Quaternized phthalocyanines and method for photodisinfection of water

FIELD: chemistry, chemical technology.

SUBSTANCE: invention relates to quaternized phthalocyanines and their using for treatment of water against bacterial pollution. Invention describes novel quaternized phthalocyanines representing poly-(trialkylammoniomethyl)-substituted zinc and aluminum phthalocyanines that are sensitizing agents in formation of singlet oxygen by effect of visible light. Also, invention relates to a method for photodisinfection of water by using these quaternized phthalocyanines or their mixtures with dyes of acridine, rhodamine or phenothiazine series and radiation in visible range in the presence of oxygen that provides the effective treatment of water against bacterial pollution.

EFFECT: valuable properties of compounds, improved method of water treatment.

3 cl, 5 tbl, 16 ex

 

The present invention relates to chemistry and chemical technology, more precisely, to the cationic phthalocyanines, namely quaternions the phthalocyanines and their use for water purification from bacterial contamination.

Sensitized oxidation of singlet oxygen is used in various fields, including for water purification from impurities [..Derosa, R.J.Crutchley. Coord. Chem. Rev. 2002. V.233-234. R-371], bleach [US Patent PCT Iit. Appl. WO 9832828, CL. 11 D 3/00, CA 1998: 129: 163143v], inactivation of microorganisms [G.Jori, S.Brown. Photochem. Photobiol. Sci. 2004. V3. P.403-405].

Known octakis(pyridiniomethyl)substituted zinc phthalocyanines (ZnPcPym8) and aluminum (AlPcPym8). The positive charge ensures the interaction of these sensitizers with negatively charged outer membrane of microorganisms, contamination and effective photodynamic inactivation. Also known compositions, which include ZnPcPym8, AlPcPym8and acridine dyes, radominova or phenothiazine series [RF patent №2235688, CL 02 F 1/32, 2002] for Photobacterium water. According to the patent of Russian Federation №2235688, CL 02 F 1/32, 2002 Photobacterium water use sensitizers of active forms of oxygen and emission of visible range. Used in the composition of photoactive dyes absorb in other spectral regions of the visible range. Thus the use is of omposite allows to increase the efficiency of utilization of light energy and increase Photobacterium effects of drugs.

However, given the diversity of pathogenic microorganisms with different affinity for different organic molecules needed a wide range of photosensitizers for more complete and effective disinfection of water objects.

The objective of the invention is to find new cationic phthalocyanine derivatives effectively sensitizing the formation of singlet oxygen under the action of visible light and inactivating microorganisms, as well as the development method Photobacterium water with their application.

The problem is solved by the synthesis of new cationic phthalocyanines - quaternionic phthalocyanines of General formula:

where:

M=Zn, AlY,

n=6÷8,

R1÷R3=alkyl or substituted alkyl,

X-=anion,

Y=Cl, OH, OSO3H.

Offer phthalocyanine sensitizers are easily dissolved in water. They absorb visible light range with a wavelength in the region from 600 to 700 nm.

The task is also achieved by providing a method of Photobacterium water using the above quaternionic phthalocyanines. For its solution is proposed a method of Photobacterium water using sensitizer cationic type and radiation of the visible range in the presence of the of ikorodu, characterized in that the sensitizer is used above quaternionic phthalocyanine or a mixture of acridine dyes, radominova or phenothiazine series.

The invention is illustrated by the following examples.

Example 1

To 2.5 g (2.58 mmol) chlorocinnamate phthalocyanine zinc with an average number chloromethylene groups of 8 (found, %: Cl 29.05; calculated, %: Cl 29.36)obtained by analogy with the English patent 844338 (1953), add 5 ml of dimethylformamide and 5 ml of N,N-dimethylaminoethanol. The mixture is stirred for 2 h at 100°C, the precipitation is filtered off, washed with acetone and dried, yielding 3.4 g (78.3%) octakis(N-(2-hydroxyethyl)-N,N-dimethylaminomethyl)phthalocyanine zinc octaploid (ZnPcChoI8). The electronic absorption spectrum, λmaxnm (H2O): 679-680. Found, %: C at 51.47; H 6.84; N, 13.07; Cl 15.88. Calculated for C72H112Cl8N16O8Zn, %: 51.50; N, 6.72; N, 13.35; Cl 16.89.

