Sandwich complexes of yttrium, neodymium, gadolinium, and dysprosium with meso-trans-di(hexadecyl)-tetrabenzoporphyrin and phthalocyanine fragments. Synthesis and spectral properties

Article abstract of DOI:10.1134/S1070363212040275

Sandwich-type asymmetric complexes of yttrium, neodymium, gadolinium, and dysprosium were synthesized by the reaction of the corresponding meso-trans-bis(hexadecyl)tetrabenzoporphyrinates with dilithium phthalocyianine. Spectral properties of these compou

Full text of DOI:10.1134/S1070363212040275

ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 4, pp. 764–769. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © N.E. Galanin, G.P. Shaposhnikov, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 4, pp. 681–687.
Sandwich Complexes of Yttrium, Neodymium,
Gadolinium, and Dysprosium with meso-trans-Di(hexadecyl)-
tetrabenzoporphyrin and Phthalocyanine Fragments.
Synthesis and Spectral Properties
N. E. Galanin and G. P. Shaposhnikov
Ivanovo State University of Chemical Engineering, pr. Engel’sa 7, Ivanovo, 153000 Russia
e-mail: ttoc@isuct.ru
Received January 20, 2012
Abstract— Sandwich-type asymmetric complexes of yttrium, neodymium, gadolinium, and dysprosium were
synthesized by the reaction of the corresponding meso-trans-bis(hexadecyl)tetrabenzoporphyrinates with
dilithium phthalocyianine. Spectral properties of these compounds were investigated.
DOI: 10.1134/S1070363212040275
Sandwich complexes of rare earth elements with
tetrapyrrole ligands are stable compounds of unique
structure, attracting both theoretical and practical
interest. They can be used as materials for sensor
systems [1, 2], optical limiters [3], electrochromic
materials [4], materials for the sensors of ionizing
radiation [5] and in other areas.
This communication concerns the synthesis and
spectral properties of the sandwich complexes of
yttrium (I), neodymium (II), gadolinium (III), and
dysprosium (IV) containing fragments of the meso-
trans-bis(hexadecyl)tetrabenzoporphyrin and phthalo-
cyanine. The starting compound for their synthesis
were meso-trans-bis(hexadecyl)tetrabenzoporphyrin (V)
obtained by the interaction 1-[1-oxo-1H-isoindol-3-yl)me-
thyl]isoindolin-3-one (VI) synthesized by the method
[13] with stearic acid and zinc oxide, followed by
demetallation of the formed zinc meso-trans-bis(hexa-
decyl)tetrabenzoporphyrinate (VII) with sulfuric acid.
By boiling solution of the porphyrin (V) in DMF with
an excess of yttrium, neodymium, gadolinium, or dyspro-
sium chloride the corresponding lanthanide complexes
VIII–XI were obtained in accordance with Scheme 1.
At present there are numerous methods of synthesis
of sandwich lanthanide complexes containing phthalo-
cyanine and porphyrin molecules [6–10]. However, the
information about the structure of such complexes
containing phthalocyanine and tetrabenzoporphyrin
molecules is very limited [11, 12], and the information
on the structures that combine the meso-trans-dialkyl-
tetrabenzoporphyrin and phthalocyanine fragments has
not been found in the literature.
Scheme 1.
C16H33
C16H33
C16H33
O
N
N
N
HN
N
N
N
N
N
N
H35C17COOH,
ZnO
MCl3
H2SO4
Cl−M
Zn
N
N
NH
NH
O
C16H33
VIII−XI
C16H33
C16H33
VII
VI
V
M = Y (VIII), Nd (IX), Gd (X), Dy (XI).
764

SANDWICH COMPLEXES OF YTTRIUM
765
The formation of complexes was monitored spectro-
photometrically by disappearance of the bands at 608
and 663 nm characteristic of ligand V in the electron
absorption spectrum of the reaction mixture and the
appearance of bands at 627–629 nm corresponding to
the Q-bands of the complexes VIII–XI. Because of the
large ionic radii of the metals the reaction proceeds
relatively slowly and is completed in 16 h.
