Cross-conjugated ω,ω′-bis(dimethylamino) ketones and dinitriles containing a cycloalkane or piperidine fragment: Synthesis and study of spectroscopic properties

Article abstract of DOI:10.1007/s11172-010-0009-3

N-Substituted 4-piperidones react with β-dimethylaminoacrolein aminals to give keto-cyanines containing a piperidine ring. A reaction of 3-dimethylamino-1, 1,3-trimethoxypropane with 1-ethoxycarbonylpiperidin-4- ylidenemalononitrile produces a cross-conju

Full text of DOI:10.1007/s11172-010-0009-3

Russian Chemical Bulletin, International Edition, Vol. 58, No. 2, pp. 317—321, February, 2009
317
Crossꢀconjugated ω,ω´ꢀbis(dimethylamino) ketones and dinitriles
containing a cycloalkane or piperidine fragment:
synthesis and study of spectroscopic properties*
Zh. A. Krasnaya,a L. A. Shvedova,b A. S. Tatikolov,b E. O. Tret´yakova,a V. V. Kachala,a and S. G. Zlotina
aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky prosp., 119991 Moscow, Russian Federation.
Fax: +7 (499) 135 5328. Eꢀmail: kra@ioc.ac.ru
bN. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences,
4 ul. Kosygina, 119991 Moscow, Russian Federation.
Fax: +7 (499) 137 4101. Eꢀmail: shvedova@sky.chph.ras.ru
NꢀSubstituted 4ꢀpiperidones react with βꢀdimethylaminoacrolein aminals to give ketoꢀ
cyanines containing a piperidine ring. A reaction of 3ꢀdimethylaminoꢀ1,1,3ꢀtrimethoxypropane
with 1ꢀethoxycarbonylpiperidinꢀ4ꢀylidenemalononitrile produces a crossꢀconjugated ω,ω´ꢀbisꢀ
(dimethylamino) dinitrile. Its yield is doubled when ionic liquids are used. The spectroscopic
properties of the compounds obtained are highly sensitive to the structure: replacement of the
C=O group in ketocyanines by the C=C(CN)2 group results in a considerable bathochromic
shift of the absorption spectra, while replacement of the central bridging fragment (CH2)3 by
(CH2)4 results in a hypsochromic shift. All the compounds obtained exhibit positive
solvatochromism.
Key words: malononitriles, ketocyanines, βꢀdimethylaminoacrolein aminal, 3ꢀdimethylꢀ
aminoꢀ1,1,3ꢀtrimethoxypropane, ionic liquids, electronic absorption spectra, chromoꢀ
phores, dyes.
Earlier, we have developed methods for the synthesis
of ketocyanines, ω,ω´ꢀbis(dimethylamino polyenyl) keꢀ
tones (BDAK), which are bichromophoric crossꢀconjuꢀ
gated systems with two polyene chains coupled through a
carbonyl group.1—3 The terminal substituents are elecꢀ
tronꢀdonating dimethylamino groups and the central subꢀ
stituent is an electronꢀwithdrawing carbonyl group.
photochemical processes (e.g., interactions of the chroꢀ
mophores in the singletꢀ and tripletꢀexcited states1,8,9).
Recently,10 we have obtained new analogs of BDAK,
viz., crossꢀconjugated α,α´ꢀbis(3ꢀdimethylaminopropꢀ
2ꢀenylidene)cycloalkylidenemalononitriles 1a—c conꢀ
taining the dicyanomethylidene fragment instead of the
carbonyl group.
BDAK (n = 1, 2; m = 1—3)
n = 1 (a), 2 (b), 3 (c)
Owing to their electronic structure, BDAK exhibit
pronounced solvatochromism,4,5 strong thermochromism,6
intense fluorescence, and generation of laser radiation.7
Being structurally simple, these compounds are conveꢀ
nient models for the study of various photophysical and
According to recent data,11,12 cyanoꢀcontaining polyꢀ
enes can be employed as materials for nonlinear optics. In
addition, interesting fluorescent features have been disꢀ
covered in merocyanine dyes with electronꢀwithdrawing
dicyano substituents.13,14 Therefore, one can assume that
combination of a dimethylamino polyene chain and a
cyano group in compounds 1a—c will impart valuable
properties to these compounds.
