Synthesis and investigation of new organophosphorus dyes of green and red luminescence

Article abstract of DOI:10.1134/S1070363208030080

On the basis of amino derivatives of N-phenylnaphthalimide, naphthoylenebenzimidazole, benzanthrone, and phenalenone new phosphorus-containing luminophores containing phosphonomethyl and phosphazo groups in their structures were synthesized. Luminiscence spectrum and excitation characteristics of compounds obtained were studied. Some of the synthesized substances were proposed for application as effective laser dyes for green and red spectral regions with a wide range of retuning.

Full text of DOI:10.1134/S1070363208030080

ISSN 1070-3632, Russian Journal of General Chemistry, 2008, Vol. 78, No. 3, pp. 383–391. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © E.E. Nifant’ev, S.P. Belov, I.V. Komlev, V.A. Petukhov, M.A. Semenov, G.A. Mezentseva, M.A. Tavrizova, O.V. Ponomareva, 2008,
published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 3, pp. 400–407.
Synthesis and Investigation of New Organophosphorus Dyes
of Green and Red Luminescence
E. E. Nifant’eva, S. P. Belova, I. V. Komleva, V. A. Petukhovb, M. A. Semenovb,
G. A. Mezentsevaa, M. A. Tavrizovaa, and O. V. Ponomarevaa
aMoscow Pedagogical State University, Nesvizhskii per., 3, Moscow 119021 Russia
e-mail: chemdept@mtu-net.ru
bLebedev Physical Institute, Russian Academy of Sciences, Leninskii prospect, 53, Moscow 119991 Russia
e-mail: petukhov@sci.lebedev.ru
Received July 13, 2007
Abstract–On the basis of amino derivatives of N-phenylnaphthalimide, naphthoylenebenzimidazole,
benzanthrone, and phenalenone new phosphorus-containing luminophores containing phosphonomethyl and
phosphazo groups in their structures were synthesized. Luminiscence spectrum and excitation characteristics of
compounds obtained were studied. Some of the synthesized substances were proposed for application as
effective laser dyes for green and red spectral regions with a wide range of retuning.
DOI: 10.1134/S1070363208030080
In continuation of previous studies in the field of
the chemistry of phosphorus-containing organic dyes
[1–5. we undertook a synthesis and study of spectral
luminescence properties of new luminophores
luminescing in green and red regions of spectrum and
having characteristics required for practical
application. The studied compounds possess a
investigations were not systematic. These publications
practically lacked the data on spectral luminescence
characteristics of compounds obtained. We regard as
interesting patent publications on the synthesis of
phosphorus-containing dyes undertaken in connection
with the research of new fluorescent substrates for
phosphatases in biochemical investigations [10] and
development of effective antiviral preparations with
diminished toxicity [11].
common
structural feature: most of them are
derivatives of peri-indenones or their aza-analogs.
Some syntheses of phosphorylated perinaphthin-
denones were reported [6–11] (mainly, derivatives of
phenalenone and benzanthrone), but the published
Here we describe a group of novel phosphorus-
containing dyes. Structural formulas of the synthesized
compounds are shown on the scheme below.
383

384
NIFANT’EV et al.
We used as basic compounds amino derivatives of
reactions: (a) Kabacnik – Filds, (b) Kirsanov, in
Horner and Edinger modification [12], and (c) Appel
[13]. Various modes of phosphorylation are shown
with amine Ia as an example.
N-phenylnaphthalimide (I), naphthaylenebenzimida-
zole (II), benzanthrone (III) and phenalenone (IV).
For the phosphorylation we used the following
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SYNTHESIS AND INVESTIGATION OF NEW ORGANOPHOSPHORUS DYES
385
Other compounds have been obtained along the
same schemes under commonly applied conditions that
have been adjusted for each group and are described in
Experimental.
the luminophores studied by us proceeded selectively
and with higher yield compared with the use of
dibromophosphorane, leading to formation of dyes
containing phosphazo groups.
The physicochemical characteristics of the obtained
dyes are compiled in Table 1. This table contains also
the properties of several model benzanthrone and
phenalenone amino derivatives that have been
prepared from the corresponding bromo derivatives via
nucleophilic substitution by excess of a secondary
amine under the conditions close to those described in
[14].