1462 cm–1 reflecting vibrations of the C–N bonds.
Splitting of these bands points to the non-equivalence
of chromophores [14, 15]. The position of the charac-
teristic bands in the IR spectra of compounds I– IV
depends on the ionic radius of the metal (RM). Table 1
lists the vibration frequencies of the respective bonds.
As follows from these data, the increase in the ionic
radius of the metal (at the coordination number equal
to eight) leads to a shift of the bands of the N–M vibra-
tions and vibrations of the radical fragment of phthalo-
cyanine to the low-frequency region (Figs. 1a, 1b).
Compounds VIII–XI were isolated after diluting
the reaction mixture with water followed by extraction
with chloroform. The organic phase in each case was
washed with water, the solvent was distilled off, and
the residue was washed with 80% ethanol and dried.
As to the positions of the bands corresponding to
the C–N vibrations in phthalocyanine and porphyrin
chromophores, we did not find any relationship
between their position and the ionic radius of the metal.
The sandwich complexes I–IV were synthesized in
accordance with Scheme 2 by the reaction of dilithium
phthalocyanine obtained by heating phthalonitrile in 1-
hexanol in the presence of lithium metal, with the
compounds VIII–XI in the same solvent at boiling the
reaction mixture for 6 h.
1H NMR spectrum of compound III (Table 2)
contains four groups of signals. In the weak field at
9.23 ppm there is a singlet corresponding to the resonance
of the two meso-protons of the porphyrin fragment.
Two singlets at 7.86 and 7.79 ppm correspond to the
resonance of the 32 protons of benzene rings and iso-
indole fragments of phthalocyanine (Pc) and tetrabenzo-
porphyrin (TBP), respectively. In the strong field there
is a multiplet at 2.19 ppm corresponding to the resonance
of 60 protons of the methylene groups of alkyl substitu-
ents, and, finally, a singlet at 1.27 ppm corresponding
to the resonance of 6 protons of terminal methyl
In each case, at the end of the process the alcohol
was distilled off at a reduced pressure, the reaction
mixture was treated with 10% acetic acid, the
precipitate formed was washed with hot 80% ethanol
and dried. Compounds I–IV were purified by column
chromatography. Their composition and structure was
confirmed by elemental analysis, vibrational, 1H NMR,
and electron spectroscopy.
1
groups. The H NMR spectra of complexes I, II, IV
Vibrational spectra of compounds I–IV, as ex-
pected, are similar to each other. Each contains intense
bands in the region of 2956–2854 cm–1 corresponding
to the CH bond vibrations of the alkyl substituents,
characteristic bands in the region 856–879 cm–1 cor-
responding to the N–M vibrations, the bands in the
region 1361–1383 cm–1, typical of the radical fragment
of phthalocyanine (Pc•), and the band at 1448–
are similar in nature to the spectrum of compound III.
The signals positions are given in Table 2.
Due to the paramagnetic nature of the lanthanides,
the proton signals are significantly shifted. Thus, the
signals of protons in the meso-positions of the por-
phyrin macrocycle are shifted upfield by 0.55–2.77 ppm
compared with their position (11.12 ppm) in the
Scheme 2.
N
N
N
N
C16H33
C16H33
N
CN
CN
N
N
N
N
H13C6OH,
H13C6OLi
VIII−XI
Li
Li
N
M
N
N
N
N
N
N
N
N
N
N
I−IV
M = Y (I, VIII), Nd (II, IX), Gd (III, X), Dy (IV, XI).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012

766
GALANIN, SHAPOSHNIKOV
Table 1. IR spectral parameters of complexes I–IV, ν, cm–1
Comp. no.
M
Y
rM, nm
0.116
0.125
0.115
0.127
N–M
856
879
862
883
Pc•
C–N
1364
1383
1361
1373
1443, 1446
1452, 1461
1453, 1462
1448, 1465
I
Nd
Gd
Dy
II
III
IV
Table 2. 1H NMR spectral parameters of compounds I–IV in CDCl3, δ, ppm
Comp. no.