* On the occasion of the 75th anniversary of the foundation
of the N. D. Zelinsky Institute of Organic Chemistry of the
Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 315—319, February, 2009.
1066ꢀ5285/09/5802ꢀ0317 © 2009 Springer Science+Business Media, Inc.

318
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 2, February, 2009
Krasnaya et al.
Scheme 2
The goal of the present work was to obtain new
ketocyanines containing the 4ꢀpiperidone ring and their
dicyanomethylidene analogs and compare their spectroꢀ
scopic properties.
Condensation of βꢀdimethylaminoacrolein aminal 2
(see Ref. 15) with Nꢀsubstituted 4ꢀpiperidones 3a,b
(75—80 °C, 60—90 min) gave ketocyanines 4a,b in 90%
yields (Scheme 1).
Scheme 1
R = Me (a), CO2Et (b)
To obtain conjugated dinitriles 5a,b, which are dicyanoꢀ
methylidene analogs of ketocyanines 4a,b, we studied
condensations of aminal 2 and 3ꢀdimethylaminoꢀ
1,1,3ꢀtrimethoxypropane (6)16 with 1ꢀmethylpiperidinꢀ
4ꢀylidenemalononitrile (7a)17 and 1ꢀethoxycarbonylꢀ
piperidinꢀ4ꢀylidenemalononitrile (7b) (Scheme 2).
Attempted synthesis of polyene dinitriles 5a,b via
condensation of dinitriles 7a,b with aminal 2 was unsucꢀ
cessful.
R = Me (a), CO2Et (b)
solvents with different polarities for ketocyanines 4a,b,
dinitrile 5b, crossꢀconjugated dinitriles 1a—c (see Ref. 10),
and ketocyanines 8a—c (see Refs 2, 3).
However, a condensation of reagent 6 with dinitrile 7b
(unlike dinitrile 7a) gave crossꢀconjugated dinitrile 5b.
The yield of product 5b depends on the reaction condiꢀ
tions: 23% for neat reagents and 43% in the presence of
ionic liquids (1ꢀbutylꢀ3ꢀmethylimidazolium tetrafluoroꢀ
borate [bmim]BF4 or 1ꢀbutylꢀ1ꢀmethylpyrrolidinium
bis(trifluoromethylsulfonyl)imide). The structures of
crossꢀconjugated polyenes 4a,b and 5b obtained as bright
red (4a,b) and brown crystals (5b) were determined from
1H and 13C NMR, UVꢀVis, and mass spectra and elemenꢀ
n = 1 (a), 2 (b), 3 (c)
The absorption peaks in the spectra of the above
ketocyanines and dinitriles are given in Table 1. It should
be noted that the emission intensities of the dinitriles are
substantially lower than those of ketocyanines (see data
from emission measurements18). Since the absorption
band of the dinitriles and the ketocyanines shift to the
longer wavelengths when polar solvents are used instead
of nonpolar ones (positive solvatochromism), this band is
obviously due to an intramolecular charge transfer. The
amino groups in both the ketocyanines and dinitriles are
electron donors, while the cyano fragments in the dinitriles
are electron acceptors (like the carbonyl group in the
1
tal analysis data. For signal assignments in the H and
13C NMR spectra, 2D COSY, HSQC, and HMBC
experiments were carried out. The vicinal constants
3
3Jβ γ and Jγ−δ (12.0 and 12.4 Hz, respectively) suggest a
ꢀ
Eꢀconfiguration of the double bonds and an Sꢀtransꢀconꢀ
formation of the diene fragment in these compounds.
