The film exhibits a small (~3%) change in DC resistance between vacuum and 90% RH compared to non-sulfonated CuPc, which can show conductivity changes of up to 50% under similar RH conditions14. Talanta [14] The electrochemical properties of MPc make them effective electron-donors and -acceptors. Humidity effect on optical properties. Kinetics modelling. Higher yields may be achieved with the solvent process (> 95%) than with the baking process (70 to 80%), so that the solvent process has initially simulated more interest. Solar Energy Materials and Solar Cells Product Number: All applicable American Elements product codes, e.g. Japanese Journal of Applied Physics Ivanov, I. N., Dabestani, R., Buchanan, A. for more information. Personal precautions, protective equipment and emergency proceduresAvoid dust formation. Please Contact Us For the PFO reaction model, we used \(\,{M}_{e}=\,{M}_{e1}+{M}_{e2}\). [5] They are less thermally stable and often can not be sublimed. 2a. [17] The abbreviation "CuPc" is also used.[18]. 29, 814818 (2009). If material is not included in the articles Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. COPYRIGHT 1997-2022 AMERICAN ELEMENTS. Five different polymorphs have been identified:[36][37][38][39] phases , , , and . C.B. The Journal of Physical Chemistry B The number of electrons in each of copper's shells is 2, 8, 18, 1 and its electron configuration is [Ar]3d10 4s1. Directed electron transfer in Langmuir-Schfer layers of porphyrin-fullerene and phthalocyanine-fullerene dyads in inverted organic solar cells. Thank you for visiting nature.com. 2005;246:327333. It is highly valued for its superior properties such as light fastness, tinting strength, covering power and resistance to the effects of alkalis and acids. [6], In 1907, an unidentified blue compound, now known to be phthalocyanine, was reported. 156, 210 (2010). Error bars correspond to linear fitting errors. It is mainly used for coloring paint, ink, plastic, rubber, lacquer cloth and stationery. A soluble derivative of copper phthalocyanine, that is 2,9,16,23-tetra carboxyl copper phthalocyanine (CuTCPc), is synthesized in this paper. Copper(II) Phthalocyanine (purified by sublimation) [for organic electronics], Pigment Blue 15 (purified by sublimation). Characterization of evaporated trivalent and tetravalent phthalocyanines thin films: different degree of organization. 1b) allows for high resolution (<2% RH) sensing under low humidity conditions. These findings suggest the potential of the examined ZnPc-BODIPY pentad to be efficient photosynthetic antenna in the Information on basic physical and chemical propertiesa) Appearance Form: powderb) Odour odourlessc) Odour Threshold No data availabled) pH No data availablee) Melting point/freezing point350 C (662 F)f) Initial boiling point and boiling rangeNo data availableg) Flash point ()No data availableh) Evaporation rate No data availablei) Flammability (solid, gas)No data availablej) Upper/lower flammability or explosive limitsNo data availablek) Vapour pressure < 0.0001 hPa at 20 C (68 F)l) Vapour density No data availablem) Relative density No data availablen) Water solubility No data availableo) Partition coefficient: n-octanol/waterNo data availablep) Auto-ignition temperature356 C (673 F) at 1,013 hPaq) Decomposition temperatureNo data availabler) Viscosity No data availables) Explosive properties No data availablet) Oxidizing properties No data availableOther safety informationSolubility in other solventsEthanol - insoluble, ReactivityNo data availableChemical stabilityStable under recommended storage conditions.Possibility of hazardous reactionsNo data availableConditions to avoidNo data availableIncompatible materialsStrong oxidizing agentsHazardous decomposition productsHazardous decomposition products formed under fire conditions. examined by femtosecond and nanosecond laser flash photolysis to explore its photoinduced intramolecular events from the form = 1.61-1.62 Accosperse cyan blue GT Aqualine blue Bahama blue BC Bermuda blue Blue GLA Blue phthalocyanine .alpha.