copper phthalocyanine solubility

Molecule structure of Copper phthalocyanine (CAS NO.147-14-8): Molecular Weight: 576.06904 g/mol Molecular Formula: C 32 H 16 CuN 8 Melting Point: 600C (dec.) Water Solubility: <0.1 g/100 mL at 20 C H-Bond Acceptor: 8 Exact Mass: 575.079394 MonoIsotopic Mass: 575.079394 Topological Polar Surface Area: 98.9 Heavy Atom Count: 41 (C 8 H 4 N 2) 4 H 2 = H 2 Pc has a two-dimensional geometry and a ring system consisting of 18 -electrons. doi: 10.1016/j.solmat.2011.01.042. Solar Energy Materials and Solar Cells. Phthalocyanine and derived metal complexes (MPc) tend to aggregate and, thus, have low solubility in common solvents. Applied surface science Phthalocyanines are structurally related to other tetrapyrrole macrocyles including porphyrins and porphyrazines. The dye derived from cobalt phthalocyanine and an amine is Phthalogen Dye IBN. Humidity effect on gravimetric properties. As RH increases, the rate associated with rapid adsorption (\({k}_{1-1}\)) decreases, while the rate of slow adsorption (\({k}_{1-2}\)) generally increases. for more information. (d) Top panel: comparison of Site-2 occupancy (\({\theta }_{2}\)) as estimated from pseudo-first order kinetic and double exponential models. %PDF-1.4 % Klauk, H. Organic electronics: materials, manufacturing, and applications. Since the electron transfer from the singlet ZnPc to, BODIPY is thermodynamically not feasible, the singlet ZnPc decayed to populates the triplet ZnPc, in addition to the grounds, state. Moradian S, Dezhampanah H, Ghasemi JB, Behnejad H. Spectrochim Acta A Mol Biomol Spectrosc. pails, fiber and steel drums to 1 ton super sacks in full container (FCL) or truck load (T/L) quantities. The CuPcTs-H2O interaction can be tracked using a combination of gravimetric, optical, and electrical sensing modes, enabling accurate ( 2.5%) sensing in the ~0-95% RH range with a detection limit of less than 0.1% RH. While optical response of sulfonated phthalocyanines has been well-studied in solution, less information is available about water interaction with solid films15, 19. Research and sample quantities and hygroscopic, oxidizing or other air sensitive materials may be packaged under argon or vacuum. Tosun, . Unable to load your collection due to an error, Unable to load your delegates due to an error, Humidity effect on gravimetric properties. [30] Journal of Chemical & Engineering Data Muckley, E. S. et al. [17] Sulfonated phthalocyanine has been found to cause neuroanatomical defects in developing chicken embryos when injected directly into incubating eggs. Pseudo-first order, pseudo-second order, and double exponential fits were used to model kinetics of H2O adsorption on CuPcTs film. Water Research CAS Harrington, D. A. I.I. [17] No evidence indicates carcinogenic effects. 2c), indicating that the value of M closely follows PSO reaction kinetics due to the presence of 2 different adsorption sites. Your email address will not be stored! Prof.Fadlelmoula A.Idris Cite. Journal of Molecular Spectroscopy It is composed of four isoindole units linked by a ring of nitrogen atoms. The Journal of Physical Chemistry C Park, J. H., Lee, S. & Kummel, A. C. Domain fracture and recovery process of metal phthalocyanine monolayers via NO2 and H2O. PubMed The cantilever was operated in semi-contact (tapping) mode at 73kHz tip resonance frequency with a line scan rate of 0.7Hz. Improvement of the photovoltaic parameters of perovskite solar cells using a reduced-graphene-oxide-modified titania layer and soluble copper phthalocyanine as a hole transporter. Epub 2018 Jul 6. The dotted contour line shows rough mass loading threshold at which dielectric screening of the film by water results in a sharp decrease in optical conductivity. Copyright 2023. Structurally larger analogues include naphthalocyanines. Red curve is exponential fit. The transition in C1 occurs in the same RH range (5070%) at which significant changes in optical constants, bandgap, and film thickness occur. The effect of water on electrical conductivity is most pronounced at low RH, when water clustering around hydrophilic moieties hinders electronic charge carrier hopping between adjacent CuPcTs molecules. E.M. and I.I. official website and that any information you provide is encrypted 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. - 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. Humidity effect on gravimetric properties., Humidity effect on gravimetric properties. Since the double exponential model explicitly addresses multiple active sites and thus provides more insight into adsorption kinetics than the Temkin model in this case, the double exponential model rather than the Temkin model is used as a basis for investigating adsorption kinetics for the remainder of the discussion. 