The influence of the structure of crossꢀconjugated
ω,ω´ꢀbisamino polyenes and the solvating effect of the
solvent on their spectroscopic properties were studied in

Crossꢀconjugated diamino ketones and nitriles
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 2, February, 2009
319
Table 1. Absorption peaks of the dyes in solvents with different
polarities
Table 2. Absorption peaks of mono(dimethylamino) ketones and
dinitriles in ethanol and the shifts Δν and Δλ of the peaks for the
corresponding ketone—dinitrile pairs
Compound
λ
max/nm
EtOH
Mono(dimethylamino)
ketones
Mono(dimethylamino)
dinitriles
Δν/cm–1
(Δλ/nm)
Heptane
CHCl3
H2O
1a
1b
1c
4a
4b
5b
8a
8b
8c
511
534
438
415
418
—
429
416
372
568
546
494
460
460
540
475
460
419
583
575
512
490
480
575
502
490
446
604
592
539
518
519
—
529
521
477
Comꢀ
pound
ν
max/cm–1
Comꢀ
pound
ν
max/cm–1
(λmax/nm)
(λmax/nm)
9a 2
9b 15
10 2
26310 (380)
22830 (438)
25000 (400)
11a 15 20750 (482) 5560 (102)
11b 15 17240 (580) 5590 (142)
12 10
19230 (520) 5770 (120)
because of its more complex spatial (not planar) conforꢀ
mation characterized by a larger deviation of the central
ketocyanine). The absorption bands of the dinitriles are
strongly (by 70—100 nm) shifted to the longer wavelengths
compared to the corresponding ketocyanines (see Table 1).
This can be associated with the lengthening of the chroꢀ
mophore in the dinitriles by the fragment C=C(CN)2,
which is crossꢀconjugated with the side polyene chains
(the chromophores are chains from the amino group (an
electron donor) to the C≡N groups (electron acceptors)).
It should be noted that when both polyene chromophores
in ketocyanines are lengthened by one unit, the absorption
band of the dye is shifted by ~95 nm,8 while a lengthening
of only one chromophore results in a shift only by ~25 nm
(see Refs 4, 8).
part (Cα—C(1)—Cα ) from the conjugation plane.
´
The solvatochromic shifts for the ketocyanines are
much larger than those for the dinitriles (Table 3). This is
because ketocyanines contain the carbonyl group tending
to form hydrogen bonds in electrophilic solvation. Ketoꢀ
cyanines can be easily protonated and alkylated to give
polymethine salts with equalized C—C bonds, which is
confirmed by their 13C NMR spectra (see Refs 6, 19, 20).
Unlike ketocyanines, dinitriles contain no carbonyl group;
so they are not protonated and exhibit weaker solvatoꢀ
chromism.
The 13C NMR spectra of dyes 8b and 1b in CDCl3 are
given in Table 4. The chemical shifts and their differences
between adjacent polymethine C atoms suggest a stronger
charge alternation for the Cβ, Cγ, and Cδ atoms in dinitrile
1b compared to ketocyanine 8b. Therefore, the polyꢀ
methine chain of the dinitrile has more equalized bonds
than the chain of ketocyanine 8b (see Refs 19, 20).
In conjugated mono(dimethylamino) ketones, replaceꢀ
ment of the carbonyl group by a dicyanomethylidene fragꢀ
ment brings about a considerable bathochromic shift λmax
(by 100—120 nm), which is evident from the absorption
peaks of compounds 9—12 (Table 2).
