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6Порфиразины_ МаКрОГ8Т8рОЦМКЛЬ1_Статья
Porphyrazines http://macrDhetBrocycles.lsuc:l.m Paper
Synthesis and Characterization of Some Five-Coordinated Tetraazaporphyrin and Phthalocyanine Manganese(III) Complexes
Ekaterina N. Ovchenkova,a Michael Hanack,b and Tatyana N. Lomovaa@
aInstitute of the Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia bUniversität Tübingen, Institut für Organische Chemie, Morgenstelle 18, 72076 Tübingen, Germany @Corresponding author E-mail: [email protected]
Soluble pentacoordinated manganese(III) complexes with substituted tetraazaporphyrins (TAPs) containing m-trifluoromethylphenyl, p-tert-butylphenyl groups and phthalocyanines (Pcs) containing m-trifluoromethylphenyl, m-trifluoromethylphenoxy and 3,5-di-tert-butylphenoxy groups have been synthesized either by direct metallation of macrocycles (TAPMn, 1a, and PcMns, 3a and 4a) or by template cyclotetramerization of the corresponding fumaronitrile (TAPMn, 2a) andphthalonitrile (PcMn, 5a) and characterized in details.
Keywords: Phthalocyanines, tetraazaporphyrins, manganese complexes, synthesis, spectroscopic properties.
Introduction
At present, the practical uses of porphyrins (P), tetraazaporphyrins (TAP), phthalocyanines (Pc) and their metal complexes are intensively developing.[1,2] The steady interest in TAPMn and PcMn compounds has grown up after it was found that the manganese complexes are active catalysts in oxidation processes as the iron derivatives are.[3] Therefore, when applying PMns and PcMns as catalysts, it is reasonable to expect some selectivity in oxidation of hydrocarbons, which can be achieved and controlled by optimization of the reaction conditions.™
Processes of hydrogen peroxide decomposition catalyzed by PMn and PcMn are also important. Along with the widespread heme catalase, which is known to decompose hydrogen peroxide in living cells, non-heme catalase containing manganese ions have been found in a number of bacteria.[5,6] Mn111 porphyrins and phthalocyanines have also been utilized as building blocks for molecular magnets.[7,8]
Manganese tetraazaporphyrins and phthalocyanines are reported in a number of publications, where their
R R
R R
X-ray data,[910] EPR spectra,[1M4] electrochemical[1516] and catalytic[3,17"19] properties are described. The progress in the study and use of the properties of manganese complexes is substantially defined by their solubility in various solvents. We report here synthesis and spectral properties of a series of new manganese(III) complexes with substituted phenyl and phenoxy groups in macrocycle soluble in organic solvents.
Octaaryltetraazaporphyrins (Ar)8TAPMn(OAc), where Ar = m-trifluoromethylphenyl (m-CF3Ph) (1a) and p-tert-butylphenyl (p-fBuPh) (2a), and new manganese(III) octaaryl- and octaaryloxyphthalocyanines (Ar)8PcMn(OAc), where Ar = m-trifluoromethylphenyl (m-CF3Ph) (3a), m-trifluoromethylphenoxy (m-CF3PhO) (4a) and 3,5-di-tert-butylphenoxy (3,5-di-tBuPhO) (5a) were studied.
Experimental
Bis(p-tert-butylphenyl)fumaronitrile and 4,5-bis(3,5-di-tert-butylphenoxy)-phthalonitrile were prepared according to literature.[20-22] Octakis(m-trifluoromethylphenyl)tetraazapor-phyrin (m-CF3Ph)8TAPH2 (1), octakis(m-trifluoromethylphenyl)
R R R
R R
R R
la: R = m-CF3Ph 2a: R = p- BuPh
3: R = m-CF3Ph 4: R = m-CF.PhO
3a: R = m-CF3Ph 4a: R = m-CF3PhO
5a: R = 3,5-di-tBuPhO
1: R = m-CF3Ph 2:R = »-'BuPh
phthalocyanine (m-CF3Ph)8PcH2 (3) and octakis(m-trifluorometh-ylphenoxy)phthalocyanine (m-CF3PhO)8PcH2 (4) were synthesized as we have described earlier.123- 24]
Solvents for the synthesis, chromatography, and spectroscopic characterization of compounds were pure chemicals (Aldrich, Fluka).