M
meso-Н
9.19 s
Рс-Н
7.84 s
TBP-Н
СН2
СН3
Y
7.76 s
1.26 m
1.29 m
2.19 m
1.43 m
0.88 s
0.89 s
1.27 s
0.95 s
I
Nd
Gd
Dy
8.35 s
7.87–7.82 m
7.86 s
7.76–7.68 m
7.79 s
II
9.23 s
III
IV
10.57 s
8.08–7.88 m
7.79–7.62 m
spectrum of the zinc complex VII. The signals of the
protons of the benzene rings of the tetrabenzopor-
phyrin chromophores, as well as of alkyl substituents,
are in the same areas as in the spectrum of compound
VII, except for complex III: in the spectrum of the
latter the proton signals of alkyl substituents are shifted
downfield by 0.5–0.9 ppm.
which is more intense than the band at 666 nm. The
intensity ratio of the two latter becomes equal to
1:0.93. This fact indicates the transformation of I in
the presence of reducing compound into the anionic
“blue” form. In both cases, the bands at 434 and 420 nm
correspond to the tetrabenzoporphyrin B bands, and at
349 and 345 nm, to the B bands of phthalocyanine.
Among the most important characteristics of the
sandwich-type complexes the data of electron absorp-
tion spectroscopy should be mentioned. The electronic
spectroscopy is the simplest and most informative
method of identifying the “green” and “blue” forms of
sandwich compounds.
The electron absorption spectra of the gadolinium
complex III (Fig. 3) are similar by their characteristics
to the spectrum of compound I. We noted only a 5–
7 nm red shift of the bands in the Q region and a
slightly smaller splitting of Q band in the chloroform
solution (Fig. 3, curve 1). In addition, the intensity of
the Q bands increases with respect to B bands of
tetrabenzoporphyrin chromophore located in the same
area as in the spectrum of the complex I.
The electron absorption spectrum of complex I
solution in chloroform (Fig. 2, 1) is characterized by a
strong band with the maximum at 665 nm and a less
intense band at 687 nm, evidencing the presence of the
phthalocyanine radical fragment, and the ratio of their
intensities is equal to 1.46: 1. Thus, complex I exists in
chloroform mainly in the neutral-radical “green” form.
Replacing chloroform by DMF with the addition of 1%
hydrazine hydrate as reducing agent leads to certain
changes (Fig. 2, curve 2). The band with maximum at
687 nm disappears while a band at 617 nm appears,
The electron absorption spectra of the complex II
with neodymium (Fig. 4) differ markedly from the
spectra of the compounds I and III by the character
and position of the maxima of absorption bands. In the
spectra of complex II the resonance splitting of the Q
band is significantly reduced, while its relative inten-
sity increases. The bands at 433 and 416 nm cor-
responding to the B bands of tetrabenzoporphyrin are
(a)
(b)
rM, nm
rM, nm
Fig. 1. Dependence of the position of the bands (a) N–M and (b) (Pc•) on the metal ionic radii.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012

SANDWICH COMPLEXES OF YTTRIUM
767
D
D
λ, nm
Fig. 2. Electron absorption spectra of compound I: (1) in
CHCl3, (2) in DMF +1% of NH2NH2·H2O.
λ, nm
Fig. 3. Electron absorption spectra of compound III: (1) in
CHCl3, (2) in DMF +1% of NH2NH2·H2O.
less resolved, while the band at 478 nm in the
spectrum in chloroform (Fig. 4, curve 1) corresponding
to electronic transitions in the phthalocyanine radical
fragment becomes more pronounced. These combined
facts suggest a significantly stronger interaction be-
tween the porphyrin and phthalocyanine chromophores.
B bands vs the ionic radii of lanthanide complexes I–
IV is shown in Fig. 6.
