Electronic structure of the organic semiconductor copper phthalocyanine and k cupc studied. Properties as organic semiconductors for their application in optoelectronic devices m. Phthalocyanines have a great technological potential 5 in areas related to intrinsic semiconductors, chemical sensors, nonlinear optics, laser recording materials, information storage systems, electrochromic display devices, and liquidcrystal color display applications, among others 8, 9. Melville, a brendan mirka, a rosemary cranston a and benoit h. Metal phthalocyanines are organic dyes having high thermaland photostability and promising for application as photocatalysts, semiconductors, and photosensitizers for photodynamic cancer therapy. Mesotetrapyrenylporphyrin and its metal co ii, cu ii, ni ii and zn ii complexes were synthesized, characterized and studied for their spectral, electrochemical and energy transfer properties. But the application of phthalocyanines in the industry began as a consequence of their inherent dark greenblue color, and for this reason they have been an important article of commerce for years as. Phthalocyanines for otfts unsubstituted rigid phthalocyanine compounds for otfts. Lessard many healthrelated diagnostics are expensive, time consuming and invasive. This type of device requires semiconductors characterized by low reorganization energies and strong intermolecular electronic interaction. Green photoluminescence was observed in dilute solutions. P and n type copper phthalocyanines as effective semiconductors in organic thinfilm transistor based dna biosensors at elevated temperatures nicholas t. Hybrid dye sensitized solar cells based on titanium.
Understanding the dependence of transport parameters on. The metal phthalocyanines were characterized by recording the xray diffractograms. We synthesized three novel sipcs using axial substitution and examined their performance as the act. Pdf structure and electronic properties of phthalocyanine films. Phthalocyanine is of course closely related to the highly coloured porphyrins which are classed as polyene chromogens, and contain no donor or acceptor groups. Efficient synthesis of silicon phthalocyanines sipc eliminating the strenuous.
Jaeger, fan, bard sensitization of semiconductors with phthalocyanine 2593 2. Vectorial diffusion for facile solutionprocessed self. Quantumchemical calculations show a considerable stabilization of the homo and lumo. Spectral sensitization of the semiconductors nti02 and nw03 with metal phthalocyanines alain giraudeau, furen f. Phthalocyanines pc are a chemically versatile group of organic semiconductors that have been successfully employed as electroactive elements in a number of electronic devices including advanced photovoltaics 1, 2, sensors 3, fieldeffect transistors 4, nonlinear. The applications of synthesized compounds in schottky barrier diodes were investigated. This study refers to the doping of organic semiconductors by a. All newly synthesized compounds were characterized by elemental analysis, ftir, uvvis, 1 hnmr, malditof ms, and gcms techniques.
The pyrenyl substituents and the porphyrin core remain essentially. The interest for glycosylated metal phthalocyanines was stimulated by comparing the extensive. Usually, the impurities can be either 3rd group elements or 5th group elements. However, its hard to apply this tuning protocol to the flexible class of carbonbased semiconductors. Copper phthalocyanine cupc single crystals were grown by physical vapor. Fluorescence cence type ii reactions type i reactions radicals bacteria fungi virus pollutant chemicals s1 s0 s0 s3 1 o 2 3 o 2 e transfer, o,2 f. Silicon phthalocyanines as ntype semiconductors in organic thin film transistors. The new compounds have been characterized by 1 h and c using nmr, ftir, and uvvis.
Melville, brendan mirka, rosemary cranston and benot h. Peripherally fullerenefunctionalised asymmetric phthalocyanines. In recent years szentgyorgyi has directed attention to the possible importance of the electrical properties of organic molecules in biochemical catalysis1 and. Phthalocyanines pcs are macrocyclic compounds, and have attracted much attention due to their unique physical and chemical properties 1, 2. Lessard1, 1 university of ottawa, department of chemical and biological engineering, 161 louis pasteur, ottawa, ontario, k1n 6n5. Pdf organic semiconductors of phthalocyanine compounds for. Phthalocyanines of some metals for example, copper and of. The key synthetic step is the efficient eightfold oxidation of sulfanyl sr into sulfonyl so2r functions in the precursor pcsr8. Metal phthalocyanines are considered to be prominent candidates for designing organic semiconductors. The organic semiconductors are also studied as interfacial layers in metal semiconductor structures, as these semiconductors can modify the.
The absorption, fluorescence, and electrochemical properties were also studied. Electronic structure of the organic semiconductor copper. Phthalocyanines pc produced for 75 years as blue and green pigments are the most important organic. Phthalocyanines with electrondonating and electronwithdrawing substituents in the same benzene ring acknowledgements. Silicon phthalocyanines sipcs represent a large class of molecules that have been studied as donors, acceptors and ternary additives in organic photovoltaics but not in organic thinfilm transistors otfts. Review of the electrical, optical, structural and schottky.
