Zinc phthalocyanine derivative

The pseudorotaxane self-assembles through hydrogen bonding, and the binding constant, calculated using steady-state fluorescence, is 1.4 x 10. The zinc phthalocyanine derivative exhibited an excited-state lifetime of approximately 3.1 ns. The fast decay of the excited state of 1 ZnPc upon complexation with the fullerene... 

S.V. Kudrevich, N. Brasseur, C. La Madeleine, S. Gilbert, J.E. van Lier (1997). Syntheses and photodynamic activities of novel trisulfonated zinc phthalocyanine derivatives. J. Med. Chem., 40, 3897-3904. 

Several zinc(II) and aluminum(III) phthalocyanine derivatives substituted with carboxylic acid and sulfonic acid groups were anchored to nanocrystalline Ti02 films and tested for their photovoltaic behavior.72,73 Interestingly, zinc(II)-2,9,16,23-tetracarboxyphthalocyanine (55) exhibited 45% monochromatic current conversion efficiency at 700 nm. It is shown that electron injection to Ti02 occurs from the excited singlet state of the phthalocyanine derivatives. The... 

In activated sludge, 80.6% degraded after a 47-h time period (Pal et al., 1980). Chemical/Physical. Zhang and Rusling (1993) evaluated the bicontinuous microemulsion of surfactant/oil/water as a medium for the dechlorination of polychlorinated biphenyls by electrochemical catalytic reduction. The microemulsion (20 mL) contained didodecyldi-methylammonium bromide, dodecane, and water at 21, 57, and 22 wt %, respectively. The catalyst used was zinc phthalocyanine (2.5 nM). When PCB-1221 (72 mg), the emulsion and catalyst were subjected to a current of mA/cm on 11.2 cm lead electrode for 10 h, a dechlorination yield of 99% was achieved. Reaction products included a monochlorobiphenyl (0.9 mg), biphenyl, and reduced alkylbenzene derivatives. 

Porphyrin and its derivatives are well-known model compounds for photosynthetic processes that involve charge separation [87], A zinc porphyrin, a copper porphyrin, and a zinc phthalocyanine (Pc) are chosen and incorporated into PPV backbones. Four polymers are synthesized via the Heck polycondensation [88], The incorporation of these metal complex moieties in polymers XI to XIII is manifested by the appearance of Q bands from metalloporphyrin and zinc Pc... 

Zhang and Rusling [66] employed a stable, conductive, bicontinuous microemulsion of surfactant/oil/water as a medium for catalytic dechlorination of PCBs at about 1 mA cm-2 on Pb cathodes. The major products were biphenyl and its reduced alkylbenzene derivatives, which are much less toxic than PCBs. Zinc phthalocyanine provided better catalysis than nickel phthalocyanine tetrasulfonate. The current efficiency was about 20% for 4,4 -DCB and about 40% for the most heavily chlorinated PCB mixture. A nearly complete dechlorination of 100 mg of Aroclor 1260 with 60% Cl was achieved in 18 hr. Electrochemical dehalogenation was thus shown to be feasible in water-based surfactant media, providing a lower-cost, safer alternative to toxic organic solvents. 

A recent exciting development [132, 133] of this chemistry involves conversion of perfluoro(4,5-di-isopropyl)phthalonitrile to corresponding metal perfluorophthalocyanine complexes for example, when perfluoro(4,5-di-isopropyl)phthalonitrile was melted with zinc acetate at 180°C, a blue-green solid was obtained which was established as the phthalocyanine derivative. These perfluoroalkyl derivatives are much more soluble than other halogenated phthalocyanines and, moreover, they appear to be excellent sensitisers for the production of singlet oxygen. 

The preparation of a novel pentadentate ligand, 2-hydroxy-5-methylisophthalalde-hyde bis(p-methoxy thiobenzoylhydra-zone), was described together with the chloro-bridged Zn(II) complexes [127]. Synthesis and electrochemical properties of some long-chain 1,4,8,11,15,18,22,25-ocla-alkylaled metal-free and zinc phthalocyanines were presented by Swarts etal. [128]. Ihe zinc derivatives show higher liquid crystalline behavior than the free-metal compounds. 

