19333-10-9

Usage

Uses

Precursor to stacked-ring silicon phthalocyanines.

InChI:InChI=1/C32H16Cl2N8Si/c33-43(34)41-29-21-13-5-6-14-22(21)31(41)39-27-19-11-3-4-12-20(19)28(36-27)40-32-24-16-8-7-15-23(24)30(42(32)43)38-26-18-10-2-1-9-17(18)25(35-26)37-29/h1-16H/b37-25-,37-29-,38-26-,38-30-,39-27-,39-31-,40-28-,40-32-

Upstream product

• 160956-25-2 isoindole-1,3-diylidenediamine 
• 10026-04-7 tetrachlorosilane 
• 685898-11-7 C₁₉H₂₁N₃O₃ 
• 91-15-6 phthalonitrile 

Relevant academic research and scientific papers

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.

Silicon Phthalocyanines Axially Disubstituted with Erlotinib toward Small-Molecular-Target-Based Photodynamic Therapy

Small-molecular-target-based photodynamic therapy—a promising targeted anticancer strategy—was developed by conjugating zinc(II) phthalocyanine with a small-molecular-target-based anticancer drug. To prevent self-aggregation and avoid problems of phthalocyanine isomerization, two silicon phthalocyanines di-substituted axially with erlotinib have been synthesized and fully characterized. These conjugates are present in monomeric form in various solvents as well as culture media. Cell-based experiments showed that these conjugates localize in lysosomes and mitochondria, while maintaining high photodynamic activities (IC50 values as low as 8 nm under a light dose of 1.5 J cm?2). With erlotinib as the targeting moiety, two conjugates were found to exhibit high specificity for EGFR-overexpressing cancer cells. Various poly(ethylene glycol) (PEG) linker lengths were shown to have an effect on the photophysical/photochemical properties and on in vitro phototoxicity.

Photoactive Surface-Grafted Polymer Brushes with Phthalocyanine Bridging Groups as an Advanced Architecture for Light-Harvesting

Surface-grafted polymer brushes of novel ladder-like architecture were proposed for inducing ordering of chromophores embedded therein. The brushes with acetylene side groups were obtained by surface-initiated photoiniferter-mediated polymerization. The acetylene moieties reacted then through a “click” process with an axially azide-bifunctionalized silicon phthalocyanine bridging the neighboring chains that inherently adopt extended conformations in dense brushes. FTIR, quartz crystal microbalance, and atomic force microscopy were used to study formation and structure of the photoactive brushes varying in grafting densities. Importantly, photophysical properties of the chromophores were virtually unaffected upon embedding them into the brushes, as evidenced by UV/Vis absorption and emission spectroscopy. Owing to the unique ordering of the chromophores, the proposed method may open new opportunities for the fabrication of light-harvesting systems suitable for photovoltaic or sensing applications.

Synthesis and characterization of phthalocyaninatosilicon with bridging ligands (L) (L = Dimethylsilane, diphenylsilane, methylphenylsilane)

Several new types of cofacial compounds of μ-(dimethylsilane)phthalocyaninatosilicon [PcSi(dms)]n, μ-(diphenyl-silane)phthalocyaninatosilicon [PcSi(dps)]n, and μ-(methylphenylsilane)phthalocyaninatosilicon [PcSi(mps)]n were synthesized by the reaction of dichlorophthalocyaninatosilicon (PcSiCl2) with dichlorodimethylsilane, dichlorodiphenylsilane, and dichloromethylphenylsilane in xylene, respectively. The corresponding silane-bridged phthalocyaninatosilicon compounds were characterized by Fourier transform infrared (FT-IR), 29Si-NMR, UV-vis, elemental analysis, and thermogravimetry/differential thermal analysis (TG/DTA). The electrical conductivities of the compounds were measured by the four-probe method, and the bridged phthalocyaninatosilicon compounds without the dopant showed very low electrical conductivity. A clear increase in conductivity, however, was observed for the doped compounds [PcSi(L)Iy]n and [PcSi(L) (ClO4)y]n, which was found to be in the range σRT = 10-6-10-3 S/cm with doping (I2, AgClO4).

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.

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.