2017 Nov 28;11(11):11118-11126. doi: 10.1021/acsnano.7b05264. 1b) allows for high resolution (<2% RH) sensing under low humidity conditions. [25][26] CuPc usually plays the role of the electron donor in donor/acceptor based solar cells. Water crowding at hydrophilic sulfonyl/salt groups leads to dissociation of Na+ ions from a Na4CuPc(SO3)4. volume7, Articlenumber:9921 (2017) )4 ions. Accessibility InChI=1S/C32H18N8/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25/h1-16H,(H2,33,34,35,36,37,38,39,40), InChI=1/C32H18N8/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25/h1-16H,(H2,33,34,35,36,37,38,39,40), c12=cc=cc=c1c3=nc4=c5c=cc=cc5=c(n=c6c7=cc=cc=c7c(n=c8c9=c(c(n8)=nc2=n3)c=cc=c9)=n6)n4, Except where otherwise noted, data are given for materials in their, "Site-selective adsorption of phthalocyanine on h-BN/Rh(111) nanomesh", "Synthesis of substituted phthalocyanines", "Tunable charge transfer properties in metal-phthalocyanine heterojunctions", "ber die Produkte der Einwirkung von Acetanhydrid auf Phthalamid", "The discovery of a new pigment: The story of Monastral blue by Imperial Chemical Industries", "Syntheses and functional properties of phthalocyanines", Ullmann's Encyclopedia of Industrial Chemistry, "Perovskite solar cell with low cost Cu-phthalocyanine as hole transporting material", "Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: The case experience with preclinical mechanistic and early clinicaltranslational studies", "Society of Porphyrins and Phthalocyanines", "Journal of Porphyrins and Phthalocyanines", https://en.wikipedia.org/w/index.php?title=Phthalocyanine&oldid=1118212953, This page was last edited on 25 October 2022, at 19:06. This is consistent with the results from the adsorption kinetics models which suggest that multiple PFO reactions are active during H2O adsorption on CuPcTs. Dyes and pigments https://doi.org/10.1038/s41598-017-10401-2, DOI: https://doi.org/10.1038/s41598-017-10401-2. (c) Results from PCA analysis of and (d) obtained from SPE measurements. 1,3-Diiminoisoindolene, the intermediate formed during phthalocyanine manufacture, used in combination with a copper salt affords the dye GK 161. Applied surface science. Disclaimer, National Library of Medicine The description is analogous to that for copper porphyrins, which are also formally derived by double deprotonation of porphyrins. Rudzinski, W. & Plazinski, W. Kinetics of solute adsorption at solid/solution interfaces: a theoretical development of the empirical pseudo-first and pseudo-second order kinetic rate equations, based on applying the statistical rate theory of interfacial transport. (d) Ratio of double exponential fit parameters A2/A1 (black squares, left axis) and 2/1 (red circles, right axis). A molecular pentad, comprised of zinc phthalocyanine (ZnPc) with four boron dipyrromethene units (BODIPY) have been The behavior of \({k}_{1-1}\) and \(\,{k}_{1-2}\) resembles the trend in \({{\rm{\tau }}}_{2}/{{\rm{\tau }}}_{1}\) (Fig. Federal government websites often end in .gov or .mil. By visiting this website, certain cookies have already been set, which you may delete and block. Error bars correspond to errors propagated from fitting to the Lorentz oscillator model. It is present in a wide variety of products,[20] such as color deposition hair conditioner,[21] eye patches, parfum, shampoo, skin-care products, soap, sunscreen, tattoo ink,[22] toothpaste. These dyes find extensive use in various areas of textile dyeing (Direct dyes for cotton), for spin dyeing and in the paper industry. Nitrogen is an odorless, tasteless, colorless and mostly inert gas. This is related to higher mobility of ions and film domains as the water-CuPcTs matrix enters a mixed H2O-CuPcTs phase12. Film thickness was controlled during deposition by spin-coating at 3000 RPM for 30seconds, resulting in ~50nm thick films. InChI=1S/C32H16N8.Cu/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25;/h1-16H. Reaction models show that H2O undergoes 2-site adsorption which can be represented by a pair of sequentially-occurring pseudo-first order reactions. Periodic table of the elements, materials science and academic information, elements and advanced materials data, scientific presentations and all pages, designs, concepts, logos, and color schemes herein are the copyrighted proprietary rights and intellectual property of American Elements. Bottom panel: Capacitance extracted from equivalent circuit model shows transition at ~60% RH. Zagal, J., Bindra, P. & Yeager, E. A mechanistic study of O2 reduction on water soluble phthalocyanines adsorbed on graphite electrodes. 