Purification of compounds to analytical purity was
carried out using column chromatography on silica gel
(eluent chloroform); the yields listed in Table 1 were
obtained after chromatographic purification.
Reaction progress and purity of compounds
obtained were monitored by TLC in several azeotropic
eluting systems differing by polarity that we had
earlier suggested [21] for separation and identification
of organophosphorus compounds of various types.
Note that in all the cases the synthesized dyes were
featured by high chromatographic mobility and
solubility in organic liquid and polymeric media as
compared with the corresponding parent luminophores.
Various phosphorus-containing fragments
introduced into molecules of dyes are differently
manifested in electronic spectra of the synthesized
compounds. In the spectra of dyes with
aminophosphonate group the absorption and
luminescence bands suffer a small blue sfuft as
compared with the parent compounds induced
In the 31P NMR spectra of the synthesized
phoshonomethylated derivatives single signals existed
in the region typical for dialkyl(α-aminoalkyl)
phosphonates (21 to 23 ppm) [1]; signals of phosphazo
compounds were registered in a region characteristic
of triphenylphosphazoarenes (7 to 10 ppm) [15].
Certain features of the synthesis of each group
compounds should be mentioned. While the
Kabachnik–Filds reaction proceeds successfully with a
sufficiently high yield for the dyes of all types at
heating in dioxane or o-xylene, or with
dialkylphosphite excess, the synthesis of compounds
containing phosphazo group along the scheme either
(b), or (c) was successful only at boiling solutions in
chlorinated benzenes, probably due to lower basicity
of amino groups in the initial luminophores. In the
most cases the best results were obtained with 1,2,4-
trichlorobenzene as solvent, satisfactory yields were
apparently by the effect of phosphorylmethyl groups,
max
moderate acceptors [22]. The
λ
values of
absorb
compounds Ia, IIIa and IVa in ethanol are 435, 526
and 534 nm respectively (cf. with the data in Table 1).
However, intensity of luminiscence in all the cases was
higher than in the parent compounds: the fluorescence
quantum yield φ for IIIa, IIIc, and IIId equals 0.66
achieved with 1,2-dichlorobenzene,
4-amino-N-
phenylnaphthalimide (Ia) and 3-aminobenzanthrone
(IIIa) were obtained with comparable yields using
chlorobenzene. Good yields of dyes were registered
when hexachloroethane was used instead of carbon
tetrachloride.
(565 nm), 0.90 (555 nm), and 0.92 (560 nm)
max
respectively (λ
in parentheses). Increase in φ is
absorb
likely to result from steric effects of bulky
phosphorylmethyl groups restricting the rotation of
amino groups and thus reducing the probability of
nonradiation deactivation of the electronic excitation.
The presence in the molecules of dyes of
triphenylphosphazo groups, in all likelihood the
strongest donor substituents, changes considerably
electronic spectra of compounds: the absorption and
luminescence bands undergo a strong red shift, and the
Stocks shift increases significantly, up to 140 nm. For
all the synthesized iminophosphoranes an intensity of
luminescence considerably increased as compared with
the parent luminophores, apparently due both to the
steric effect of bulky triphenylphosphazene groups and
the mobility of effective partial charges along the
phosphazo bond because of the involvement of the
nitrogen lone pair in its formation. Thus, we measured
quantum yields of fluorescence for some phosphazo
While Horner–Ediger reaction has been used for
preparation of various phosphazo compounds for
relatively long period [16-18], the Appel reaction is
less known despite its interesting recent applications
[19-20]. Synthesis of dyes along the Appel scheme is
smooth enough at short (few minutes) boiling of the
reaction mixture in a preliminary heated oil bath till
the disappearence of the initial amino compound
(TLC monitoring). In all cases the 31Р NMR spectra
revealed the formation of triphenylchloro-
methylphosphonium chloride (δP = –22.1 ppm), the
side product in all systems containing three
components: Ph3P–CCl4–nucleophile. The mechanism
of its formation was considered in detail in [13, 20].
Note that the Appel reaction applied to the synthesis of
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NIFANT’EV et al.
