19333-10-9Relevant articles and documents
Synthesis, structural and conformational analysis and chemical properties of phthalocyaninatometal complexes
Sasa, Noboru,Okada, Kenji,Nakamura, Kazuo,Okada, Sachiko
, p. 163 - 178 (1998)
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.
Photoactive Surface-Grafted Polymer Brushes with Phthalocyanine Bridging Groups as an Advanced Architecture for Light-Harvesting
Szuwarzyński, Micha?,Wolski, Karol,Pomorska, Agata,Uchacz, Tomasz,Gut, Arkadiusz,?apok, ?ukasz,Zapotoczny, Szczepan
, p. 11239 - 11243 (2017)
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.
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
Dang, Minh-Trung,Grant, Trevor M.,Yan, Han,Seferos, Dwight S.,Lessard, Beno?t H.,Bender, Timothy P.
, p. 12168 - 12182 (2017)
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.
Water-soluble mitochondrial targeting ethoxy-bromopropyl imidazole axial substituted silicon phthalocyanine and preparation method and application thereof
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Paragraph 0016, (2021/10/05)
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. .
Prop-2-ynyloxybenzyloxy substituted phthalocyanine-based polymeric nanoparticles: synthesis, photophysical properties and in?vitro PDT efficacy
Xiao, Shuanghuang,Chen, Xiuqin,Ye, Qiuhao,Chen, Kuizhi,Xiao, Wenling,Guan, Xinqiao,Huang, Bingcheng,Liu, Guowei,Wei, Hui,Peng, Yiru
, p. 1232 - 1244 (2020/06/17)
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.
Triphenylamine-based branch ligand substituted silicon phthalocyanine, preparation method and application thereof
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Paragraph 0017, (2019/01/08)
The invention discloses a triphenylamine-based branch ligand substituted silicon phthalocyanine, a preparation method and an application thereof. 4-bromotriphenylamine and 4-hydroxy phenylboronic acidare catalytically coupled through tetrakis (triphenylphosphine) palladium, so as to acquire a branch precursor 4'-(diphenyl amino)-[1,1'-biphenyl]-4-alcohol; the 4'-(diphenyl amino)-[1,1'-biphenyl]-4-alcohol (TPA-OH) reacts with SiPcCl2 in the presence of methylbenzene and K2CO3, so as to acquire bi-(4-(diphenyl amino)-1-biphenylyloxy) axially substituted silicon phthalocyanine; steric hindranceof a triphenylamine substituted branch structure is capable of restraining the gathering of phthalocyanine to some extent; the triphenylamine with an aggregation-induced emission characteristic is introduced into the branch structure, so that the 'aggregation-induced quenching' effect of phthalocyanine is improved, the optical physical property of phthalocyanine is regulated and the simultaneous execution of fluorescence imaging and photodynamic therapy is realized; the triphenylamine-based branch ligand substituted silicon phthalocyanine can be used as a fluorescence imaging agent and a photodynamic therapy photosensitizer.