-form . The excitation transfer from the singlet BODIPY to, ZnPc is envisioned due to good spectral overlap of the BODIPY emission and ZnPc absorption spectra. Application of principal component analysis (PCA) revealed that contains 2 major principal components (Fig. Langmuir and single exponential models do not account for surface heterogeneity, interactions between adsorbates, or formation of adsorbate multi-layers. government site. government site. [12] Using such methods, approximately 57,000tonnes (63,000Imperial tons) of various phthalocyanines were produced in 1985. CuPc (copper phthalocyanine) was first prepared in 1927 by the reaction of copper(I) cyanide and o-dibromobenzene, which mainly produces colorless phthalonitrile as well as an intensely blue by-product. Journal of Optoelectronics and Advanced Materials b8$B "/2y0b?C%-9#Q\X2iDaRh5rEZ@eZJ. Frequency shift of the QCM crystals was converted to mass change using the well-known Sauerbrey equation25. (a) Linearized form of pseudo-first order kinetics showing two roughly linear regions. Such compounds are prepared by treating CuPc with chlorine, bromine or oleum. The results suggest that rapid H2O adsorption takes place at hydrophilic sulfonyl/salt groups on domain surfaces at low RH, while slow adsorption and diffusion of H2O into CuPcTs crystallites leads to a mixed CuPcTs-H2O phase at RH > 60%, resulting in high frequency dielectric screening of the film by water and dissociation of Na+ from CuPc(SO3-)4 ions. Aqueous solubility of copper phthalocyanine-3,4',4,4'-tetrasulfonic acid tetrasodium salt (CuPcTs) enables fabrication of flexible electronic devices by low cost inkjet printing. CAS While the concentration of component-3 remains relatively constant throughout the measured RH range, the component-2 fraction increases sharply at RH 60%. The geometry optimization showed that the phthalocyanine moiety is completely symmetric and form https://doi.org/10.1038/s41598-017-10401-2, DOI: https://doi.org/10.1038/s41598-017-10401-2. Sponsored Content is a special paid section where industry companies provide high quality, objective, non-commercial content around topics of interest to the PCI audience. Your email address will not be stored! Insights into the modeling of adsorption isotherm systems. Upon formation of H2O multilayers and merging of adjacent adsorbed H2O clusters, interactions between mobile Na+ ions, CuPc(SO3 [17] Sulfonated phthalocyanine has been found to cause neuroanatomical defects in developing chicken embryos when injected directly into incubating eggs. block. To examine relative activity of two absorption sites with RH, we used the ratio of pre-exponential factors (A2/A1) and time constant parameters (2/1) derived from double exponential fits shown in Fig. The hydrophilic site is associated with the Na+SO3 Although the units for first and second order rate constants are different, the PSO rate constant \({k}_{2}\) clearly resembles behavior of the PFO rate constant \(\,{k}_{1-1}\), and its value lies between the values of \(\,{k}_{1-1}\) and \({k}_{1-2}\) because \(\,{k}_{2}\) describes a combination of two sequentially-occurring reactions with rates \(\,{k}_{1-1}\,\,\)and \(\,{k}_{1-2}\). 1 represents 2 distinct sequentially-occurring PFO reactions. HWKofvEM The applications of CuTCPc as donor and interlayer materials in solar cell devices are investigated. Aziz, F. et al. doi: 10.1149/1.2129940. Del Cano, T., Parra, V., Rodrguez-Mndez, M., Aroca, R. & De Saja, J. Multimodality of Structural, Electrical, and Gravimetric Responses of Intercalated MXenes to Water. The requested analytical chart is not available. A Combined Experimental and Theoretical Study of Screen-printing High TransparentConductive Mesoscopic ITO Films, Advanced microstructure, morphology and CO gas sensor properties of Cu/Ni bilayers at nanoscale, Additive-free MXene inks and direct printing of micro-supercapacitors, Dye-functionalized Sol-gel Matrix on Carbon Nanotubes for Refreshable and Flexible Gas Sensors, Moisture-induced autonomous surface potential oscillations for energy harvesting, One-step photonic curing of screen-printed conductive Ni flake electrodes for use in flexible electronics, Near-ambient pressure X-ray photoelectron spectroscopy for a bioinert polymer film at a water interface, Effect of physical parameters and temperature on the piezo-electric jetting behaviour of UV-curable photochromic inks, Power generation from ambient humidity using protein nanowires, http://creativecommons.org/licenses/by/4.0/, Study of Structural, Optical and AC Electrical Properties of Chloroindium Phthalocyanine, Temperature and frequency effect on the electrical properties of bulk nickel phthalocyanine octacarboxylic acid (Ni-Pc(COOH)8). Publisher's note: Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. 