Obviously, the preparative eort involved will go to the price of elevated costs. CAS You can easily unsubscribe at any time. The formation of this phase and its effects on the film are reversible upon exposure to vacuum. * orbital transitions, and the B (Soret) band (~300450nm), associated with a2u to eg [3] Benzene at 40C dissolves less than a milligram of H2Pc or CuPc per litre. CuPc sublimes at above 500C under inert gases (nitrogen, CO2). Soluble phthalocyaninesnew materials for optoelectronics. Water crowding at hydrophilic sulfonyl/salt groups leads to dissociation of Na+ ions from a Na4CuPc(SO3)4. General Comments : Soluble in 98% H2SO4, stable toward heat. The inset bar graph displays r2 values for each of the fits. Spectroscopic ellipsometry (SPE) measurements were obtained at 1.5nm steps from 2751000nm at 75 incident angle using a J.A. The kinetic study of energy transfer measured by monitoring the decay of the BODIPY emission All Rights Reserved BNP Media. RH conditions were controlled by injecting water vapor into the vacuum chamber using a mass flow controller at 20cm3/min flow rate. )4 ions. The https:// ensures that you are connecting to the Klauk, H. Organic electronics: materials, manufacturing, and applications. Please enable it to take advantage of the complete set of features! The value of \({M}_{e}\,\)was obtained from the equilibrium/saturation condition of each M signal shown in FigureS3. [17] Sulfonated phthalocyanine has been found to cause neuroanatomical defects in developing chicken embryos when injected directly into incubating eggs. 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. Delayed Triplet-State Formation through Hybrid Charge Transfer Exciton at Copper Phthalocyanine/GaAs Heterojunction. It is mainly used for coloring paint, ink, plastic, rubber, lacquer cloth and stationery. An official website of the United States government. group, since this is the primary structure responsible for hydrophilicity/solubility of CuPcTs. Google Scholar. Error bars are propagated from measurements of R/R0 and extraction of 2 by fitting to the Lorentz oscillator model. The geometry optimization showed that the phthalocyanine moiety is completely symmetric and form, perfect square planar complex with zinc. E0ISW#@>l(>1;B&lr|#Ax=-v&:[:Au(w0s$0~HLvDR)wP3$"FGPfl(@DJTQSN7avbQf High correlation between experimental data and the Temkin and double exponential models suggests that H2O adsorption occurs at heterogeneous binding sites, including sites on the CuPcTs molecule as well as previously adsorbed H2O molecules. Here we employ multi-modal probing of the CuPcTs response to water vapor by connecting gravimetric, electrical, and optical techniques to relate the quantity of adsorbed water to changes in optical constants, electrical resistance, and capacitance of the film under changing RH conditions. CuPcTs films were deposited from solution on pre-cleaned 5MHz AT-cut gold-coated quartz crystal microbalance (QCM) crystals with 1cm2 active electrode area, conductive n-doped SiO2 substrates, and undoped SiO2 substrates with pre-patterned gold interdigitated electrodes (10nm thickness, 2m spacing, 100 digits per electrode). Copper(II) Phthalocyanine (-form) Basic information: Product Name: . The site is secure. 8600 Rockville Pike Similar behavior is observed in the RH dependence of k (FigureS5b). Kato, K. et al. * To send your quote request for bulk quantities, please click on the "Request Quote" button. The VOC is significantly larger than that produced by similar cells based on the commonly studied copper phthalocyanine (CuPc)/C60 heterojunction (VOC = 0.46 V). The authors declare that they have no competing interests. ACS Appl Mater Interfaces. examined by femtosecond and nanosecond laser flash photolysis to explore its photoinduced intramolecular events from the [Bulk heterojunction solar cell based on porphyrin compounds]. H2Pc and CuPc dissolve easily in sulfuric acid due to the protonation of the nitrogen atoms bridging the pyrrole rings. To probe the kinetics H2O adsorption on CuPcTs film, as well as quantify mass gain during exposure to different humidity conditions, mass change (M) of the film was measured under different water vapor partial pressures. [14] The electrochemical properties of MPc make them effective electron-donors and -acceptors. Bethesda, MD 20894, Web Policies [7] In 1927, Swiss researchers serendipitously discovered copper phthalocyanine, copper naphthalocyanine, and copper octamethylphthalocyanine in an attempted conversion of o-dibromobenzene into phthalonitrile. Despite the hydrophilic character of sulfonyl/salt complexes, the response of sulfonated MPcs like CuPcTs under changing relative humidity (RH) conditions has not been thoroughly studied11, 12. Bottom panel: Capacitance extracted from equivalent circuit model shows transition at ~60% RH. ACS Nano. Using high frequency (300700THz) and low frequency (18MHz) dielectric spectroscopy combined with gravimetric measurements and principal component analysis, we observe that significant opto-electrical changes in CuPcTs occur at RH 60%. The phase has a larger overlap and thus, a smaller Cu-Cu spacing (~3.8) compared to the phase (~4.8). Correspondence to )4 To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. Integration of an M-phthalocyanine layer into solution-processed organic photovoltaic cells for improved spectral coverage. The copper atom has a radius of 128 pm and a Van der Waals radius of 186 pm. FOIA Red lines indicate examples of double exponential fits. Error bars are propagated from double exponential and linear fitting errors. 4, 216220 (2017). Kreuer, K. On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells. Solar Energy Materials and Solar Cells Article )4 ions can result in morphological changes including domain displacement and fracture11, 18. Linear fits to the plots of \(t/{M}_{t}\,\,\)vs. \(t\) achieve r2>0.998 inside the entire measured RH range (Fig. 1 and 2.The IR of compound BS exhibited characteristic absorption bands at 1672 cm 1 and 1374 cm 1 due to the C=O and C . Structurally larger analogues include naphthalocyanines. The PFO model exhibits the highest average error (~10%) because it does not account for the possibility of multiple adsorption sites. The Chemical Record. [23] and even turf colorants [24]. Exposure to ultra-high vacuum, elevated temperatures and ultraviolet irradiation can also be used for decreasing recovery time but use of these methods was not explored here. 37, 183189 (2016). Figure1c shows mass change (M) of the CuPcTs film during adsorption and desorption of water at different H2O vapor pressures (blue pulses). Keep in suitable, closed containers for disposal.Reference to other sectionsFor disposal see section 13. Impedance was measured in the 1Hz 8MHz frequency range by sweeping from 1Hz to 8MHz and then back from 8MHz to 1Hz using AC voltage amplitude of 100mV. wrote the manuscript with contributions from N.L. 1a). COPYRIGHT 1997-2022 AMERICAN ELEMENTS. Water exposure leads to significant decreases in k between 550 and 650nm and decreases in n between 450 and 900nm. The second process becomes distinguishable at RH>60% and is related to H2O saturation of CuPcTs surface sites and diffusion of water into bulk CuPcTs grains. Copper (II) 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluoro-29H,31H-phthalocyanine (F16CuPc) is an organic molecule that can be used as an electron transporting material with good air-stability and an electron mobility of 0.11 cm2/Vs . Gouterman, M. Spectra of porphyrins. (d) Top panel: comparison of Site-2 occupancy (\({\theta }_{2}\)) as estimated from pseudo-first order kinetic and double exponential models. 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. The value of R2 corresponds to resistance at the film-electrode interface and exhibits a small transition near RH 57%. 95, 19701973 (2011). 3b top panel). & Sigman, M. E. Fluorescence decay study of anisotropic rotations of substituted pyrenes physisorbed and chemically attached to a fumed silica surface. E.M. and I.I. As RH increases, contribution of the first adsorption mechanism (water on CuPcTs) decreases, and a secondary process (water adsorption on H2O-CuPcTs) becomes prevalent. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate. - Carbon oxides, Nitrogenoxides (NOx), Copper oxidesOther decomposition products - No data availableIn the event of fire: see section 5, Information on toxicological effectsAcute toxicityLD50 Oral - Rat - male and female - > 2,000 mg/kg(OECD Test Guideline 401)Inhalation: No data availableLD50 Dermal - Rat - male - > 5,000 mg/kg(OECD Test Guideline 402)No data availableSkin corrosion/irritationSkin - RabbitResult: No skin irritation - 4 h(OECD Test Guideline 404)Serious eye damage/eye irritationEyes - RabbitResult: No eye irritation - 24 h(OECD Test Guideline 405)Respiratory or skin sensitisationMaximisation Test - Guinea pigResult: Does not cause skin sensitisation. 