Table 1. Physicochemical and spectral characteristics of synthesized organophosphorus dyes (numbers correspond to the
scheme)
λmabasxorb , nm
Elemental analysis
(ε × 10−4)
found, %
calculated, %
Comp.
no.
mp,
°С
Formula
C
H
N
P
C
H
N
P
242–243 C23H23N2O5P 72.4 63.21 5.35 6.22 6.84 63.01 5.29 6.39 7.06 411
258–259 C23H27N2O5P 76.3 67.25 5.11 5.27 5.73 67.70 5.29 5.44 6.02 410
124–125 C25H19N2O5P 69.5 48.95 3.05 4.35 4.89 49.19 3.14 4.58 5.07 360
450
418
380
424.5
414
23.06
21.45
Ib
Ic
Id
384
162–163 C24H23N2O5P 74.8 63.78 5.02 6.11 6.53 64.00 5.15 6.22 6.88 376
280–281 C36H25N2O2P 48.7 79.60 4.74 4.92 4.81 79.82 4.59 5.10 5.65 430
432
450
381
445
Ie
If
9.08
(1.84) (2.02) (2.64)
169–170 C51H37N2O2P 45.5 79.67 4.82 7.25 3.91 79.67 4.85 7.28 4.03 435 450 447
(2.46) (1.80) (2.24)
Ig
262–263 C40H33N2O2P 64.2 78.65 5.51 4.51 5.03 79.45 5.50 4.63 5.13 432
451
442
10.33
Ih
Ii
295–296 C40H33N2O2P 76.2 78.89 5.45 4.56 5.01 79.45 5.50 4.63 5.13 430
455
445
(2.70) (3.60) (2.44)
235–236 C41H34N2O6P2 37.2 70.41 4.97 3.27 8.36 69.09 4.81 3.93 8.70 430
450
445
Ij
(2.56) (2.20) (2.40)
258–259 C41H35N2O2P 48.2 79.10 5.41 3.10 4.95 79.59 5.70 3.20 5.00 431
450.5
495
448.5
493
Ik
258–259 C36H24N3OP
215–217 C21H17NO2
34.6 79.16 4.25 7.52 5.06 79.25 4.43 7.70 5.68 485
10.57
IIb
(2.07) (2.44) (2.12)
85
79.75 5.52 4.12
–
79.98 5.43 4.44
–
432
445
444
–
IIIb
(3.82)
141–142 C32H37NO4P
38
73.40 6.42 2.52 5.73 73.22 6.55 2.60 5.86 469
497
496
495
482
21.30
27.32
IIIc
IIId
161–162 C32H35N2O4P 31.5 70.63 6.40 5.25 5.83 70.83 6.50 5.16 5.71 468
261–262 C35H24NOP
108–109 C15H13NO
60
83.08 4.66 3.20 5.67 83.15 4.79 2.77 6.13 495
80.17 5.36 6.12 80.69 5.87 6.27 463
61.80 5.78 3.95 8.70 62.60 5.84 4.06 8.97 473
528
497
539
502
7.85
IIIf
68
69
–
–
–
IVb
87–88
C18H20NO4P
527
500
524
497
21.43
20.71
IVc
IVd
142–143 C24H24NO4P
58.9 68.11 5.68 3.25 7.10 68.40 5.74 3.32 7.35 468.5
164–165 C24H33N2O4P 28.9 64.15 7.47 6.02 6.50 64.85 7.48 6.30 6.97 470.3
498.5
496
513
20.16
IVe
IVf
149–150 C31H22NOP
58
81.16 4.72 2.97 6.52 81.74 4.87 3.08 6.80 495
555
(0.93) (1.06)
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SYNTHESIS AND INVESTIGATION OF NEW ORGANOPHOSPHORUS DYES
387
Fig. 1. Adsorption (1, 2) and fluorescence spectra (3, 4) of 3-phosphazophenalenone (IVе): (1, 3) in toluene, (2, 4) in ethanol.