Perhaps, the unusual properties of the complexes I–
IV should be attributed to the increase in the distortion
of the planar structure of porphyrin fragments with the
decreasing distance between them and the fragments
of phthalocyanine caused by the smaller ionic radius
of the metal, resulting in a weakening of the π–π
interaction between the chromophores.
An even stronger interaction of these chromophores
was observed in the dysprosium complex IV. The
resonance splitting of Q band is significantly reduced
in the spectrum of its solution in chloroform (Fig. 5,
curve 1), while in the spectrum in DMF with the
addition of hydrazine hydrate (Fig. 5, curve 2) it
increases. The band at 455 nm in the spectrum in
chloroform becomes even more pronounced that shows
the radical nature of the phthalocyanine fragment. On
the contrary, the B bands of porphyrin chromophore
become even less intense.
EXPERIMENTAL
The electron absorption spectra of the compounds
were measured on a Hitachi UV-2001 spectrophoto-
1
meter, the H NMR spectra (internal reference TMS)
on a Bruker Avance-500 instrument, the IR spectra on
an Avatar 360 FT-IR spectrophotometer in the region
of 400–4000 cm–1, from the films on TlI glass, the mass
Thus, the spectral properties of the synthesized
complexes to a large extent depend on the nature of the
metal present in their composition. It is interesting to
note that judging from the electron absorption spectra
the interaction between the phthalocyanine and
tetrabenzoporphyrin chromophores is stronger in the
case of complexes with neodymium II and dysprosium
IV, although the ionic radii of these lanthanides are
large, 0.125 and 0.127 nm respectively. On the
contrary, the interaction of the phthalocyanine and
porphyrin fragments is weaker in the complexes with
gadolinium III and yttrium I, whose ionic radii are
much smaller: 0.115 and 0.116 nm, respectively.
D
A consequence of increasing interaction between
the chromophores is a decrease in the relative in-
tensities of the bands corresponding to tetrabenzo-
porphyrin B bands. The plot of intensity ratio of Q and
λ, nm
Fig. 4. Electron absorption spectra of compound II: (1) in
CHCl3, (2) in DMF +1% of NH2NH2·H2O.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012

768
GALANIN, SHAPOSHNIKOV
rM, nm
λ, nm
Fig. 5. Electron absorption spectra of compound IV: (1) in
CHCl3, (2) in DMF +1% of NH2NH2·H2O.
Fig. 6. Dependence of the intensity ratio of Q and B bands
on the ionic radius of metal.
spectrum was recorded on a Bruker Reflex III spectro-
meter (MALDI–TOF, dithranol matrix). Elemental analysis
was performed on a FlashEA 1112 CHNS–O Analyzer.
form, CCl4, hexane, and poorly soluble in acetone.
Electron absorption spectrum (CCl4), λmax, nm (log ε):
419 (4.86), 433 (4.90), 565 (4.15), 603 (4.35), 608
1
(4.37), 616 (4.35), 663 (4.28) . H NMR spectrum
Zinc meso-trans-di(hexadecyl)tetrabenzoporphyri-
nate (VII). A mixture of 0.02 mol of compound VI,
0.04 mol of stearic acid, and 0.05 mol of zinc oxide
was heated to 320°C and kept at this temperature for
1 h, then cooled and extracted with CCl4 in a Soxhlet
apparatus. The extract was chromatographed on a
column filled with aluminum oxide of II degree of
activity by Brockmann (eluent CCl4–dioxane mixture,
2:1 by volume), collecting the main green area. Yield
3.3 g (32%). Dark-green substance, readily soluble in
benzene, chloroform, CCl4, hexane, poorly soluble in
acetone. Electron absorption spectrum (CCl4), λmax, nm
(log ε): 402 (4.59), 427 (5.02), 579 (4.03), 626 (4.50).