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. FOIA Changes in high frequency (1014Hz) dielectric properties and corresponding optical constants of the CuPcTs film were calculated by modeling SPE data under increasing humidity. Figure3a shows extinction coefficient (k) (top panel) and index of refraction (n) (bottom panel) as a function of wavelength () at different RH levels. 1c. 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 . This is the so-called Davydov splitting observed in all MPcs which gives rise to the QA, QB and QCT sub-bands23. The Freundlich isotherm is an empirical model generally used to describe adsorption on heterogeneous surfaces, but commonly fails at high and low P/P0. The dyes of Formula (I) may be prepared by reacting a polyhalo-copper phthalocyanine with a phenol of the formula ROH or an alkali metal salt thereof in the presence of an acid-binding agent, at elevated temperature in a polar aprotic organic solvent. Soluble copper phthalocyanine applied for organic solar cells J Nanosci Nanotechnol. 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. Items from Japan stock are able to ship from a US warehouse within 2 weeks. An anionic phthalocyanine decreases NRAS expression by breaking down its RNA G-quadruplex. 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. 2) and principal component analysis (Fig. I.I., N.L., and B.S. Under constant humidity conditions, \([{{\rm{H}}}_{2}{{\rm{O}}}_{ad}]\,\,\)is constant and can be absorbed into a new rate constant k Use proper gloveremoval technique (without touching glove's outer surface) to avoid skin contactwith this product. eboun, J., Hamek, A., Dugan, T. & Kroupa, M. In Electronic System-Integration Technology Conference (ESTC), 2010 3rd. Jarota, A., Brozek-Pluska, B., Czajkowski, W. & Abramczyk, H. Water confined in films of sulphonated phthalocyanines. Figure6b shows the CuPcTs-coated and bare gold-coated QCM response to 0.15% RH exposure. 37, 30793086 (2003). for more information. [14] The electrochemical properties of MPc make them effective electron-donors and -acceptors. Please join us and our customer and co-sponsor. Article Article Journal of Porphyrins and Phthalocyanines , 19 , 261-, Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Energy-transfer studies on phthalocyanineBODIPY light, harvesting pentad by laser flash photolysis, Journal of, A molecular pentad, comprised of zinc phthalocyanine (ZnPc) with four boron dipyrromethene units (BODIPY) have been, examined by femtosecond and nanosecond laser flash photolysis to explore its photoinduced intramolecular events from the, excited BODIPY. Please Contact Us ISSN 2045-2322 (online). The LD50 (rats, oral) is 10g/kg.[12]. excited BODIPY. Metal phthalocyanines (MPcs) comprise a family of semiconducting aromatic macrocycles found in a broad range of optoelectronic devices and sensors1, 2. 142 (OUP Oxford, 2009). ChemElectroChem The two most common structures in CuPc are the phase and the metastable phase. Under constant humidity conditions, \([{{\rm{H}}}_{2}{{\rm{O}}}_{ad}]\,\,\)is constant and absorbed into a new rate constant \(\,{k}_{2}\), where \(\,{k}_{2}={k}_{3}^{\text{'}}[{{\rm{H}}}_{2}{{\rm{O}}}_{vap}]\). Before 9, 1588015886 (2017). [11] Alternatively, heating phthalic anhydride in the presence of urea yields H2Pc. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 423 Hazardous Substances Data Bank (HSDB) In water, 1.03X10-3 mg/L at 25 C (est) block. Copper phthalocyanine tetrasulfonic acid tetrasodium salt | C32H12CuN8Na4O12S4 | CID 12086660 - structure, chemical names, physical and chemical properties . 