The following equipment was used for characterization: Shimadzu UV-365 (UV-vis spectra); Bruker Tensor 27 (FT-IR spectra); Euro EA 3000 (elemental analysis); Bruker Autoflex MS (MALDI-TOF).
(Octakis(m-trifluoromethylphenyl)tetraazaporphyri-nato)manganese(III) acetate (m-CFph)8TAPMn(OAc), 1a. Mn(OAc)2-4H2O (53.2 mg, 0.21 mmol) and (m-CF3Ph)8TAPH2 (1) (51.4 mg, 0.035 mmol) were reacted in DMF (10 ml) at room temperature for 5 min with following addition of AcOH (3 drops). After 1 h the reaction mixture was poured into water and the formed precipitate was centrifugated, dried, dissolved in CH2Cl2 and chromatographed (silica gel/CH2Cl2). Yield: 26.0 mg (0.017 mmol, 47%), yellow-green powder. UV-vis (CH2Cl2) Xmax nm (lge): 406 (4.57), 461 (4.32), 654 (4.71). IR (KBr) vmax cm-1:1719 w, 1620 w, 1481 w, 1420 w, 1384 w, 1330 vs, 1312 s, '1279 w, 1169 s, 1128 s, 1098 m, 1076 s, 1016 m, 920 m, 810 m, 762 m, 722 m, 699 s. Found: C 54.33, H 2.40, N 6.95 %. C74H35N8F24O2Mn requires C 56.29, H 2.23, N 7.10 %. MS (MALDI-TOF) m/z: 1519.95 [(m-CF3Ph)8TAPMn]+ (calcd. for C72H32N8F24Mn 1519.0).
(Octakis(p-tert-butylphenyl)tetraazaporphyrinato) manganese(III) acetate (p-tBuPh)8TAPMn(OAc), 2a. A mixture of bis(p-tert-butylphenyl)fumaronitrile (1 g, 2.91 mmol) and Mn(OAc)2-4H2O (0.85 g, 3.48 mmol) in 2-dimethylaminoetha-nol (7 ml) was heated gradually with stirring to 150oC and the temperature was maintained for 10 h. Completion of the reaction was monitored by TLC, until no traces of starting material were detected. The reaction mixture was cooled, poured into 50 ml of methanol and the precipitate was centrifugated. For purification, the product was dissolved in chloroform and an equal amount of methanol was added to the solution. Chloroform was partially removed from the obtained solution using a rotary evaporator, and the formed precipitate was filtered off, chromatographed (silica gel/CHCl3-1%CH3OH) and dried under vacuum (60oC, 24 h). Yield: 0.52 g (0.35 mmol, 48%). UV-vis (CH2Cl2) Xmax nm (lge): 413 (4.42), 493 (4.38), 674 (4.58). IR (KBr) vmax cm-1: 2962 s, 2905 m, 2868 m, 1717 w, 1609 m, 1477 m, 1463 m, 1384 m, 1364 m, 1299 w, 1269 m, 1197 w, 1147 w, 1109 m, 997 s, 891 s, 850 w, 839 m, 811 s, 751 s, 635 w, 599 w, 585 w, 563 m. Found: C 78.82, H 7.47, N 7.31 %. C98H107N8O2Mn requires C 79.32, H 7.27, N 7.55 %. MS (MALDI-TOF) m/z: 1423.78 [(p-'BuPh)8TAPMn]+ (calcd. for C96H104N8Mn 1423.0). 8
(Octakis(m-trifluoromethylphenyl)phthalocyani-nato)manganese(III) acetate (m-CF3Ph)8PcMn(OAc), 3a. Mn(OAc)2-4H2O (41.0 mg, 0.17 mmol) and (m-CF3Ph)8PcH2 (3) (44.0 mg, 0.026 mmol) were reacted in DMF (10 ml) at room temperature for 1 h. The reaction mixture was treated further as described for 2a. Yield: 25.2 mg (0.014 mmol, 54%), deep-green powder. UV-vis (CH2Cl2) Xmax nm (lge): 392 (4.52), 525 (4.11), 739 (4.82). IR (KBr) vmax cm-1: 1721 w, 1624 m, 1508 w, 1422 w, 1385 w, 1333 s, 1256 w,m1217 w, 1169 s, 1128 s, 1101 s, 1077 m, 1042 w, 963 w, 899 w, 825 w, 805 m, 767 w, 749 w, 714 m, 658 s. Found: C 58.66, H 2.42, N 5.86 %. C90H45N8F24O2Mn requires C 60.69, H 2.55, N 6.29. MS (MALDI-TOF) m/z: 1721.25 [(m-CF3Ph)8PcMn]+ (calcd. for C^^Mn 1721.0).