Table 3. Shifts of the peaks in the S—S spectra of ketocyanines
8a—c and dinitriles 1a—c in polar and nonpolar solvents
Comꢀ
pound
Solvent
λ
max/nm (ν/cm–1
)
Δν/cm—1
Ketocyanines
8a
8b
Toluene
EtOH
Toluene
452 (22124)
502 (19920)
441 (22675)
2204
—
2267
PriOH
Heptane
MeOH
490 (20408)
372 (26882)
452 (22124)
—
4758
—
8c
n = 2 (a), 3 (b)
Dinitriles
In addition, it can be seen in Table 1 that the dyes
differing only in the size of the central ring absorb at very
different wavelengths: the spectra of ketocyanines and
dinitriles with a sevenꢀmembered central ring experience
a hypsochromic shift compared to their sixꢀmembered
analogs. Apparently, this is due to the weaker conjugation
in the molecules containing the cycloheptane bridge
1a
1b
1c
Toluene
EtOH
Toluene
PriOH
Heptane
MeOH
550 (18182)
583 (17153)
543 (18416)
567 (17637)
372 (26882)
452 (22124)
1029
—
779
—
—
—

320
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 2, February, 2009
Krasnaya et al.
Table 4. 13C NMR spectra and the chemical shift
differences Δδ of the adjacent polymethine C atoms
for dyes 8b and 1b in CDCl3
δꢀH, J = 12.5 Hz); 7.40 (d, 2 H, βꢀH, J = 12.5 Hz). 13C NMR
(DMSOꢀd6), δ: 39.50 (NMe2), 45.93 (NMe); 55.71 (CH2); 93.38
(γꢀC); 120.09 (αꢀC); 136.06 (βꢀC), 151.34 (δꢀC), 181.68 (CO).
MS, m/z 275 [M]+.
3,5ꢀBis(3ꢀdimethylaminopropꢀ2ꢀenylidene)ꢀ1ꢀethoxycarꢀ
bonylpiperidinꢀ4ꢀone (4b). Aminal 2 (0.53 g, 3.1 mmol) was
added dropwise to ethyl 4ꢀoxopiperidineꢀ1ꢀcarboxylate 3b
(0.26 g, 1.5 mmol). The reaction mixture was heated at 80—85 °C
for 1.5 h. The resulting diamino ketone 4b was isolated as
described above. The yield of ketone 4b was 0.45 g (90%), red
crystals, m.p. 182—185 °C. Found (%): C, 64.91; H, 8.18;
N, 12.58. C18H27N3O3. Calculated (%): C, 64.86; H, 8.11;
N, 12.61. UV, λmax/nm (ε): 480 (80 505) (EtOH), 460 (84 165)
Atoms
8b
1b
δ
δꢀC
γꢀC
βꢀC
αꢀC
149.94
95.43
137.69
124.61
152.38
96.62
142.84
122.15
Δδ
1
(CHCl3). H NMR (DMSOꢀd6), δ: 1.17 (m, 3 H, CH3CH2O);
(δꢀC)—(γꢀC)
(βꢀC)—(γꢀC)
(βꢀC)—(αꢀC)
54.51
42.26
13.08
55.76
46.22
20.69
2.90 (s, 12 H, NMe2); 4.03 (q, 2 H, CH3CH2O, J = 7 Hz);
4.25 (s, 4 H, CH2); 4.95 (t, 2 H, γꢀH, J = 12.4 Hz); 7.0 (d, 2 H,
1
δꢀH, J = 12.4 Hz); 7.18 (d, 2 H, βꢀH, J = 12.4 Hz). H NMR
(CDCl3), δ: 1.25 (m, 3 H, CH3CH2O); 2.90 (s, 12 H, NMe2);
4.15 (q, 2 H, CH3CH2O, J = 7 Hz); 4.38 (s, 4 H, CH2); 5.05 (t,
2 H, γꢀH, J = 12.4 Hz); 6.72 (d, 2 H, δꢀH, J = 12.4 Hz); 7.40 (d,
2 H, βꢀH, J = 12.4 Hz). 13C NMR (DMSOꢀd6), δ: 14.54
(OCH2CH3); 39.49 (NMe2); 43.51 (CH2); 60.0 (OCH2CH3);
92.87 (γꢀC); 117.90 (αꢀC); 137.34 (βꢀC); 152.34 (δꢀC); 154.55
(COOEt); 181.17 (CO). MS, m/z 333 [M]+.