Fig. 2. Dependence of excitation energy of dye solutions in ethanol on the wavelength: (1) dye Ic; (2) dye IIIe; (3) coumarin 7;
(4) uranine; (5) cresyl violet.
compounds (in parentheses are given the values of
Figure 2 shows absorption and fluorescence spectra
of dye IVf in ethanol and toluene at 25˚С (c = 0.5×
10−4 mol l–1).
max
λ
and solvents): 0.94 (541 nm, propylene
absorb
carbonate), 0.75 (500 nm, toluene) (If); 0.78 (500 nm,
toluene), 0.88 (530 nm, propylene carbonate) (Ii); 0.92
(570 nm, toluene), 0.82 (600 nm, propylene carbonate)
(IVf).
For some of dyes with strong luminescence we
studied the possibility of their application as com-
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388
NIFANT’EV et al.
Table 2. Excitation properties of ethanol solutions of some of the synthesized compounds as compared with the known laser
dyes for green and red spectral regions at the pumping with illumination of 3d harmonic of neodimium laser
Differential
efficiency,
Retuning region, nm
Dye
λexc, nm
Еpump, mJ
Еexc, mJ (Еpump, 20 mJ)
%
Coumarin 7
524
557
542
542
530
542
676
679
640
670
668
0.25 0.12
0.25 0.06
1.2 0.6
11.6
13.6
11.2
12.7
22.0
9.2
1.24
2.58
1.61
1.63
3.9
500–565
540–580
Uranine
Ia
2.3 0.3
Ib
0.2 0.02
0.80 0.15
0.2 0.1
500–600
495–605
645–700
Ic
1.64
1.53
0.89
1.70
2.26
Id
Cresyl violet
IIIa
9.3
4.8 0,5
10.4
22.0
15.5
28.0
4.0 0,6
640–740
IIIc
0.30 0.15
0.13 0.05
IIIe
IIIea
a Pumping by second harmonic of neodymium laser on phosphate glass (527 nm).
ponents of liquid media for dye lasers. Under
identical conditions we measured principal excitation
characteristics: the excitation wave length in a broad-
band resonator, pumping energy, energy of
excitation at various pumping energies, and we
determined differential performance near the
threshold. For comparison of the studied compounds
with the existing laser dyes we measured under the
same conditions the energy of excitation for ethanol
solutions of several widely used substances regarded
as the most effective [23]. For the most effective
compounds we measured retuning curves, namely,
the dependence of excitation energy on the wave
length at the use of selective resonator. The results
are shown in Fig. 3. It is seen that the regions of
excitation wave lengths of dyes Ic and IIIc
considerably exceed the areas of retuning of other
dyes in the related spectral range. These compounds
also are no worse in efficiency than the reference
substances.
spectrum, and Ic is notably better than both
coumarine 7 and uranin. The efficiency of excitation
for this compound is above 20% in a wide range of
pumping energy and falls insignificantly in the
region of extreme pumping. Optimization of the dye
concentration and parameters of resonator, and use
of pumping with more appropriate spectrum
probably may increase its excitation efficiency. It is
of great value that the excitation wave length of this
compound (530 nm) falls into the most
“unfavorable” spectral region. It can also be noted
that the naphthalylimides studied by us can be easily
synthesized from the known parent dye Ia providing
an opportunity of their preparation in large amounts
at low cost.
Thus, the studied compounds by their
fundamental characteristics are better than the dyes
widely applied in green and red spectral regions and
thus they are promising for extensive application as
active laser media.
Among the studied benzanthrones with excitation
in the red spectral region a special attention should
be given to dye possessing triphenylphosphazenyl
substituent N=P(C6H5)3.This compound by excita-
Table 2 comprises the excitation characteristics of
the studied dyes. As seen, among the naphthalimides,
compound Ib shows excitation activity on the level
of the reference compounds in the green region of
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SYNTHESIS AND INVESTIGATION OF NEW ORGANOPHOSPHORUS DYES
389
Fig. 3. Dependence of excitation energy of dye solutions in ethanol on the pumping energy: (1) dye Ic; (2) uranine;
(3) dye IIIe; (4) cresyl violet; (5) coumarin 7.
dyes at illumination with mercury lamp. The results of
measuring фку listed below.
tion energy and differential efficiency is better than
cresyl violet commonly used шт this region (λexc= 670
nm): at equal pumping the excitation energy of
IIIe is 1.5 times higher (see Fig. 3).