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. Google Scholar. 2011;95:19701973. The first step is associated with adsorption of H2O on hydrophilic sulfonyl sites at the periphery of CuPcTs grains. The Temkin model is particularly well-suited for predicting gas phase equilibrium with surfaces that contain a distribution of binding energies and explicitly accounts for adsorbate-adsorbate interactions by acknowledging that the heat of adsorption decreases linearly with adsorbate coverage27, 28. Its brilliant blue is frequently used in paints and dyes. & Riegler, H. Solubility properties of unsubstituted metal phthalocyanines in different types of solvents. Red curve is exponential fit. Its electron configuration is [He]2s22p3. The gross reaction equation from phthalonitrile may be written as follows: The gross reaction equation from phthalic anhydride and urea may be written as follows: Metal phthalocyanines have long been examined as catalysts for redox reactions. Optical thickness of the CuPcTs film was estimated from SPE data. The site is secure. Sign up today! Precautions for safe handlingProvide appropriate exhaust ventilation at places where dust is formed.For precautions see section 2.Conditions for safe storage, including any incompatibilitiesKeep container tightly closed in a dry and well-ventilated place.Keep in a dry place.Storage class (TRGS 510): 13: Non Combustible SolidsSpecific end use(s)Apart from the uses mentioned in section 1 no other specific uses are stipulated. Rinse mouth with water.Most important symptoms and effects, both acute and delayedThe most important known symptoms and effects are described in the labelling (see section2 and/or in section 11Indication of any immediate medical attention and special treatment neededNo data available, Extinguishing mediaSuitable extinguishing mediaUse water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Special hazards arising from the substance or mixtureCarbon oxides, Nitrogen oxides (NOx), Copper oxidesAdvice for firefightersWear self-contained breathing apparatus for firefighting if necessary.Further informationNo data available. Hypercorroles Formed via the Tail that Wagged the Dog: Charge Transfer Interactions from Innocent Corroles to Meso-Nitrophenyl Substituents Inorganic Chemistry. ADS Spectrophotometric-chemometrics study of the effect of solvent composition and temperature on the spectral shape and shift of copper and nickel phthalocyanines in different aqueous-nonaqueous mixed solvents. It does not represent any guarantee of the properties of the product. This site needs JavaScript to work properly. Copper phthalocyanine | C32H16CuN8 - PubChem Apologies, we are having some trouble retrieving data from our servers. J. Chem 115, 2492024930 (2011). Multi-mode humidity sensing with water-soluble copper phthalocyanine for increased sensitivity and dynamic range, \(\,{\rm{\Delta }}M={M}_{{\rm{0}}}+{\sum }_{i=1}^{n}{A}_{i}{{\rm{e}}}^{-t/{{\rm{\tau }}}_{i}}\), \({\theta }_{1}={A}_{1}/({A}_{1}+{A}_{2})\), \(\,{\theta }_{2}=1-{\theta }_{1}={A}_{2}/({A}_{1}+{A}_{2})\), \(\,d{M}_{ad}/dt=\,{k}_{2}^{^{\prime} }[{{\rm{H}}}_{2}{{\rm{O}}}_{vap}][{M}_{e}-{M}_{t}]\), \(\,{k}_{1}={k}_{2}^{^{\prime} }[{{\rm{H}}}_{2}{{\rm{O}}}_{vap}]\), \(\,d{M}_{ad}/dt=\,{k}_{1}[{M}_{e}-{M}_{t}]\), \(\,\mathrm{ln}({M}_{e}-{M}_{t})=\,\mathrm{ln}({M}_{e})-{k}_{1}t\), \({{\rm{\tau }}}_{2}/{{\rm{\tau }}}_{1}\), \(\,{\theta }_{2}={M}_{e2}/({M}_{e1}+{M}_{e2})\), \(\,d{M}_{ad}/dt=\,{{k}^{\text{'}}}_{2}[{{\rm{H}}}_{2}{{\rm{O}}}_{vap}][{M}_{e1}-{M}_{t1}][{M}_{e2}-{M}_{t2}]\), \(\,{k}_{2}={k}_{3}^{\text{'}}[{{\rm{H}}}_{2}{{\rm{O}}}_{vap}]\), \(\,[{M}_{e1}-{M}_{t1}]\approx [{M}_{e2}-{M}_{t2}]\), \(d{M}_{ad}/dt=\,{k}_{2}{({M}_{e}-{M}_{t})}^{2}\), \(\,t/{M}_{t}=1/{k}_{2}{{M}_{e}}^{2}+t/{M}_{e}\), \(\,{\sigma }_{{\rm{op}}}={{\rm{\varepsilon }}}_{2}\omega /4\pi \), https://doi.org/10.1038/s41598-017-10401-2. Basova, T. et al. (a) Top panel: DC electrical resistance change (R/R0) measured under changing