Apparently, this is due to the presence of two strong
electronꢀwithdrawing C≡N substituents in the dinitrile
structure and, consequently, stronger intramolecular
donor—acceptor interactions in dinitrile 1b.
Experimental
(1ꢀEthoxycarbonylpiperidinꢀ4ꢀylidene)malononitrile (7b).
A mixture of ethyl 4ꢀoxopiperidineꢀ1ꢀcarboxylate 3b (5 g,
0.03 mol), malononitrile (2.97 g, 0.045 mol), ammonium
acetate (0.89 g), and AcOH (2.04 g) was refluxed in benzene
(15 mL) using a Dean—Stark trap for 1.5 h. The reaction mixꢀ
ture was concentrated in vacuo. Ether (50 mL) was added and an
inorganic precipitate was filtered off. The ethereal solution was
washed with a solution of NHCO3 and water (three times),
dried with calcined MgSO4, and concentrated in vacuo. The
yield of dinitrile 7b was 3.2 g (49%), m.p. 79—84 °C. UV (EtOH),
The NMR spectra of compounds 4a,b and 5b were recorded
on a Bruker DRXꢀ500 spectrometer (500.13 (1H) and 125.76
MHz (13C)) in DMSOꢀd6 (4a,b, 5b) and CDCl3 (4a,b) at 30 °C.
Chemical shifts are referenced to the signals for the carbon
atoms (13C) and those for residual protons in CDCl3 (δ 77.0 and
7.27) and DMSOꢀd6 (δ 39.5 and 2.50) (1H). 2D NMR spectra
were recorded as recommended by Bruker standard procedures.
The 1H NMR spectra of compound 7b were recorded on a
Bruker AMꢀ300 instrument (300 MHz) in CDCl3. Mass spectra
(EI) were measured on a Kratos MSꢀ30 instrument (70 eV).
Electronic absorption spectra were recorded on a Specord UVꢀVIS
instrument. The course of the reactions was monitored by UV
spectroscopy.
The electronic absorption spectra of the dyes were recorded
on a Shimadzu UVꢀ101PC spectrophotometer (l = 1 cm).
Emission and excitation spectra were recorded on a Shimadzu
RFꢀ5301PC spectrofluorimeter. Neither emission nor excitaꢀ
tion spectra were corrected for the spectroscopic sensitivity of
the instrument (the optical densities of solutions during the
emission measurements did not exceed 0.1).
3,5ꢀBis(3ꢀdimethylaminopropꢀ2ꢀenylidene)ꢀ1ꢀmethylpiperiꢀ
dinꢀ4ꢀone (4a). Aminal 2 (0.85 g, 4.9 mmol) was added dropwise
to 1ꢀmethylꢀ4ꢀpiperidone 3a (0.226 g, 2 mmol). The mixture
was heated at 75—80 °C for 50 min. The crystallized mixture
was concentrated in vacuo. Anhydrous ether was added to the
residue and the resulting precipitate was separated and washed
with anhydrous ether. The yield of diamino ketone (4a) was 0.5 g
(90%), red crystals, m.p. 186—188 °C. Found (%): C, 69.70; H,
9.13; N, 15.28. C16H25N3O. Calculated (%): C, 69.81; H, 9.09;
λ
max/nm (ε): 228 (9000), 270 (5760). 1H NMR (CDCl3), δ: 1.30
(t, 3 H, CH3CH2O); 2.75 (m, 4 H, CH2); 3.65 (m, 4 H, CH2);
4.30 (q, 2 H, CH3CH2O). MS, m/z 219 [M]+.
