine, ZnPcR1 and ZnPcR4, with peripheral mono and tetra quinoleinoxy substituents of the phtalocyanine ring, were characterized to investigate their optical and electrical properties. The modification of the chemical structure allows the elongation of the π-conjugation, leading to an enhanced solubility as well as a broadening of the ZnPcR1 and ZnPcR4 absorption spectra. The UV–Visible absorption spectra show a typical behavior of phtalocyanine for the two π-conjugated systems with an optical band gap of 1.70 and 1.74 eV for ZnPcR1 and ZnPcR4 respectively and the Photoluminescence study exhibits a green emission for both compounds. The highest occupied molecular orbital and lowest unoccupied molecular orbital levels were estimated using cyclic voltammetry analysis and the calculated electrochemical gap was found to be equal to the optical one. Current–voltage characteristics and impedance spectroscopy measurements performed on sandwich structures ITO/phtalocyanine derivatives/Al are used to elucidate the conduction mechanisms. The static electrical characterizations showed a space charge limited conduction with exponential trap distribution at high applied bias voltage. The impedance spectra were discussed in terms of an equivalent circuit model designed as a parallel resistor Rp and capacitor Cp network in series with a resistor Rs. The evolution of the electrical parameters deduced from fitting of the experimental data is discussed. The conduction mechanism revealed by I–V characteristics is in agreement with the impedance spectroscopy results.

[1]  G. Horowitz,et al.  Mobility in Polycrystalline Oligothiophene Field‐Effect Transistors Dependent on Grain Size , 2000 .

[2]  B. Korgel,et al.  Growth kinetics and metastability of monodisperse tetraoctylammonium bromide capped gold nanocrystals , 2004 .

[3]  L. Do,et al.  Impedance spectroscopy of single- and double-layer polymer light-emitting diode , 2000 .

[4]  F. Josse,et al.  Phthalocyanines as sensitive materials for chemical sensors , 1996 .

[5]  Charles E. Swenberg,et al.  Electronic Processes in Organic Crystals , 1982 .

[6]  A. Salimi,et al.  Highly sensitive amperometric sensor for micromolar detection of trichloroacetic acid based on multiwalled carbon nanotubes and Fe(II)-phtalocyanine modified glassy carbon electrode. , 2013, Materials science & engineering. C, Materials for biological applications.

[7]  H. P. Oliveira,et al.  Dielectric spectroscopy of blends of polyvinylalcohol and polypyrrole , 2003 .

[8]  M. Ferenets,et al.  Thin Solid Films , 2010 .

[9]  Yasin Arslanoğlu,et al.  Synthesis of novel unsymmetrical phthalocyanines substituted with crown ether and nitro groups , 2007 .

[10]  D. Fox Physics and Chemistry of the Organic Solid State , 1963 .

[11]  Wenjun Wu,et al.  Starburst triarylamine based dyes for efficient dye-sensitized solar cells. , 2008, The Journal of organic chemistry.

[12]  Yang Hou,et al.  Synthesis and electrochemical properties of a series of novel tetra(4-benzoyl)phenoxyphthalocyanine derivatives , 2012, Science China Chemistry.

[13]  Temperature dependent transport properties in molybdenum oxide doped α-NPD , 2010 .

[14]  T. Nyokong,et al.  Synthesis, electrochemical and photochemical properties of unsymmetrically substituted zinc phthalocyanine complexes , 2002 .

[15]  J. Simon,et al.  Annelides. 7. Discotic mesophases obtained from substituted metallophthalocyanines. Toward liquid crystalline one-dimensional conductors , 1982 .

[16]  M. Knupfer,et al.  Orientation and electronic properties of phthalocyanines on polycrystalline substrates , 2009 .

[17]  Tebello Nyokong,et al.  Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines , 2007 .

[18]  C. Brett,et al.  Direct electrochemical determination of carbaryl using a multi-walled carbon nanotube/cobalt phthalocyanine modified electrode. , 2009, Talanta.