1H NMR spectrum (CDCl3), δ, ppm: 11.12 s (2H),
7.77–7.41 m (16H), 2.26 m (4H), 1.33 s (56H), 0.85 m
(6H). Mass spectrum, m/z: 1020 [M]+. Found, %: C
80.22; H 8.76; N 5.12. C68H84N4Zn. Calculated, %: C
79.85; H 8.28; N 5.48.
(CDCl3), δ, ppm: 5.11 s (2H), 7.78–7.43 m (16H), 2.22
m (4H), 1.30 s (56H), 0.86 m (6H), –2.35 s ( 2H).
Found, %: C 85.20; H 10.12; N 5.42. C68H86N4.
Calculated, %: C 85.13; H 9.03; N 5.84.
Complexes VIII–IX. General procedure. 0.1 mmol
of compound V was dissolved in 25 ml of DMF and
3 mmol of the corresponding metal chloride was
added. The reaction mixture was heated for 16 h at
reflux, cooled, diluted with 50 ml of water, and extracted
with 50 ml of chloroform. The extract was washed with
water, the solvent was distilled off, and the residue was
washed with 50 ml of 80% aqueous ethanol and dried.
Chloroittrium meso-trans-di(hexadecyl)tetrabenzo-
porphyrinate (VIII). Yield 0.10 g (91%), dark-green
powder, soluble in toluene, chloroform, acetone, DMF.
The electron absorption spectrum (CCl4), λmax, nm
(D/Dmax): 629 (0.30), 430 (1.00). Found, %: C 76.22;
H 8.11; N 4.99. C68H84ClN4Y. Calculated, %: C 75.50;
H 7.83; N 5.18.
meso-trans-Di(hexadecyl)tetrabenzoporphyrin (V).
0.5 g of complex VII was dissolved in 50 ml of concn.
sulfuric acid and maintained at 20°C for 2 h. The
solution was then diluted with 150 ml of water, the
precipitate formed was filtered off, washed on the filter
sequentially with 150 ml of 20% solution of ammonia
and 100 ml of water, and dried. The residue was
dissolved in CCl4 and chromatographed on a column
filled with aluminum oxide of II degree of activity by
Brockmann (eluent CCl4–dioxane, 2:1 by volume),
collecting the main green area. Yield 0.35 g (77%).
Dark-green substance, readily soluble in benzene, chloro-
Chloroneodimium meso-trans-di(hexadecyl)tetra-
benzoporphyrinate (IX). Yield 0.10 g (83%), dark-
green powder, soluble in toluene, chloroform, acetone,
DMF. The electron absorption spectrum (CCl4), λmax
,
nm (D/Dmax): 622 (0.27), 423 (1.00). Found, %: C
72.31; H 8.25; N 4.54. C68H84ClN4Nd. Calculated, %:
C 71.83; H 7.45; N 4.93.
Chlorogadolinium meso-trans-di(hexadecyl)tetra-
benzoporphyrinate (X). Yield 0.11 g (92%), dark-
green powder, soluble in toluene, chloroform, acetone,
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SANDWICH COMPLEXES OF YTTRIUM
769
DMF. The electron absorption spectrum (CCl4), λmax
,
chloroform, acetone, DMF. Electron absorption spec-
trum, λmax, nm (D/Dmax): CHCl3, 670 (0.94), 602
(0.53), 478sh, 434 (1.00), 419 (0.97). DMF + 1% of
N2H4·H2O, 683 (0.51), 624 (1.00), 433 (0.86), 418
(0.87). IR spectrum, ν, cm–1: 2956, 2867, 1572, 1520,
1462, 1453, 1361, 1297, 1227, 964, 862, 806, 767,
nm (D/Dmax): 624 (0.29), 424 (1.00). Found, %: C
71.88; H 8.17; N 4.43. C68H84ClGdN4. Calculated, %:
C 71.01; H 7.36; N 4.87.
Chlorodysprosium meso-trans-di(hexadecyl)tetra-
benzoporphyrinate (XI). Yield 0.10 g (92%), dark-
green powder, soluble in toluene, chloroform, acetone,
705. Found, %: C 74.55; H 5.13; N 9.88. C100H100
GdN12. Calculated, %: C 73.81; H 6.19; N 10.33.