[3,5ꢀBis(3ꢀdimethylaminopropꢀ2ꢀenylidene)ꢀ1ꢀethoxycarꢀ
bonylpiperidinꢀ4ꢀylidene]malononitrile (5b). A. 3ꢀDimethylꢀ
aminoꢀ1,1,3ꢀtrimethoxypropane (6) (0.49 g, 2.8 mmol) was
added dropwise to dinitrile 7b (0.2 g, 0.93 mmol). The reaction
mixture was stirred at 75—80 °C for 3 h, kept at 20—25 °C for a
day, and concentrated in vacuo. Water (10 mL) was added and
a precipitate was filtered off and washed with water and ether.
The precipitate was dissolved in CHCl3 (70 mL) and kept over
SiO2 (L 40/100, 0.4 g) for a day. The silica was separated, the
solution was concentrated, and ether was added to the residue.
The precipitate was filtered off and washed with ether. The yield
of dinitrile 5b was 0.08 g (23%), brown crystals, m.p. >260 °C.
Since compound 5b is a highꢀmelting solid, its elemental analyꢀ
sis failed. UV, λmax/nm (ε): 575 (62 120) (EtOH), 540 (61 290)
(CHCl3). 1H NMR (DMSOꢀd6), δ: 1.15 (t, 3 H, CH3CH2O);
3.02 (s, 12 H, NMe2); 4.00 (s, 4 H, CH2); 4.08 (q, 2 H,
CH3CH2O); 5.40 (t, 2 H, γꢀH, J = 12 Hz); 7.35 (d, 4 H, βꢀH
and δꢀH). 13C NMR (DMSOꢀd6), δ: 13.9 (OCH2CH3); 41.9
(CH2); 60.9 (OCH2CH3); 97.2 (γꢀC); 145.6 (βꢀC); 155.7 (δꢀC).
A number of signals were not accumulated because of the poor
solubility of the sample. MS, m/z 381 [M]+.
N, 15.27. UV, λ /nm (ε): 490 (97 600) (EtOH), 470 (72 600)
max
(CHCl3). 1H NMR (DMSOꢀd6), δ: 2.32 (s, 3 H, NMe); 2.85 (s,
12 H, NMe2); 3.20 (s, 4 H, CH2); 4.92 (t, 2 H, γꢀH, J = 12.5 Hz);
6.93 (d, 2 H, δꢀH, J = 12.5 Hz); 7.10 (d, 2 H, βꢀH, J = 12.5 Hz).
1H NMR (CDCl3), δ: 2.48 (s, 3 H, NMe); 2.88 (s, 12 H, NMe2);
3.40 (s, 4 H, CH2); 4.95 (t, 2 H, γꢀH, J = 12.5 Hz); 6.70 (d, 2 H,
B. Reagent 6 (0.49 g, 2.8 mmol) was added dropwise to a
stirred solution of dinitrile 7b (0.2 g, 0.93 mmol) in [bmim]BF4
(0.625 g, 2.7 mmol). The reaction mixture was stirred at

Crossꢀconjugated diamino ketones and nitriles
Russ.Chem.Bull., Int.Ed., Vol. 58, No. 2, February, 2009
321
70—75 °C for 4 h, kept for a day, and concentrated in vacuo.
Water (5 mL) was added to the residue and the precipitate was
filtered off, washed with water and ether, and dissolved in CHCl3
(50 mL). The solution was kept over SiO2 (L 40/100, 0.4 g) for a
day. The silica was separated and washed with CHCl3. Concenꢀ
tration gave dinitrile 5b (0.15 g, 43%), which was identical with
that described above.
9. L. A. Shvedova, Yu. E. Borisevich, A. S. Tatikolov, V. A.
Kuz´min, Zh. A. Krasnaya, Izv. Akad. Nauk SSSR, Ser. Khim.,
1983, 1421 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl.
Transl.), 1983, 32, 1290].
10. Zh. A. Krasnaya, E. O. Tret´yakova, S. G. Zlotin, Mendeleev
Commun., 2006, 326.