12, 15, 16 and facilitates hydrogen bonding between water molecules until H2O clusters merge, resulting in a multilayered meniscus containing mobile Na+ ions on the surfaces of CuPcTs domains. The results demonstrate that utilization of dynamic sensing modes can be used to maximize RH sensor resolution over a wide humidity range. When CuTCPc acts as an interlayer, the performance of the device ITO/CuTCPc/P3HT:PCBM/Al is improved: J(SC) increases to 3.12 mA/cm2, V(OC) increases to 0.59 V, FF increases to 33.8%, and the corresponding nu is 0.62%. & Garca-Valenzuela, A. Adsorption kinetics of optochemical NH 3 gas sensing with semiconductor polyaniline films. What is the longest-running laboratory experiment? Please note that we cannot offer bulk quantities for some products. To prepare these complexes, the phthalocyanine synthesis is conducted in the presence of metal salts. Kinetics of H2O adsorption visibly change as P/P0 increases; i.e. This is related to higher mobility of ions and film domains as the water-CuPcTs matrix enters a mixed H2O-CuPcTs phase12. * Items in stock locally ship in 1-2 business days. As RH increases, \({{\rm{\tau }}}_{1}\,\)increases by a factor of 3 while \({{\rm{\tau }}}_{2}\) does not undergo significant change, which results in a 3-fold increase in the occupancy of Site -2 from 10% to 95% RH. One of the most common donor/acceptor architectures is CuPc/C60 (buckminsterfullerene) which rapidly became a model system for the study of small organic molecules. PUGVIEW FETCH ERROR: 403 Forbidden National Center for Biotechnology Information 8600 Rockville Pike, Bethesda, MD, 20894 USA Contact Policies FOIA HHS Vulnerability Disclosure National Library of Medicine Water saturation of the sulfonyl groups leads to dissociation of Na+ ions from SO3 517, 20162022 (2009). Figure6a summarizes the results of CuPcTs RH sensitivity as estimated using different measured modes. 13, 851 (1939). Soluble copper phthalocyanine dyes and their use, [Cu]. Materials Science and Engineering: C Optical thickness of the CuPcTs film was estimated from SPE data. & Sigman, M. E. Fluorescence decay study of anisotropic rotations of substituted pyrenes physisorbed and chemically attached to a fumed silica surface. 1980;127:15061517. There has since been significant research on H2Pc and MPc resulting in a wide range of applications in areas including photovoltaics, photodynamic therapy, nanoparticle construction, and catalysis. Muckley ES, Naguib M, Wang HW, Vlcek L, Osti NC, Sacci RL, Sang X, Unocic RR, Xie Y, Tyagi M, Mamontov E, Page KL, Kent PRC, Nanda J, Ivanov IN. Phthalocyanine and derived metal complexes (MPc) tend to aggregate and, thus, have low solubility in common solvents. [N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2, N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1, ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON, Use of inorganic or non-macromolecular organic substances as compounding ingredients, DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR, ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. excited BODIPY. The rate constant \({k}_{2}\) was extracted and compared to \({k}_{1-1}\) and \({k}_{1-2}\) (FigureS4). : 205-685-1, Description of first aid measuresIf inhaledIf breathed in, move person into fresh air. Do Kim, Y., Kim, J. P., Kwon, O. S. & Cho, I. H. The synthesis and application of thermally stable dyes for ink-jet printed LCD color filters. Muckley, E.S., Jacobs, C.B., Vidal, K. et al. help you have the best experience while on the site. If not breathing, give artificial respiration.In case of skin contactWash off with soap and plenty of water.In case of eye contactFlush eyes with water as a precaution.If swallowedNever give anything by mouth to an unconscious person. 