[19]  H. Peisert,et al.  Site-Specific Charge-Transfer Screening at Organic/Metal Interfaces , 2009 .

[20]  Michael Hanack,et al.  The Effect of Structural Modifications on Charge Migration in Mesomorphic Phthalocyanines , 1994 .

[21]  A. Gül,et al.  A novel phthalocyanine conjugated with four salicylideneimino complexes: Photophysics and fluorescence quenching studies , 2012 .

[22]  N. Jaballah,et al.  Synthesis and characterization of new anthracene-based semi-conducting materials , 2012, Journal of Materials Science.

[23]  K. C. Kao,et al.  Electrical Transport in Solids , 1983 .

[24]  Henning Sirringhaus,et al.  Device Physics of Solution‐Processed Organic Field‐Effect Transistors , 2005 .

[25]  P. Balraju,et al.  Novel zinc porphyrin with phenylenevinylene meso-substituents: Synthesis and application in dye-sens , 2011 .

[26]  Hopping Models and ac Universality , 2001, cond-mat/0109254.

[27]  V. Singh,et al.  Schottky diode solar cells on electrodeposited copper phthalocyanine films , 2009 .

[28]  A. Jonscher,et al.  Electronic properties of amorphous dielectric films , 1967 .

[29]  S. Das,et al.  Studies on conduction mechanisms of pentacene based diodes using impedance spectroscopy , 2007 .

[30]  R. Silbey,et al.  Chain-length dependence of electronic and electrochemical properties of conjugated systems: polyacetylene, polyphenylene, polythiophene, and polypyrrole , 1983 .

[31]  Z. V. Vardeny,et al.  Electrically Symmetric Poly(Phenylene Acetylene) Diodes , 1994 .

[32]  M. Lampert,et al.  Current injection in solids , 1970 .

[33]  S. Al-Raqa The synthesis and photophysical properties of novel, symmetrical, hexadecasubstituted Zn phthalocyanines and related unsymmetrical derivatives , 2008 .

[34]  Jörg Fink,et al.  Fluorination of copper phthalocyanines: Electronic structure and interface properties , 2003 .

[35]  K. Hariharan,et al.  ac Conductivity analysis and dielectric relaxation behaviour of NaNO3–Al2O3 composites , 2005 .

[36]  T. Nyokong,et al.  Electrostatic self-assembly of quaternized 2,(3)-tetra(oxo-pyridine) phthalocyaninato chloroindium(III) with a series of tetrasulfonated phthalocyanines , 2009 .

[37]  Donal D. C. Bradley,et al.  Space-charge limited conduction with traps in poly(phenylene vinylene) light emitting diodes , 1997 .

[38]  T. Basova,et al.  Phthalocyanine films as active layers of optical sensors for pentachlorophenol detection , 2009 .

[39]  Richard A. Klenkler,et al.  Integration of an M-phthalocyanine layer into solution-processed organic photovoltaic cells for improved spectral coverage , 2011 .

[40]  H. Griesser,et al.  Highly resolved dual phosphorescence of xanthone in several hosts , 1981 .

[41]  C. Pearson,et al.  Application of impedance spectroscopy to the study of organic multilayer devices , 2000 .

[42]  Y. Gök,et al.  Synthesis and characterization of new metal-free and nickel(II) phthalocyanines containing hexaazadioxa macrobicyclic moieties , 2008 .

[43]  R. Chaâbane,et al.  Investigation of the electrical properties of the metal-calixarene-semiconductor structures , 1997 .

[44]  Christoph Jonda,et al.  Investigation of the Electronic Properties of Organic Light-Emitting Devices by Impedance Spectroscopy , 1999 .

[45]  W. Jaegermann,et al.  Electronic Energy Levels of Organic Dyes on Silicon: A Photoelectron Spectroscopy Study of ZnPc, F16ZnPc, and ZnTPP on p-Si(111):H , 2004 .

[46]  Tung‐Hui Ke,et al.  Impedance spectroscopy and equivalent circuits of conductively doped organic hole-transport materials , 2010 .