11. Ch. Zhang, H. R. Fetterman, W. Steier, J. Michael, US Pat.
63489, 92 B 1, Feb. 19, 2002, G 02F 1/00.
12. G. Koeckelberghs, S. Sioncke, T. Verbiest, A. Persoons,
C. Samyn, Polymer, 2003, 44, 3785.
References
13. A. V. Kulinich, N. A. Derevyanko, A. A. Ishchenko, Izv.
Akad. Nauk, Ser. Khim., 2005, 2726 [Russ. Chem. Bull., Int.
Ed., 2005, 54, 2820].
14. A. A. Ishchenko, A. V. Kulinich, S. L. Bondarev, V. N.
Knyukshto, J. Phys. Chem. A, 2007, 111, 13629.
15. Zh. A. Krasnaya, T. S. Stytsenko, Izv. Akad. Nauk SSSR,
Ser. Khim., 1983, 850, 855 [Bull. Acad. Sci. USSR, Div. Chem.
Sci. (Engl. Transl.), 1983, 32, 776, 780].
16. Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof´ev, V. F.
Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1973, 2008
[Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.),
1973, 22].
17. Yu. V. Sinyakov, D. N. Sidorin, N. V. Baikova, L. N.
Kryukov, Zh. Obshch. Khim., 1990, 60, 1931 [J. Gen. Chem.
USSR (Engl. Transl.), 1990, 60].
1. Zh. A. Krasnaya, A. S. Tatikolov, Izv. Akad. Nauk, Ser. Khim.,
2003, 1555 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1641].
2. Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof´ev, V. A.
Petukhov, V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser.
Khim., 1976, 595 [Bull. Acad. Sci. USSR, Div. Chem. Sci.
(Engl. Transl.), 1976, 25, 577].
3. Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof´ev, V. F.
Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 116
[Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1988,
27, 399].
4. Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof´ev, V. F.
Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 1362
[Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1980,
29, 980].
5. Zh. A. Krasnaya, T. S. Stytsenko, B. M. Uzhinov, S. A.
Krashakov, V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser.
Khim., 1983, 2084 [Bull. Acad. Sci. USSR, Div. Chem. Sci.
(Engl. Transl.), 1983, 32, 1882].
18. L. A. Shvedova, A. S. Tatikolov, Zh. A. Krasnaya, Khim.
Vys. Energ., 2009, 43, 160 [High Energy Chem. (Engl. Transl.),
2009, 43, No. 2].
19. L. A. Shvedova, A. S. Tatikolov, Zh. A. Krasnaya, A. R.
Bekker, V. A. Kuz´min, Izv. Akad. Nauk SSSR, Ser. Khim.,
1988, 61 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl.
Transl.), 1988, 37, 52].
6. L. A. Shvedova, A. S. Tatikolov, V. A. Kuz´min, Zh. A.
Krasnaya, A. R. Bekker, Dokl. Akad. Nauk SSSR, 1984, 276,
654 [Dokl. Phys. Chem. (Engl. Transl.), 1984, 276, 475].
7. L. A. Shvedova, A. S. Tatikolov, A. P. Darmanyan, V. A.
Kuz´min, Zh. A. Krasnaya, Dokl. Akad. Nauk SSSR, 1984,
276, 164 [Dokl. Phys. Chem. (Engl. Transl.), 1984, 276, 398].
8. L. A. Shvedova, Yu. E. Borisevich, A. S. Tatikolov, V. A.
Kuz´min, Zh. A. Krasnaya, Izv. Akad. Nauk SSSR, Ser.
Khim., 1983, 819 [Bull. Acad. Sci. USSR, Div. Chem. Sci.
(Engl. Transl.), 1983, 32, 747].
20. L. A. Shvedova, A. S. Tatikolov, V. I. Sklyarenko, Zh. A.
Krasnaya, Int. J. Photoenergy, 2005, 7, No. 3, 125.
Received July 31, 2008;
in revised form November 28, 2008