It was showт that photostability of the phosphorus-
containing dyes is higher as compared with the parent
compounds. Dye Ic, the most effective in the green
region, by its photostability is no worse than coumarin,
althouth it is inferior to uranin 7. In the red region dye
IIIe is much more stable than cresyl violet.
An important characteristics of the dyes is their
photostability, therefore we carried out comparative
measurement of the rate of photo-damage of the best
Thus, we synthesized new phosphorus-containing
organic dyes based on the available luminophores;
their spectroluminiscence and excitation characteristics
were measured. It is shown that the synthesized
compounds are effective luminescent substances.
Some of these newly synthesized compounds by their
excitation characteristics exceed the laser dyes
commonly used in the green and red spectral regions,
and can be recommended as the components of active
laser media.
Dye
Ia
Ic
If
IIIa
IIIc
IIIe
Coumarin 7
Uranine
Cresyl violet
Photodecomposition period, h
2.3
4.9
5.2
4.8
7.6
10.7
5.1
14
0.2
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390
NIFANT’EV et al.
EXPERIMENTAL
column with silica gel L 100/160 (eluent chloroform),
Rf 0.72 (I), 0.39 (II), 0.64 (III). Compounds Ib, IIIc
and IVc-IVe were prepared similarly. Compounds Id
and Ie were synthesized with equimolar amount of the
corresponding phosphite in o-xylene at 3 h boiling.
3-(Triphenylphosphazo)benzanthrone (IIIe). a.
A mixture of 0.61 g of IIIa, 0.66 g of tri-
phenylphosphine and 0.38 g of carbon tetrachloride in
30 ml of о-dichlorobenzene was refluxed for 10 min in
a preheated oil bath to disappearance of the parent
amine (TLC monitoring). The mixture was filtered and
after chromatography of the filtrate on a column with
L 40/100 silica gel (eluent chloroform) 0.48 g of IIIe
was obtained as dark-cherry crystals. Rf 0.48 (I), 0.72
(II), 0.44 (III). Phosphazo compounds Ie-Ik, IIb and
IVf were obtained similarly.
b. To a solution of 1.11 g of triphenyldibromo-
phosphorane [12] in 30 ml of chlorobenzene was
added at stirring 0.61 g of IIIa and 0.5 g of
triethylamine, the mixture was refluxed for 7 h,
filtered, and the filtrate was passed through a column
with silica gel L 40/100 (eluent chloroform). Yield
59%; the product was identical to that obtained by
method a by its adsorpton spectra, Rf, and mp of a
mixed sample.
31
The P NMR spectra were taken from solutions in
chloroform on a Bruker WP-80SY instrument,
operating frequency 32.4 МMHz, reference compound
85% H3PO4. The UV spectra were measured on a
Specord UV-VIS spectrophotometer, the luminescence
spectra were registered on an installation assembled on
the basis of MDR-3 monochromator. Excitation
characteristics were measured at pumping with third
harmonics of Nd-laser (351 nm), transverse pumping.
In some cases we used pumping with second
harmonics of Nd-laser. The excitation threshold and
differential efficiency were measured using a short
nonselective resonator 3 cm in length. For the most
effective dyes retuning curves were measured, and the
range of wavelength retuning was determined. The
retuning was carried out using selective prisms placed
inside the resonator. The rate of photo-damage of the
ethanol solutions of dyes was measured at illumination
with mercury lamp DRT-220 at the distance of 10 cm.
The solutions were placed into the rectangular cells of
fused glass 1 cm thick, initial optical density in the
maximum of adsorption spectrum was taken at equal to
0.3. The illumination was interrupted intermittently,
and optical density of solutions was measured. As the
period of photo-damage was taken the time of 2.71-
fold decrease in optical density at the maximum of
adsorption.
ACKNOWLEDGMENTS
This work was financially supported by the grant
of Russian Federation for supporting young Russian
scientists and advanced scientific schools of Russian
Federation (no. NSh-5515.2006.3), and by the grant of
Russian Foundaton for Basic Research (Project no. 05-
02-17448).
Thin layer chromatography was carried out with
Silufol UV-366 plates from Cavalier (Czech republic)
by ascending method in the following systems:
chloroform–ethanol (10:1) (I), chloroform– acetone
(331:169) (II), benzene–dioxane (88:12) (III) under
conditions like those described in [21].
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