19333-15-4

Usage

Uses

Used in Electronics Industry:
Silicon dihydroxyl phthalocyanine is used as a component in the development of organic semiconductors and photovoltaic devices due to its enhanced light-absorbing properties, which contribute to improved performance and efficiency in electronic devices.
Used in Photodynamic Therapy for Cancer Treatment:
Silicon dihydroxyl phthalocyanine is used as a photosensitizer in photodynamic therapy for cancer treatment. Its unique chemical structure allows it to absorb light and generate reactive oxygen species, which can selectively destroy cancer cells while minimizing damage to healthy tissues.
Used in Dye-Sensitized Solar Cells:
Silicon dihydroxyl phthalocyanine is used as a sensitizer in dye-sensitized solar cells. Its light-absorbing properties enable efficient conversion of sunlight into electricity, contributing to the development of more efficient and sustainable energy solutions.

Upstream product

• 160956-25-2 isoindole-1,3-diylidenediamine 
• 10026-04-7 tetrachlorosilane 
• 7732-18-5 water 
• 1310-73-2 sodium hydroxide 
• 19333-10-9 phthalocyanine silicon(IV) dichloride 
• 19333-10-9 silicon(IV) phthalocyanine dichloride 

Downstream Products

• 886982-96-3 C₄₂H₄₄N₁₀O₂Si₃ 
• 1421834-65-2 {bis-[bis-(p-N,N-dimethylaminophenyl)]-3-(piperidine-1-yl)propylsilyloxy} silicon(IV) phthalocyanine 
• 1421834-79-8 {bis-[3-(m-N,N-dimethylaminophenyloxy)propyl-dipropylsilyloxyl]}silicon(IV) phthalocyanine 
• 1421834-71-0 {bis-[bis-(p-N,N-dimethylaminophenyl)]propylsilyloxyl} silicon(IV) phthalocyanine 
• 92396-89-9 bis(tri-n-hexylsilyl oxide) silicon phthalocyanine 

Relevant academic research and scientific papers

A Galactose Dendritic Silicon (IV) Phthalocyanine as a Photosensitizing Agent in Cancer Photodynamic Therapy

Two protected galacto-dendritic units have been axially coordinated to the central ion of a silicon(IV) phthalocyanine to afford SiPcPGal4 containing four units of galactose per macrocycle. These biological moieties provided better solubility in aqueous medium and a sensitizer with higher absorption peaks at 680–690 nm. The photodynamic activity of SiPcPGal4 was evaluated against UM-UC-3 human bladder cancer cell line and the results were compared with the activity of the reported SiPcPGal2 and SiPc(OH)2. SiPcPGal4 had a better uptake and it was a better toxicity inducer than SiPcPGal2 and SiPc(OH)2 owing to its four galactose units, protected by isopropylidene groups, which can act as targeted micelles.

Theoretical and Experimental Studies on the Near-Infrared Photoreaction Mechanism of a Silicon Phthalocyanine Photoimmunotherapy Dye: Photoinduced Hydrolysis by Radical Anion Generation

Ligand release from IR700, a silicon phthalocyanine dye used in near-infrared (NIR) photoimmunotherapy, initiates cancer cell death after NIR absorption, although its photochemical mechanism has remained unclear. This theoretical study reveals that the direct Si-ligand dissociation by NIR light is difficult to activate because of the high dissociation energy even in excited states, i. e., >1.30 eV. Instead, irradiation generates the IR700 radical anion, leading to acid-base reactions with nearby water molecules (i. e., calculated pKb for the radical anion is 7.7) to produce hydrophobic ligand-released dyes. This suggests two possibilities: (1) water molecules participate in ligand release and (2) light is not required for Si–ligand dissociation as formation of the IR700 radical anion is sufficient. Experimental evidence confirmed possibility (1) by using 18O-labeled water as the solvent, while (2) is supported by the pH dependence of ligand exchange, providing a complete description of the Si-ligand bond dissociation mechanism.

POLYMERIC MICELLE –PHTHALOCYANINE NANO-SYSTEMS FOR PHOTODYNAMIC THERAPY AND/OR FLUORESCENCE-BASED IMAGING

Polymeric micelle - phthalocyanine nano-systems are useful as therapeutic, diagnostic, and theranostic (therapeutic and diagnostic) nano-systems for photodynamic therapy and/or fluorescence-based imaging. In particular, there is provided a composition comprising polymeric micelles as a nanocarrier and one or more molecules of a phthalocyanine as a payload, wherein the phthalocyanine is of the formula (I) in which R1-R8 and Ra and Rb are as defined. The invention also provides certain groups of phthalocyanines of general formula (I) that are also novel.