(Octakis(m-trifluoromethylphenoxy)phthalocyani-nato)manganese(III) acetate (m-CF3PhO)8PcMn(OAc), 4a. Mn(OAc)2-4H2O (60.3 mg, 0.25 mmol) and (m-CF3PhO)8PcH2 (4) (61.9 mg, 0.034 mmol) were heated (100oC) in DMF (10 ml) and stirred for 48 h. The reaction mixture was cooled to room temperature and treated further as described for 2a. Yield: 38.2 mg (0.02 mmol, 58%), green powder. UV-vis (CH2Cl2) Xmax nm (lge):
389 (4.52), 515 (4.08), 724 (4.84). IR (KBr) vmax cm-1: 1720 w, 1617 m, 1594 m, 1492 m, 1450 s, 1409 m, 1385, "328 vs, 1283 s, 1208 w, 1174 s, 1128 s, 1086 m, 1065 m, 1039 w, 922 m, 794 w, 748 w, 697 m. Found: C 54.63, H 2.64, N 5.90 %. C90H45N8F24O10Mn requires C 56.62, H 2.38, N 5.87. MS (MALDI-TOF) m/z: 1849.21 [(m-CF3PhO)8PcMn]+ (calcd. for C88H42N8F24O8Mn 1849.0).
(Octakis(3,5-di-tert-butylphenoxy)phthalocyaninato) manganese(III) acetate (3,5-di-tBuPhO)8PcMn(OAc), 5a, was obtained by the reaction of 4,5-bis(3,5-di-tert-butylphenoxy) phthalonitrile (1.25 g, 2.33 mmol) and Mn(AcO)2 4H2O (0.25 g, 1.02 mmol) in hexanol-1 (6 ml) under reflux in the presence of DBU (6 drops) at 160oC. The reaction mixture was poured into 60 ml of methanol, precipitated by dropwise addition of water, and filtered. The obtained precipitate was dissolved in chloroform and chromatographed (silica gel/CHCl3-1%CH3OH). Yield: 0.61 g (0.27 mmol, 46%). UV-vis (CH2Cl2) Xmax nm (lg e): 393 (4.52), 513 (4.16), 735 (4.82). IR (KBr) vmax cm-1: 2963 s, 2928 m, 2868 w, 1725 w, 1608 m, 1586 s, 1508 w, "1459 s, 1421 s, 1407 s, 1384 w, 1363 m, 1337 w, 1296 s, 1246 w, 1199 s, 1119 w, 1084 m, 1042 w, 1002 w, 961 s, 903 w, 864 w, 745 w, 707 m. Found: C 77.37, H 8.65, N 4.74 %. C146H179N8O10Mn requires C 77.56, H 7.98, N 4.95. MS (MALDI-TOF) m/z: 2199.52 [(3,5-di-'BuPhO)8PcMn]+ (calcd. for C144H176N8O8Mn 2199.0). 8
Results and Discussion
Synthesis
The UV-vis spectra of (m-CF3Ph)8TAPH2 (1) in DMF exhibit two typical bands in the visible region with the absorption maxima at 594 and 655 nm (Figure 1). When Mn(OAc)2 is added to the solution of 1 in DMF at room temperature, the spectrum of metal-free 1 changes, resulting in two bands with absorption maxima at 561 and 644 nm and lower intensity (Figure 1). It remains unchanged for a some time. After addition of AcOH to the reaction mixture, the two-band spectrum immediately changes to a one-band spectrum with the maximum at 646 nm (Figure 1). After isolation of the resulting product in a solid state, it was dissolved in CH2Cl2 and its UV-vis spectrum was found to be similar to that2 of2 Ph8TAPMnIII(Cl) described earlier[25] (Table 1). The isolated TAPMn(OAc) (1a) gives a one-band spectrum in the visible region in pyridine or DMF respectively, as well as in the case of the other solvents (chloroform, dichlo-romethane). No second band at ~ 560 nm was observed. The
Figure 1. UV-vis (298 K) spectra of (ra-CF3Ph)8TAPH2 (1) in DMF (solid line), after the successive addition of Mn(OAc)2 (dotted line) and AcOH (dashed line).
same spectral changes with two bands at final spectrum were also observed in the reaction of octaphenyltetraazaporphy-rin Ph8TAPH2 and octa(p-bromophenyl)tetraazaporphyrin (p-BrPh)8TAPH2 respectively with Mn(OAc)2 in pyridine at room temperature,[25] as in the case when reaction of 1 with Mn(OAc)2 is proceeding in pyridine.