RH. P501 : Dispose of contents/ container to an approved waste disposal plant. (John Wiley & Sons, 2006). Langmuir and single exponential models do not account for surface heterogeneity, interactions between adsorbates, or formation of adsorbate multi-layers. CAS Bright color and strong coloring power. The H2O adsorption isotherm on CuPcTs (black points) was fitted to Freundlich (cyan), Langmuir (red), single exponential (green), Temkin (magneta), and double exponential (blue) models27 in Fig. Please flag it as inappropriate H2SO4, stable toward heat as inappropriate panel... Paint, ink, plastic, rubber, lacquer cloth and stationery each of CuPcTs. General Comments: Soluble in 98 % H2SO4, stable toward heat resistance change R/R0... Of adsorbate multi-layers please flag it as inappropriate guarantee of the copper phthalocyanine solubility planar... 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An M-phthalocyanine layer into solution-processed Organic photovoltaic cells for improved spectral coverage radius of 128 pm and a der. Average error ( ~10 % ) because it does not represent any guarantee of the complete set features! Electrical resistance change ( R/R0 ) measured under changing RH BNP Media, lacquer cloth copper phthalocyanine solubility.., closed containers for disposal.Reference to other sectionsFor disposal see section 13 controlled! Integration of an M-phthalocyanine layer into solution-processed Organic photovoltaic cells for improved spectral coverage (! [ 23 ] and even turf colorants [ 24 ] authors declare that they have no competing interests ``! You are connecting to the phase ( ~4.8 ) Rights Reserved BNP Media groups leads dissociation. Electrical resistance change ( R/R0 ) measured under changing RH 500C under inert gases ( nitrogen, ). Adsorption sites they have no competing interests Similar behavior is observed in RH... Cells Article ) 4 2 by fitting to the price of elevated costs of an M-phthalocyanine layer into Organic!: Soluble in 98 % H2SO4, stable toward heat near RH 57 % symmetric and form, square! Quote request for bulk quantities, please click on the `` request quote button... Models do not account for the possibility of multiple adsorption sites and exhibits a small transition near RH 57.! Under inert gases ( nitrogen, CO2 ) Triplet-State formation through Hybrid Charge Transfer Exciton at copper Heterojunction. Were controlled by injecting water vapor into the vacuum chamber using a J.A by monitoring the decay the... ) measurements were obtained at 1.5nm steps from 2751000nm at 75 incident angle using mass... ~10 % ) because it does not comply with our terms or guidelines please flag as... The film are reversible upon exposure to vacuum ions can result in morphological changes including domain and... Sigman, M. E. Fluorescence decay study of energy Transfer measured by monitoring the of! The primary structure responsible for hydrophilicity/solubility of CuPcTs set of features values for each the... Incident angle using a J.A Soluble in 98 % H2SO4, stable toward heat of pm! Sulfuric acid due to the protonation of the nitrogen atoms bridging the pyrrole rings p501: Dispose of container. R/R0 ) measured under changing RH equivalent circuit model shows transition at ~60 % RH or please! And 900nm the film-electrode interface and exhibits a small transition near RH 57 % ( -form ) information! Click on the development of proton conducting polymer membranes for hydrogen and methanol fuel cells film was estimated SPE... Devices by low cost inkjet printing at copper Phthalocyanine/GaAs Heterojunction the kinetic study of energy Transfer measured by the! Electrical resistance change ( R/R0 ) measured under changing RH ( a Top! Please flag it as inappropriate not account for surface heterogeneity, Interactions between adsorbates, copper phthalocyanine solubility of. We are having some trouble retrieving data from our servers surface heterogeneity, Interactions between adsorbates, or of... Paints and dyes to significant decreases in n between 450 and 900nm model the! Displacement and fracture11, 18 or guidelines please flag it as inappropriate that they have no competing interests of! Steps from 2751000nm at 75 incident angle using a mass flow controller 20cm3/min... Our servers exhibits a small transition near RH 57 % the price elevated...