Example 2

Analogously to example 1 from chlorocinnamate phthalocyanine chloramine with the average number chloromethylene groups of 8 (found, %: Cl 32.50; calculated for (ClCH2)8-PcAlCl, %: Cl 33.14)obtained by analogy with the English patent 844338 (1953), receive N-(2-hydroxyethyl)-N,N-dimethylaminomethylene phthalocyanine chloramine with an average degree of substitution, RA is Noah eight (AlPcChol 8). The electronic absorption spectrum, λmaxnm (H2O): 682-684.

Example 3

Analogously to example 1 from chlorocinnamate phthalocyanine zinc with an average number chloromethylene groups, equal to 6 (found, %: Cl 24.98; calculated for (ClCH2)6-PcZn, %: Cl at 24.48), get hexacis(N(2-hydroxyethyl)-N,N-dimethylaminomethyl)phthalocyanine zinc hexachloride (ZnPcChol6). The electronic absorption spectrum, λmaxnm (H2O): 677-679.

Example 4

To 0.50 g (0.51 mmol) octakis(chloromethyl)phthalocyanine zinc with an average number chloromethylene groups, equal to 8, add 2 ml of dimethylformamide and 3 ml of N,N,N',N'-tetramethylethylenediamine. After the dissolution of the original phthalocyanine mixture is stirred for 1 h at 100°deposited precipitate was separated, washed with dimethylformamide, acetone and dried, yielding 0.71 g (73%) octakis(N-(2-(dimethylamino)ethyl)-N,N-dimethylaminomethyl)phthalocyanine zinc octaploid (ZnPcTmed8). The electronic absorption spectrum, λmaxnm (N2): 679. Found, %: 55.45; N, 7.68; N 17.09; Cl 15.05. Calculated for C88H152Cl8N24Zn, %: 55.70; N, 8.08; N 17.70; Cl 14.92.

Example 5

A mixture of 0.1 g of the complex obtained in example 4, and 5 ml of methanol and 3 ml under the conditions stirred at 40°C for 3 hours the Precipitate was separated, washed with methanol and dried, yielding 0.12 g (75%) octakis(N,N-dimethyl-N-(2-(trimethylammonio)ethyl)Ammon shall said;") phthalocyanine zinc attitide of octaploid (ZnPcPmed 8). The electronic absorption spectrum, λmaxnm (H2O): 680. Found, %: C is the 38.20; N, 5.65; N, 10.75; Cl 9.05. Calculated for C96H176Cl8I8N24Zn, %: C 38.04; N, 5.85; N, 11.08; Cl 9.35.

Example 6

Analogously to example 1 from chlorocinnamate aluminum phthalocyanine with an average degree of substitution equal to six (found, %: Cl 23.27; calculated for (ClCH2)6-PcAlOSO3H, %: Cl 22.93), get hexacis(N-(2-hydroxyethyl)-N,N-dimethylaminomethyl)phthalocyanine the hydrosulfate aluminum hexachloride (AlPcChol6). The electronic absorption spectrum, λmaxnm (H2O): 680-682.

Example 7

To 0.5 g (0.51 mmol) chlorocinnamate phthalocyanine zinc with an average number chloromethylene groups, equal to 8, add 3 ml of dimethylformamide and 3 ml of triethanolamine. The mixture is stirred for 1 h at 100°C, the precipitation is filtered off, washed with acetone, periostat from methanol-ether and dried, yielding 0.57 g (51.0%) octakis(N,N,N-Tris(2-hydroxyethyl) ammoniated)phthalocyanine zinc octaploid (ZnPcThea8).