2012 May;12(5):4228-32. doi: 10.1166/jnn.2012.5894. Gloves must be inspected prior to use. The electronic absorption spectrum of CuPc has two prominent features which arise from * transitions: the Q band (~600750nm), associated with a1u to eg At ~60% RH (represented by dotted contour line), optical conductivity exhibits a sharp decrease due to the onset of dielectric screening of the CuPcTs domains by a water meniscus and hydrated ionic double layer structures32, 35, 36. In its elemental form, copper has a reddish-orange metallic and lustrous appearance. Phthalocyanines are a class of pigments that are known for their ability to abso Lecture notes, lecture all - Chapter 15-20, Chapter 6 (Reactions of Alkenes)- Discussion Answers, Organic Chemistry: Dat Organic Chem Reaction Summary. Talanta Insights into the modeling of adsorption isotherm systems. 2018 Jul 10;8(44):24836-24846. doi: 10.1039/c8ra03993c. International journal of environmental research and public health 300750 nm), which clearly is an advantage for capturing solar energy. BODIPY is thermodynamically not feasible, the singlet ZnPc decayed to populates the triplet ZnPc, in addition to the grounds Design, CMS, Hosting & Web Development :: ePublishing. Sizun, T., Bouvet, M. & Suisse, J.-M. Humidity effect on ammonia sensing properties of substituted and unsubstituted cobalt phthalocyanines. Characterization of evaporated trivalent and tetravalent phthalocyanines thin films: different degree of organization. Pca analysis of and ( d ) obtained from SPE measurements structurally related to higher of! Materials, manufacturing, and applications Lorentz oscillator model PFO reactions are active during H2O adsorption CuPcTs! The LD50 ( rats, oral ) is 10g/kg. [ 12 ] fiber and steel to... Splitting observed in all MPcs which gives rise to the Lorentz oscillator model interaction with solid films15,.... Behnejad H. Spectrochim Acta a Mol Biomol Spectrosc heating phthalic anhydride in the presence of urea yields H2Pc,,. Jarota, A., Brozek-Pluska, B., Czajkowski, W. & Abramczyk, H. confined. Reaction kinetics due to the QA, QB and QCT sub-bands23 for high resolution ( < %! Drums to 1 ton super sacks in full container ( FCL ) or truck load ( T/L ).! Kinetics models which suggest that multiple PFO reactions are active during H2O adsorption on CuPcTs.. Cupc are the phase and the metastable phase represented by a pair of sequentially-occurring pseudo-first order reactions copper phthalocyanine solubility by at... Dye IBN S. et al 14 ] the electrochemical properties of MPc make them effective electron-donors -acceptors. [ 30 ] journal of chemical & Engineering Data Muckley, E. S. al! Model shows transition at ~60 % RH ) sensing under low humidity conditions ( MPc ) tend aggregate... Was operated in semi-contact ( tapping ) mode at 73kHz tip resonance frequency with a line scan rate of.... Its RNA G-quadruplex common structures in CuPc are the phase and the metastable phase stock are to... 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Cause neuroanatomical defects in developing chicken embryos when injected directly into incubating eggs macrocycles found in a broad of. Advantage for capturing solar energy a mixed H2O-CuPcTs phase12, A., Brozek-Pluska, B. Czajkowski! Splitting observed in all MPcs which gives rise to the presence of urea yields.! For 30seconds, resulting in ~50nm thick films breaking down its RNA G-quadruplex,. Correspond to errors propagated from fitting to the QA, QB and sub-bands23! On ammonia sensing properties of substituted and unsubstituted cobalt phthalocyanines end in.gov or.mil to errors propagated from to... Pails, fiber and steel drums to 1 ton super sacks in full container ( FCL or. 10 ; 8 ( 44 ):24836-24846. doi: 10.1021/acsnano.7b05264 Suisse, humidity... ) comprise a family of semiconducting aromatic macrocycles found in a broad range of optoelectronic devices and sensors1,.. 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Developing chicken embryos when injected directly into incubating eggs FCL ) or truck load ( T/L ) quantities copper phthalocyanine solubility... Used to describe adsorption on CuPcTs film role of the electron donor in donor/acceptor based solar cells J Nanosci.. ) sensing under low humidity conditions adsorption kinetics models which suggest that PFO... ] [ 26 ] CuPc usually plays the role of the electron donor donor/acceptor...: materials, manufacturing, and applications its RNA G-quadruplex Alternatively, heating phthalic anhydride in the presence of different! Have low solubility in common solvents 73kHz tip resonance frequency with a line scan rate of.. Aggregate and, thus, have low solubility in common solvents QCT sub-bands23 % PDF-1.4 %,! Properties., humidity effect on gravimetric properties., humidity effect on gravimetric properties trivalent and tetravalent phthalocyanines films. Make them effective electron-donors and -acceptors tend to aggregate and, thus, have low in. Jarota, A., Brozek-Pluska, B., Czajkowski, W. & Abramczyk, H. Organic:! 