Bis(tri-n-alkylsilyl oxide) silicon phthalocyanines: A start to establishing a structure property relationship as both ternary additives and non-fullerene electron acceptors in bulk heterojunction organic photovoltaic devices

Previous studies have shown that the use of bis(tri-n-hexylsilyl oxide) silicon phthalocyanine ((3HS)2-SiPc) as a solid ternary electroactive additive in poly(3-hexylthiophene):phenyl-C61-butyric acid methyl ester P3HT:PC61BM bulk heterojunction organic photovoltaic (BHJ OPV) devices resulted in an increased performance. It has been hypothesized that the increase in efficiency is partially due to the unique and odd combination of high solubility and strong driving force of crystallization previously observed for (3HS)2-SiPc. In this follow-up study, two chemical variants of (3HS)2-SiPc, namely bis(tri-n-butylsilyl oxide) ((3BS)2-SiPc) and bis(tri-n-isopropylsilyl oxide) ((3TS)2-SiPc) were synthesized to determine how small changes in the chemical structure would affect the properties of the material and its performance within BHJ OPV devices. We observed that the use of either (3XS)2-SiPc compound results in a further ～10% increase in JSC compared to the use of (3HS)2-SiPc. We also did a preliminary assessment of the use of three (3XS)2-SiPcs as replacements for PC61BM in straight binary P3HT-based BHJ OPV devices. Despite achieving only ～1% PCE efficiencies, observations including a ≈50% increase in VOC over a P3HT:PC61BM baseline and a decent fill factor indicate to us that (3XS)2-SiPcs do have potential as non-fullerene acceptors and advantageous alternatives due to their low embedded energy and therefore their inherent sustainability. X-ray diffraction of ternary and binary BHJ devices demonstrates that both (3BS)2-SiPc and (3TS)2-SiPc experienced similar increase in crystallite density (d-spacing) relative to (3HS)2-SiPc which we surmise plays a role in the improved device efficiency. Like (3HS)2-SiPc, for these two new additives, we also observed a high tendency of crystallization. The results from this study suggest that solubility and driving force to crystallize are important factors in determining the extent to which an additive will migrate to the donor/acceptor interface and thus affect its performance as a ternary additive in BHJ OPV devices. Based on the three (3XS)2-SiPcs used in this study, the smaller tri-n-alkylsilyl oxide molecular fragments seem to work better. Therefore, moving forward, we will continue to consider smaller molecular fragments that still enable solubility and processability of (3XS)2-SiPcs.

Production process for colorant, colorant composition, toner, ink for ink jet recording and color filter

Provided is a production process for a colorant which contains a silicon phthalocyanine compound making it possible to reach a targeted particle diameter even by a conventional dispersing method and which is excellent in performances such as a color reproducibility, a light fastness, an electrostatic property, a transparency and the like, and a colorant composition, a toner, an ink for ink jet recording and a color filter which are excellent in the above performances. The above production process is a production process for a colorant containing a silicon phthalocyanine compound and a copper phthalocyanine compound and is characterized by having a preparing step of reacting raw materials of a silicon compound and phthalocyanine under the presence of a copper salt or the copper phthalocyanine compound described above to prepare the silicon phthalocyanine compound described above.

Phthalocyanine dyes

Fluorescent dyes are disclosed which are useful as reporter groups for labeling biomolecules. The silicon phthalocyanine dyes disclosed are preferably water soluble, isomericly pure, possess high quantum yield, and are useful in bioassays.

Ab-initio X-ray powder structure analysis of two polymorphs of dihydroxysilicon phthalocyanine