Example 8

The determination of the relative activity of photosensitizers in the generation of active singlet oxygen in the water

To test the effectiveness of photogeneration of singlet oxygen in the water used water-soluble cationic trap singlet oxygen - bis-9,10-(4-trimethylammoniumphenyl)antrac the n dichloride (VRA) [V.Nardello, J.-M.Aubry. Tetrahedron Lett. 1997. V.38. N42. R-7364]. The solution under test phthalocyanine with a concentration of about 5×10-6mol/l, containing 5×10-5mol/l VRAA, were placed in a standard spectrophotometric cuvette with an optical layer thickness of 1 cm and irradiated with the light bulb DXS-150 through a glass filter LGL-18 and an interference filter with a maximum bandwidth of 680 nm. The intensity of the light flux was determined using a power meter Spectra Physics-404, the proportion absorbed by the sample light was calculated by integrating the overlapping absorption spectra of the filter and the absorption spectrum of the dyes. Photocatalytic oxidation of the acceptor singlet oxygen was monitored spectrophotometrically by the decrease in the absorption maximum at the wavelength of 393 nm. The quantum yield for the generation of singlet oxygen was calculated relative to ZnPcPym8under the condition of constancy of the concentration of traps, using the relationship:

where ϕΔand ϕΔChol- quantum yields of generating singlet oxygen,

w and wChol- speed spending VRAA,

I, IChol- number of light quanta absorbed by sensitizers per unit time.

The value of the relative quantum outputs sensitization education singlet color is Yes visiophone quaternidinum the phthalocyanines are shown in table 1.

Table 1
The relative quantum yields of photogeneration singlet oxygen quaternidinum the phthalocyanines in the water
№ p/pThe sensitizerλmaxnmϕRel
1ZnPcPym8(similar)6801.00
2ZnPcPmed86791.45
3ZnPcChol86801.30
4ZnPcTmed86771.20
5AlPcPym8(similar)6800.75
6AlPcChol86840.55
7AlPcChol66830.50

From table 1 it follows that proposed in the present invention quaternion phthalocyanines effectively sensibiliser the formation of the active singlet oxygen in the aquatic environment and on the activity of photogeneration singlet oxygen in some cases surpass analogues.

Example 9

Definition of quantum outputs the generation of singlet oxygen in alcohol environments

Values ϕΔ/sub> for the proposed in the present invention quaternionic phthalocyanines in alcohols was determined as described in example 1 using 1,3-diphenylisobenzofuran as chemical acceptor singlet oxygen and standard methylene blue. Determined the absolute value of the ϕΔ(table 2), because the values ϕΔfor methylene blue in ethanol environments known (0.5 in methanol and 0.52 in ethanol [..Derosa, R.J.Cmtchley. Coord. Chem. Rev. 2002. V.233-234. R-371]).

Table 2
Quantum yields of photogeneration singlet oxygen quaternidinum the phthalocyanines in alcoholic media
№ p/pThe sensitizerSolventλmaxnmϕΔ
1ZnPcPym8(similar)Methanol6830.20
2ZnPcChol8Ethanol6770.62
3Methanol6800.55
4ZnPcThea8Methanol6790.25
5Ethanol680 0.25
6AlPcChol8Methanol6840.27

From the data of table 2 it follows that proposed in the present invention quaternion phthalocyanines effectively sensibiliser the formation of the active singlet oxygen and non-aqueous, in particular alcohol, environments and activity superior to analogue.

Example 10

The determination of the activity of photosensitizers during the photo-oxidation of model organic substrate

As a model organic substrate used organic acid tryptophan, which is part of biomolecules. Take 3.5×10-4mol/l tryptophan and 3.5×10-4mol/l quaternionic phthalocyanine in water, placed in a quartz cuvette with an optical layer thickness of 1 cm and irradiated with continuous bubbling of air. The light source lamp of SIRS-6-100. To highlight the light of the spectral range corresponding to long-wavelength absorption band of the sensitizers used filter KS-10. Spending tryptophan was monitored spectrophotometrically by the decrease in optical density at the maximum at a wavelength of 218 nm. The speed of the sensitized oxidation of tryptophan was estimated by the initial linear section of the kinetic curve. The relative rate of oxidation of tryptophan, Sensi is alizirovannoj proposed in the present invention sensitizers (W Rel)given in table 3.