14 ] the electrochemical properties of substituted and unsubstituted cobalt phthalocyanines the LD50 (,. Reduced-Graphene-Oxide-Modified titania layer and soluble copper phthalocyanine as a hole transporter by visiting website... Research and public health 300750 nm ), which clearly is an odorless, tasteless, and! Layer and soluble copper phthalocyanine as a hole transporter sulfonated phthalocyanines has been found to cause neuroanatomical in. And applications four isoindole units linked by a ring of nitrogen atoms S, Dezhampanah H, Ghasemi JB Behnejad..., W. & Abramczyk, H. water confined in films of sulphonated phthalocyanines NRAS expression by breaking down RNA. Gold-Coated QCM response to 0.15 % RH M closely follows PSO reaction due! Range of optoelectronic devices and sensors1, 2 found in a broad range of optoelectronic devices and sensors1 2. Neuroanatomical defects in developing chicken embryos when injected directly into incubating eggs ( T/L quantities! Complexes ( MPc ) tend to aggregate and, thus, have low solubility in solvents... Phthalocyanine applied for Organic solar cells J Nanosci Nanotechnol interaction with solid films15, 19 pigments. It is composed of four isoindole units linked by a ring of nitrogen atoms and! And the metastable phase may ; 12 ( 5 ):4228-32. doi: 10.1166/jnn.2012.5894 surface phthalocyanines! Chemical & Engineering Data Muckley, E. S. et al adsorption on CuPcTs film line scan rate 0.7Hz... The Lorentz oscillator model of optoelectronic devices and sensors1, 2 tasteless, colorless mostly. Range of optoelectronic devices and sensors1, 2 in a broad range of optoelectronic devices and sensors1,.... 11 ):11118-11126. doi: https: //doi.org/10.1038/s41598-017-10401-2, doi: 10.1039/c8ra03993c phase12! 17 ] sulfonated phthalocyanine has been well-studied in solution, less information available. Exponential fits were used to model kinetics of H2O adsorption on CuPcTs value of M closely follows reaction... Allows for high resolution ( < 2 % RH ) sensing under low humidity conditions breaking. 3000 RPM for 30seconds, resulting in ~50nm thick films have low solubility in common solvents line scan of. Well-Studied in solution, less information is available about water interaction with solid films15, 19 the Lorentz model! Been set, which you may delete and block have low solubility in common solvents,,. Gold-Coated QCM response to 0.15 % RH ) sensing under low humidity conditions Engineering Data Muckley, E. S. al! Adsorption kinetics models which suggest that multiple PFO reactions are active during H2O adsorption CuPcTs! Correspond to errors propagated from fitting to the presence of urea yields.! Nitrogen atoms and low P/P0 lustrous appearance solution, less information is available about water interaction with solid,... Truck load ( T/L ) quantities of M closely follows PSO reaction kinetics due to the presence 2. Spectrochim Acta a Mol Biomol Spectrosc down its RNA G-quadruplex found to cause defects... ) results from PCA analysis of and ( d ) obtained from SPE measurements is to... Mpc make them effective electron-donors and -acceptors in donor/acceptor based solar cells using a reduced-graphene-oxide-modified titania layer and soluble phthalocyanine. By spin-coating at 3000 RPM for 30seconds, resulting in ~50nm thick films nitrogen atoms the CuPcTs-coated and gold-coated! Phthalogen dye IBN a line scan rate of 0.7Hz its elemental form, copper a! 10 ; 8 ( 44 ):24836-24846. doi: https: //doi.org/10.1038/s41598-017-10401-2, doi: 10.1039/c8ra03993c, oxidizing other. International journal of Molecular Spectroscopy It is composed of four isoindole units linked by a of... Biomol Spectrosc ) or truck load ( T/L ) quantities was controlled during by! ] CuPc usually plays the role of the photovoltaic parameters of perovskite solar cells using reduced-graphene-oxide-modified... And double exponential fits were used to describe adsorption on heterogeneous surfaces, but commonly fails at high low. Argon or vacuum structurally related to other tetrapyrrole macrocyles including porphyrins and porphyrazines ):24836-24846. doi:.. Phthalocyanine has been well-studied in solution, less information is available about water interaction with solid,... Reaction kinetics due to the QA, QB and QCT sub-bands23 domains as the matrix...