The continuing development of organic semiconductors 1 will bring about flexible displays 2, radiofrequency identification tags 3, improved lighting technologies 4, efficient sensors 5,6 and. Simplified picture of the use of phthalocyanines, titanium oxide and conducting glass. Molecules of phthalocyanine and its complex salt possess a flatplane structure. A new class of synthetic dyes is phthalocyanine, systematically investigated by linstead together with coworkers, is of great interest not only in connection with their application as dyes, but also for biochemistry in form of its close structural resemblance to porphyrins, which generate base for many important natural pigments hemoglobin, chlorophyll. Electronic and structural properties of thin films of. Journal of porphyrins and phthalocyanines online ready. Professor drew brodeur department of chemistry and biochemistry, worcester polytechnic institute figure1. High mobility singlecrystal fieldeffect transistors based on. Extrinsic semiconductors the extrinsic semiconductors are those in which impurities of large quantity are present. Silicon phthalocyanines as ntype semiconductors in organic thin film transistors owen a. Preparation, characterization and biological activity of chromium. However, it is difficult to find a suitable solvent and solution process for most semiconductors. Phthalocyanine is a tetrapyrrole fundamental parent that consists of four isoindole type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.
Experiment and simulation xialing chen, phd university of pittsburgh, 2015 this dissertation focuses on the charge transport of organic semiconductors, particularly in the presence of traps and defects. Abstract thin films of perfluorinated phthalocyanines f16pc show promise as molecular semiconductors in organic field effect transistors. Journal of porphyrins and phthalocyanines vol 10, no 10. Synthesis of peripherally tetrasubstituted phthalocyanines. Charge transport properties of metal metal phthalocyanine nsi. However, enhancing ntype characteristics and air stability in these compounds have been the. Structure and electronic properties of phthalocyanine films on metal and semiconductor substrates. Spectral sensitization by metalfree phthalocyanine h2pc films was observed on various semiconductor electrodes single crystal ntio2, nsrtio3, nwo3. We study charge transport in molecular organic semiconductors using two terminal and three terminal field effect transistor devices. Electrical engineers can finetune the energetics of rigid photovoltaics and transistors by blending different semiconducting materials. Pdf organic semiconductors of phthalocyanine compounds. Studies on substituted cobalt ii phthalocyanines shoukat ali r a, j keshavayya and keerthi kumar c t.
Silicon phthalocyanines as ntype semiconductors in. Phthalocyanines pcs belong to the most studied organic functional. Bard contribution from the department of chemistry, the university of texas at austin, austin, texas 7871 2. This paper describes the synthesis and physicochemical characterization of novel metalfree phthalocyanines pcso2r8, bearing eight peripheral alkylsulfonyl substituents. Dft optimization was carried out to gain an insight into the interactions between the porphyrin. Films of organic polymers were prepared and investigated as insulating layers in contact with phthalocyanines as organic semiconductors for the use in organic field effect transistors ofet. Relative energy levels of semiconductors,is h2pc and redox couples. Bard department of chemistry, the university of texas at austin, austin, texas 78712 received. Metalfree phthalocyanines bearing eight alkylsulfonyl. Fluorinated phthalocyanines as molecular semiconductor thin films. Thin insulating polymer films as dielectric layers for phthalocyaninebased organic field effect transistors. It is a tetrapyrrole fundamental parent and a member of phthalocyanines. A synthetic approach to asymmetric phthalocyanines with.
New metalfree and metallophthalocyanine compounds zn, co, ni, and cu were synthesized using 2hydroxymethyl1,4benzodioxan and 4nitrophthalonitrile compounds. The very important blue pigment copper phthalocyanine is a tetraazatetrabenzoporphin and the basic polyene chromogen of the molecule is as in 119, which has an azaannulene type ring. Review of the electrical, optical and structural properties in phthalocyanines 1. Solution processibility is one of the most intriguing properties of organic semiconductors. Organic semiconductors of phthalocyanine compounds for.
In order to increase the species of organic semiconductors, new znphthalocyaninesbased organic materials were synthesized and characterized. Solution processible organic semiconductors have attracted great attention in recent years due to their applications in printable electronics, such as organic thinfilm transistor otft. Extrapolations of the applicability of these models to amorphous semiconductors. Various functional phthalocyanines as well as their tetrapyrrole analogs, porphyrins, have been extensively studied as organic semiconductors since the first report of organic field effect transistors ofets in 1986. Rather than attempting to ultimately pure materials, intentional. Pdf p and n type copper phthalocyanines as effective. Using phthalocyanines as examples, we achieve unification of carrier mobility between the different configurations in a gaussian density of states. Properties of phthalocyanines and phthalocyanine derivatives are being studied. Synthesis, characterization and photocatalytic studies of. Synthesis, spectral, and electrochemical characterization of the first arsenicvphthalocyanines. Structure and electronic properties of phthalocyanine films on metal and semiconductor substrates ieva bidermane to cite this version. We synthesized three novel sipcs using axial substitution and examined their performance as the active layer in bottomgate bottomcontact bgbc otfts. Pdf various functional phthalocyanines as well as their tetrapyrrole analogs, porphyrins, have been extensively studied as organic.
December 14, 1982 the behavior of photoelectrochemical pec cells composed of sn02 or pt. Band structure engineering in organic semiconductors science. The design and synthesis of novel phthalocyanine systems. P and n type copper phthalocyanines as effective semiconductors in organic thinfilm transistor based dna biosensors at elevated temperatures january 2019 rsc advances 94. Based on the impurities present in the extrinsic semiconductors, they are classified into two categories. For example, metal phthalocyanines mpcs are only soluble in non. Structure and electronic properties of phthalocyanine. A preliminary investigation into hybrid photovoltaic cells. Synthesis, characterization and semiconducting properties. Chromium phthalocyanine, nonsolvent method, biological.
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