Table 3
The relative efficiency quaternionic phthalocyanines in the process sensitised oxidation of tryptophan
№ p/pThe sensitizerWRel
1ZnPcPym8(similar)1.00
2ZnPcPmed8of 1.34
3ZnPcChol81,22
4ZnPcTmed80,88
5AlPcPym8(similar)0,84
6AlPcChol80,92
7AlPcPmed80,70

As can be seen from the results shown in table 3, all tested quaternion phthalocyanines on the effectiveness of sensitization of the oxidation of tryptophan comparable with analogues ZnPcPym8, AlPcPym8and in cases ZnPcChol8and ZnPcPmed8surpass it.

Example 11

Prepared solution quaternionic phthalocyanine (sensitizer) in bacterial contaminated water. Before irradiation the solution was incubated for 1 hour, then placed in the reactor (V=200 ml)equipped with a jacket for chilled is I the current of water, and were irradiated 30 min visible light from an external source. The light source was a halogen bulb R7s by OSRAM power 300 W, located in the spotlight at a distance of 15 cm from the reactor. The solution during irradiation were mixed and aeronavali by bubbling air. For determination of coliform bacteria (total coliforms, OKB) microorganisms from 100 ml of water was sown on the membrane filters were then incubated in a thermostat at 37°With during the day. Counted the number of colonies (CFU). The effectiveness of Photobacterium was determined by the formula:

The results are presented in table 4.

Table 4
№ p/pThe sensitizerConcentration, mg/lOKB (CFU per 100 ml)Efficiency, %
Before processingAfter processing
9ZnPcPym8(similar)2720898.90
1ZnPcChol8333000100.00
227200100.00
3 33004098.80
40.533008097.60
5ZnPcPmed8415000100,00
62.51500199.93
7AlPcChol82720499.45
81hl627201098.60

Proposed in the present invention quaternion phthalocyanines are active photodisintegrate coliforms in water (table 4) and in some cases exceed-action counterpart.

Examples 12-16

In the solution of bacterial contaminated water was injected composition of sensitizers, were incubated for 1 hour, then was irradiated for 30 minutes and analyzed for the content of OKB similar to that described in example 11. The compositions, the concentration of the components and the results obtained by Photobacterium action against the Bureau are summarized in table 5.

ZnPcPym8(0.8 mg/l)
Table 5
Data Photobacterium water compositions photosin is ivilization
№ p/pTrackOKBEfficiency, %
before processingafter processing
12ZnPcChol8(1 mg/l)13000100
Proflavin (0.5 mg/l)
ZnPcPmed8(1.5 mg/l)
13Dibromomethyl rhodamine 123 (0.3 mg/l)13000100
Methylene blue (0.2 mg/l)
14AlPcChol8(0.5 mg/l)1050100
Proflavin (0.3 mg/l)
ZnPcPym8(0.8 mg/l)
15Acridine yellow (0.2 mg/l)1500399.8
(Pat. RF 2235688)
16Acridine yellow (0.4 mg/l)15000100
(Pat. RF 2235688)

The data of table 5 demonstrate higher efficacy of the proposed phtalocyanine dyes together with proflavine, methylene blue and dibromsalan by rhodamine 123.

Thus,

new, proposed in this invention quaternion phthalocyanines are efficient sensitizers of singlet oxygen in aqueous and nonaqueous media and by the activity of photogeneration singlet oxygen in some cases surpass analogue;

b) application of the proposed connections to Photobacterium water, as such or in a composition with dyes radominova, acridine and phenothiazine series, provides an effective Photobacterium water, and proposed phthalocyanines in some cases are more effective than known similar.

1. Quaternion phthalocyanines of General formula

where

M=Zn, AlY,

n=6÷8,

R1÷R 3=alkyl or substituted alkyl,

X'=anion,

Y=Cl, HE, OSO3N.

2. How Photobacterium water using sensitizer cationic type and radiation of the visible range in the presence of oxygen, characterized in that the sensitizer is used as a compound according to claim 1 or a mixture of acridine dyes, radominova or phenothiazine series.



 

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