Iron and copper phthalocyanines catalyze the isomerization of dimethyl maleate to dimethyl fumarate in the vapor phase at 300°C. No catalytic activity was observed in solution (338). Magnesium and zinc phthalocyanines catalyze the polymerization of methyl methacrylate when illuminated (Xm 600 m/i) (197). Manganous phthalocyanine (88) and ferrous phthalocyanine (59) catalyze the aerial oxidation of benzyl alcohol to benzaldehyde. The catalytic oxidation of ascorbic acid, using magnesium and copper derivatives, is light-sensitive (190, 310). a-Tetralin is catalytically oxidized, in the presence of the magnesium, zinc, or iron complexes, to a-tetralone, the reaction being chemiluminescent (60, 61,158,169, 371). The oxidation of luminol to 5-aminophthalazine-l,4-dione, catalyzed by iron phthalocyanine, is also chemiluminescent (61, 345, 361). 

Because of space limitations, we will only briefly discuss the most basic application in the area of porphyrin optical spectra. Much work has already been done in this area, both with TDDFT and related methods. The TDDFT applications include free base porphin and its ss-octahalogenated derivatives, the porphyrinato-porphyrazinato-zirconiumhV) complex, NiP, NiPz, NiTBP, and NiPc, zinc phthalocyanine, chlorophyll a, zinc complexes of porphyrin, tetraazaporphyrin, tetrabenzoporphyrin, phthalocyanine, phenylene-linked free-base and zinc porphyrin dimers, metal bis(porphyrin) complexes a series of porphyrin-type molecules, and many more. We refer to ref. 75 for an extensive discussion of TDDFT calculations on the spectra of porphyrins and porphyrazines, as well as their interpretation. For further theoretical work on porphyrines, we mention ref. 76 and other papers in that special issue. 

For single-laser-based combined phototherapy, Yudasaka did pioneering work which combines a zinc phthalocyanine (ZnPc) photosensitizer with bovine serum albumin (BSA)-coated CNT derivatives, carbon nanohorns. In this work, carbon nanohorns served as both photosensitizer carrier and photothermal agent. A single 670 nm laser was used to simultaneously activate ZnPc photosensitizer and carbon nanohorn for synergistic phototherapy. This combined phototherapy exhibited a superior anticancer effect both in vitro and in vivo compared with PDT or PTT alone. 

Rio, Y. et al. A panchromatic supramoleeular fullerene-based donor—acceptor assembly derived from a peripherally substituted bodipy-zinc phthalocyanine dyad. Chem. Eur. J. 16, 1929-1940, 2010. 

Phthalocyanine compounds could be extremely promising materials for this application s ll Sulfonic acid derivatives of chloroaluminum phthalocyanine and zinc phthalocyanine have been investigated in detail. Sulfonic acid substituents appear to exhibit optimum value. For zinc phthalocyanine, the disulfonic acid is the most effective. In most cases, these materials are reported to be highly selective in tissue accumulation and more sensitive than porphyrin compounds. 

Porphyrins and phthalocyanines also act as donors for fuiierenes under photoexcitation [54, 55]. It was confirmed that the electron transfer proceeded via both and triplet excited porphyrins. Zinc-including porphyrin compounds such as tetraphenylporphyrin and octaethyl-porphyrin showed higher donor ability to fuiierenes in comparison with copper and H incorporated porphyrins. A similar tendency was also confirmed with phthalocyanine derivatives [55]. 

Zhao Z-H, Fan J-M, Wang Z-Z (2007) Photo-catalytic CO2 reduction using sol-gel derived titania-supported zinc-phthalocyanine. J Clean Prod 15 1894—1897... 

The number and position of the sulfonic acid substituents in zinc(II) phthalocyanine have an appreciable effect on bioactivity. Partial sulfonation gives the greatest activity, and the S2a derivatives (two sulfonic acid substituents on adjacent benzene rings) appear to be the most active.254,255 While this can be readily understood in general terms of developing amphiphilic character (Section 9.22.3), the detailed mechanism responsible for this result is not yet clear. The aggregation of zinc(II) sulphonic acid derivatives in solution and in tissue has been studied in relation to PDT.256... 

A series of zinc(II) phthalocyanines with other sorts of solubilizing groups in exo or endo positions (carboxyalkyl, carboxyalkoxy, amino acid) has been synthesized and subjected to preliminary in vitro assays.257 Interestingly, the seryl derivative zinc(II) 2,9,16,23-tetrakis(l-car-boxy-2-hydroxyethylaminocarbonyl)phthalocyanine proved to be cytotoxic (i.e., toxic in the dark) which is not so commonly observed with macrocyclic systems. 

Several studies have been reported on the biological mechanisms of zinc(II) phthalocyanines as photosensitizers. In vitro studies (mouse RIF-1 cells) on zinc(II) phthalocyanines differing in overall charge (tetrapyridinium quaternary salt tetrasulfonic acid tetrasulfonamide derivative ... 

---