Preparation method of di-(4-dibenzothiophene-2-phenoxy) axially substituted silicon phthalocyanine

The invention belongs to a preparation method of a di-(4-dibenzothiophene-2-phenoxy) axially substituted silicon phthalocyanine complex. The complex is used as a photosensitizer for antibacterial treatment. The preparation method comprises the following steps: (1) adding 2-bromodibenzothiophene, 4-hydroxyphenylboronic acid, 1, 3-dibromopropane and tetrakis(triphenylphosphine) palladium into a mixed solution of tetrahydrofuran and anhydrous K2CO3, stirring and mixing, and refluxing to prepare a precursor 4-dibenzothiophene-2-phenol, and (2) adding the precursor 4-dibenzothiophene-2-phenol and dichlorosilane (IV) phthalocyanine into a toluene solution in the presence of anhydrous K2CO3, stirring and mixing at 140 DEG C, and refluxing to prepare the di-(4-dibenzothiophene-2-phenoxy) substituted silicon phthalocyanine. According to the silicon phthalocyanine prepared by the invention, the steric hindrance of an aryl thiophene structure is utilized to inhibit the formation of phthalocyanineaggregate, and benzothiophene is introduced to the axial position of phthalocyanine, so that the silicon phthalocyanine has antimicrobial and anticancer effects and can be applied to photosensitizers.

Water-soluble mitochondrial targeting ethoxy-bromopropyl imidazole axial substituted silicon phthalocyanine and preparation method and application thereof

The invention discloses a water-soluble mitochondrial targeting ethoxy-bromopropyl imidazole axial substituted silicon phthalocyanine and a preparation method and application thereof. The invention relates to a water-soluble mitochondrial targeting di - (1 - (2 - ethoxy) -3 - (3 - bromopropyl) imidazole) axial substituted silicon phthalocyanine and a preparation method and application thereof. The invention adopts 1 - (2 - hydroxyethyl) -3 - (3 - bromopropyl) imidazole and dichlorosilane (IV) phthalocyanine to prepare di - (1 - (2 - ethoxy) -3 - (3 - bromopropyl) imidazole) axial substituted silicon phthalocyanine. .

Matryoshka doll-type gold nanorod composite system loaded with novel sulfydryl N-heterocyclic silicon (IV) phthalocyanine complex

The invention discloses a Matryoshka doll-type nano gold rod system loaded with di-(1-(4-hydroxyphenyl)-5-sulfydryl-tetrazolyl) silicon phthalocyanine as well as a preparation method and an application thereof. The preparation method comprises the following steps: firstly synthesizing a gold nanorod, then coating the surface of the gold nanorod with aminated silicon dioxide, and finally coating the surface of the gold nanorod with aminated silicon dioxide with a layer of gold nanospheres to prepare the Matryoshka doll-type gold nanorod with a three-layer cavity structure, enabling dichlorosilane phthalocyanine to react with 1-(4-hydroxyphenyl)-5-sulfydryl-tetrazole to synthesize di-(1-(4-hydroxyphenyl)-5-sulfydryl-tetrazole) silicon(IV)phthalocyanine; and finally, preparing a Matryoshka doll-type gold nanorod system loaded with di-(1-(4-hydroxyphenyl)-5-sulfydryl-tetrazolyl)silicon(IV)phthalocyanine and Matryoshka doll-type gold nanorods through a molecular assembly method, and takingthe Matryoshka doll-type gold nanorod system as photodynamic and photothermal therapy combined inactivation drug-resistant bacteria and tumors.

Prop-2-ynyloxybenzyloxy substituted phthalocyanine-based polymeric nanoparticles: synthesis, photophysical properties and in?vitro PDT efficacy

Two prop-2-ynyloxybenzyloxy axially/peripherally substituted zinc/silicon phthalocyanines (YSiPc and YZnPc) were synthesized. They were encapsulated into an amphiphilic block copolymeric micelle polyethylene glycol monomethyl ether-polycaprolactone (MPEG5000–PCL2000) to form polymeric nanoparticles YSiPc@MPEG5000–PCL2000 and YZnPc@MPEG5000–PCL2000. The photophysical and photochemical properties of these polymeric nanoparticles were studied by UV/Vis and fluorescence spectroscopy. The cellular uptake and reactive oxygen species (ROS) production abilities of two polymeric nanoparticles in MCF-7 breast cancer cells were evaluated by confocal laser scanning imaging. YSiPc@MPEG5000–PCL2000 exhibited a higher cellular uptake, higher ROS generation ability as well as higher photodynamic efficacy against MCF-7 cells. YSiPc@MPEG5000–PCL2000 is a promising photosensitizer for photodynamic therapy.