This paper reports on the synthesis and ab-initio X-ray powder structure determination of two polymorphs of [Si(OH)2Pc], where Pc = phtalocyaninato. We found that one of the polymorphs (Phase II) shows high sensitivity for an electrophotographic photoreceptor, but that the other (Phase I) doesn't have photosensitivity. The difference in the sensitivity depends on only the crystal structures. This material has not been able to be grown to a single crystal with sufficient size for single crystal X-ray analysis, but it is very important to determine the crystal structures of the two polymorphs for understanding the mechanism of the performance of the electrophotographic photoreceptor. In this work we carried out ab-initio X-ray powder structure analysis. The compound crystallizes in space group P1 (Phase I), Z = 1 with unit-cell parameters of a = 12.992(1), b = 7.2830(8), c = 6.861(1) A, α = 104.413(7)°, β = 101.757(8)°, γ = 96.973(6)°and in space group P21/n (Phase II), Z = 2 with unit-cell parameters of a = 12.7494(5), b = 14.5778(6), c = 6.7727(3) A, β = 94.353(2)°. Both phases have symmetry center in the molecules (on Si atom) and intermolecular hydrogen bonds (O-H ··· N). These hydrogen bond modes of Phase I and Phase II are the same. The main difference in packings was revealed between the crystals: Phase II crystal has the herringbone structure, while in Phase I all molecules form the parallel stack columns.

Synthesis and chemical properties of (PcSi)(AlCl4)2 (Pc = phthalocyanine macrocycle). The first friedel-crafts silylation reaction

(PcSi)(AlCl4,)2, synthesized by the reaction of PcSiCl2 with AlCl3, underwent electrophilic substitution with anthracene to afford PcSi (C14H10)2.

Synthesis, structural and conformational analysis and chemical properties of phthalocyaninatometal complexes

Syntheses of the phthalocyaninatometal complexes were performed and the crystal and molecular structures were determined by single-crystal X-ray diffraction analysis. The general formulas of these Pc dye compounds are -[Si(Pc)OSiR2/1R2SiR2/1O](n)-and Si(Pc)(OSiR1R2R3)2: -[Si(Pc)OSi(CH3)2(CH2)7Si(CH3)2O](n)- (1), Si(Pc)[OSi(C6H13)3]2 (2) Si(Pc)[OSiC8H17(CH3)2]2 (3) and Si(Pc)[OSiCH3C12H25CH3]2 (4). These Pc dye derivatives were prepared by refluxing a mixture of Si(Pc)(OH)2 and SiR1R2R3Cl in pyridine, followed by cooling the mixture slowly and then drying the resulting precipitates. For 1-3, the Pc skeleton and the oxo-bridged substituentes are coplanar. The dihedral angle between the mean planes of the Pc skeleton and two single-atom Si(me) [Si(me)-O-Si(pc)-O-Si(me)] is nearly at right angles. The Si(pc)-O bonds are shorter than the Si(pc)-N bonds and the Si(me)-O bonds are shorter than the Si(pc)-O bonds. For 1, the Pc microcyclic rings are related by a center of symmetry at the center of the O1-Si1-O2 bonds. The chemical formula of a mononer is C43H42N8O2Si3 (C25H28N5O2Si3 in crystallographic symmetry) and the polymer is built up by the addition polymerization of the monomers. The polymer chain is constructed at the siloxy group along the a axis. Two hexyl groups of two siloxy side groups for 2 have the same direction, but one hexyl extends in the opposite direction. For 3, two methyl groups and one octyl group extend in the opposite direction. We applied Pc dyes 2-4, mixed with a polymer for the control of the aggregation state to CD-R and DVD-R recording systems. The aggregation state of the recording layer is controlled by choosing the set of axial substituents R1-R3. The interactions of Pc dyes with polymers are dependant upon the length of axial substituents. We achieved the best writing contrast and the highest stability with the mixed PC dye 4. The conformation of axial substituents is very important for the ability of the dye aggregation and the capability to control the aggregation state.

Electrophilic cleavage reactions of carbon-silicon bonds in neutral hexacoordinate silicon compounds: diorgano(phtalocyaninato)silicon

Preparations of diorgano(phtalocyaninato)silicon 1)(R2)> and their reactions with N-bromosuccinimide (NBS), halogens, copper(II) halides, and 3-chloroperbenzoic acid (MCPBA) are reported.The alkyl-silicon bonds are readily cleaved by NBS, halogens, and CuX2 to give the corresponding alkyl halides.The reactivity of aryl-silicon bonds toward NBS and halogen depends greatly on the electronic effect of the substituent on the benzene ring, but these bonds are almost inert to CuX2.The reactivity of the carbon-silicon bond towards NBS cleavage decreases in the order 4-MeOC6H4 > n-C8H17 > 4-MeC6H4 > Ph >> 3-CF3C6H4.Cleavage of alkyl-silicon bonds may involv one-electron transfer from substrate to reagent and alkyl radical intermediates, while the electrophilic aromatic substitution mechanism may operate in the cleavage of aryl-silicon bonds. are stable to MCPBA.