·
DMF. The electron absorption spectrum (CCl4), λmax
,
nm (D/Dmax): 628 (0.28), 427 (1.00). Found, %: C
71.54; H 7.89; N 4.19. C68H84ClDyN4. Calculated, %:
C 70.69; H 7.33; N 4.85.
meso-trans-Di(hexadecyl)tetrabenzoporphyrin–
dysprosium–phthalocyanine (IV). Yield 60 mg
(42%), dark-green powder, soluble in toluene,
chloroform, acetone, DMF. Electron absorption spec-
trum, λmax, nm (D/Dmax): CHCl3, 662 (0.97), 634
(0.48), 455 (0.300), 330 (1.00). DMF + 1% of
N2H4·H2O, 684 (0.42), 621 (0.93), 413 sh, 331 (1.00).
IR spectrum, ν, cm–1: 2950, 2877, 1465, 1448, 1422,
1373, 1321, 1115, 1063, 883, 768, 731, 498. Found,
%: C 74.87; H 6.22; N 9.74. C100H100DyN12. Calcu-
lated, %: C 73.58; H 6.17; N 10.30.
Sandwich complexes of type I–IV. General
procedure. To a solution of dilithium phthalocyanine
prepared by boiling 0.3 g of phthalonitrile in 20 ml of
1-hexanol in the presence of 0.05 g of lithium metal
for 2 h, was added 0.10 g of metalloporphyrin VIII–
IX. The reaction mixture was heated at reflux for 6 h,
and then alcohol was distilled off in a vacuum, the
reaction mixture was treated with 50 ml of 10%
solution of acetic acid, washed with 30 ml of hot 80%
ethanol, and dried. The residue was dissolved in chloro-
form and chromatographed on a column filled with
aluminum oxide of II degree of activity by Brockmann
(eluent chloroform), collecting the main green area.
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meso-trans-Di(hexadecyl)tetrabenzoporphyrin-
ittrium-phthalocyanine (I). Yield 55 mg (38%), dark-
green powder, soluble in toluene, chloroform, acetone,
DMF. The electron absorption spectrum, λmax, nm
(D/Dmax): CHCl3, 687 (0.30), 665 (0.44), 602 (0.23)
and 434 (0.62), 420 (0.64), 345 (1.00). DMF + 1% of
N2H4·H2O – 666 (0.34), 617 (0.37), 432 (0.78), 417
(0.82), 349 (1.00). IR spectrum, ν, cm–1: 2955, 2867,
1578, 1524, 1446, 1443, 1364, 1163, 1114, 856, 763,
639, 556. Found, %: C 78.01; H 6.17; N 10.12. C100H100·
N12Y. Calculated, %: C 77.05; H 6.47; N 10.78.
meso-trans-Di(hexadecyl)tetrabenzoporphyrin–
neodimium–phthalocyanine (II). Yield 57 mg (40%),
dark-green powder, soluble in toluene, chloroform,
acetone, DMF. Electron absorption spectrum, λmax, nm
(D/Dmax): CHCl3, 677 (0.65), 635 (0.34), 478 (0.26),
433 (0.32), 416 (0.34), 320 (1.00). DMF + 1% of N2H4·
H2O, 670sh, 631 (0.88), 430 (0.21), 416 (0.28), 331
(1.00). IR spectrum, ν, cm–1: 2944, 2854, 1722, 1661,
1532, 1461, 1452, 1383, 1279, 1134, 1082, 951, 879,
761, 720, 547. Found, %: C 74.88; H 7.15; N 9.76.
C100H100N12Nd. Calculated, %: C 74.41; H 6.24; N 10.41.
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meso-trans-Di(hexadecyl)tetrabenzoporphyrin–
gadolinium–phthalocyanine (III). Yield 58 mg
(41%), dark-green powder, soluble in toluene,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012