146, 794799 (1999). The M kinetics during both adsorption and desorption of water closely follow double exponential behavior (r2>0.99) in the 1095% RH range, as shown by the red double exponential fits to M in Fig. This trend is opposite to that of n (optical-mode sensing), which exhibits high RH dependence at P/P0>0.6 (Figs3a and S5a) and thus represents the most sensitive (<2% RH) detection mode at high RH. Box 2008, Oak Ridge, TN, 37831-6496, USA, Eric S. Muckley,Christopher B. Jacobs,Keith Vidal,Nickolay V. Lavrik,Bobby G. Sumpter&Ilia N. Ivanov, Bredesen Center, University of Tennessee Knoxville, 444 Greve Hall, 821 Volunteer Blvd, Knoxville, TN, 37996-3394, USA, Computer Science and Mathematics Division, Oak Ridge National Laboratory, Oak Ridge, TN, 37831, USA, You can also search for this author in Film thickness was controlled during deposition by spin-coating at 3000 RPM for 30seconds, resulting in ~50nm thick films. Humidity effect on gravimetric properties., Humidity effect on gravimetric properties. The basic copper phthalocyanine has a very low solubility in water (0.009 mg/L) and in octanol (0.0004 mg/L). Before Adsorption at these sites does not lead to significant changes in optoelectronic properties of the film. The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request. [17] Silicon and zinc phthalocyanines have been developed as photosensitizers for non-invasive cancer treatment. Sorry for the inconvenience. 74160,[13][14][15] and British Rail Blue. Pseudo-first order, pseudo-second order, and double exponential fits were used to model kinetics of H2O adsorption on CuPcTs film. Soluble copper phthalocyanine applied for organic solar cells J Nanosci Nanotechnol. Accessibility Visit our privacy The first step is associated with adsorption of H2O on hydrophilic sulfonyl sites at the periphery of CuPcTs grains. The transition in C1 occurs in the same RH range (5070%) at which significant changes in optical constants, bandgap, and film thickness occur. The .gov means its official. 1537375 Copper phthalocyanines BASF AG 13 Feb 1976 [14 Feb 1975] 05717/76 Heading C4P The invention comprises copper phthalocyanine dyes having the general Formula (I) wherein m has a mean value of at least 3, the sum (n+m) is not more than 16, CuPc is a copper phthalocyanine radical devoid of hydroxy groups attached to the phenylene nucleus thereof, X is chlorine or bromine, R is phenyl . The rapid thickness change at RH>70% is consistent with formation of a mixed H2O-CuPcTs phase facilitated by hydrogen bonding between H2O adsorbates and gas-phase water molecules16, 17, 38. Research and sample quantities and hygroscopic, oxidizing or other air sensitive materials may be packaged under argon or vacuum. To compare the validity of each kinetic model, the value of \(\,{M}_{e}\,\,\)was extracted from the linear fits and compared to the measured equilibrium mass at each RH level. perfect square planar complex with zinc. Enhanced photocurrent and stability of organic solar cells using solution-based TS-CuPc interfacial layer. Sensors and Actuators B: Chemical Novel photoactive fluorene-based terpolymers incorporating carbazole for photovoltaic application. Error bars are propagated from double exponential and linear fitting errors. for more information. CAS 1537375 Copper phthalocyanines BASF AG 13 Feb 1976 [14 Feb 1975] 05717/76 Heading C4P The invention comprises copper phthalocyanine dyes having the general Formula (I) wherein m has a mean value of at least 3, the sum (n+m) is not more than 16, CuPc is a copper phthalocyanine radical devoid of hydroxy groups attached to the phenylene nucleus thereof, X is chlorine or bromine, R is phenyl optionally substituted by one or more substituents which do not confer solubility in water, the groups R may be the same or different and if n is more than one, the groups X may be the same or different.
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