Table 1. UV-vis spectra of substituted PcMn and TAPMn.
Complex Solvent X nm (lgg) max, v ° '
1a CH2Cl2 406 (4.57), 461 (4.32), 654 (4.71)
2a CH2Cl2 413 (4.42), 493 (4.38), 674 (4.58)
Ph8TAPMn(Cl)[25] CHCl3 413 (4.40), 475(4.12), 665 (4.43)
3a CH2Cl2 392 (4.52), 525 (4.11), 739 (4.82)
4a CH2Cl2 389 (4.52), 515 (4.08), 724 (4.84)
5a CH2Cl2 393 (4.52), 513 (4.16), 735 (4.82)
tBu4PcMn(Cl)[16] benzene 351 (4.72), 518( 4.23), 725 (5.06)
tBu4PcMn[16] benzene 350, 680
tBu4PcMn[16] pyridine 350, 480,560, 660, 840, 880
Complexation of porphyrins[26] and azaporphyrins[27] with MnII salts in solution is commonly accompanied by an instantaneous oxidation of MnII to MnIII in the presence of air. Thus the compounds PMnm(X), having characteristic electronic absorption spectra, are formed. The spectra of tetraazaporphyrinatomanganese(III) contain one intense 0-band at 650-680 nm and an additional but weaker absorption band at 450-480 nm.[27]
The reaction of TAPH2 with Mn(OAc)2 in pyridine yields a product, the electronic absorption spectrum of which in the visible region contains two bands shifted hypsochromically as compared to that of TAPH2.[2328]
As it was shown by UV-vis spectroscopy for phthalo-cyanines, the axial coordination of Py causes the formation of manganese(II) complexes PcMn"-Py and PcMn"-2Py. [29] According to paper[16] there is intramolecular electron transfer resulting in the formation of two new forms of Mn11 complex - the radical-cation Pc+^Mn^wPy and radical-anion Pc-^Mnm-«Py, which are confirmed by UV-vis spectra (Xmax 560, 880 and 480, 840 nm, correspondingly). The possibility of formation of the ^-oxo complex (MnPcPy)2O was shown in paper[30]. However, it takes place when PcMn is dissolved in pyridine solution, but not in the process of the macrocycle complexation with Mn11 salt. We did not observe any spectrum similar to that of ^-oxo complex in our work.
The analysis of the experimental and literature data (Table 1) makes it possible to conclude that reaction of 1 with Mn(OAc)2 in DMF or pyridine yields Mn11 complex (Xmax = 644 nm) and the corresponding radical-cation (Xmax = 56l, 774 nm). Finally the product of complexation reaction after addition of AcOH is manganese(III) complex characterized by UV-vis, IR, and MALDI-TOF methods.
The formation of octakis(m-trifluoromethylphenyl) phthalocyaninatomanganese(III) acetate (3a) and octakis(m-trifluoromethylphenoxy)phthalocyaninatomanganese(III) acetate (4a) can also be achieved by direct metallation of the corresponding macrocycles. The spectral changes during the reaction of (m-CF3Ph)8PcH2 (3) with Mn(OAc)2 in DMF are displayed as an example in Figure 2. The UV-vis spectra of 3 in DMF and pyridine exhibit two typical bands with
absorption maxima at 682 and 713 nm. The reaction mixture spectrum however has a single absorption band at 693 nm. The intensity of this band decreases with time and finally it disappears completely (Figure 2), while a new absorption band appears at 724 nm. The spectrum of the resulting solution is similar to that of tBu4PcMn(Cl),[16] that specifies the formation of PcMn(OAc) (3a). The spectrum with Xmax = 693 nm corresponds probably to PcMn". Proceeding of the analogous comlexation reaction in unaerobic conditions leads to the formation of one product PcMnII [16] (Table 1), and the oxidation of Mn" to Mn'" under the air takes place during the purification. TLC of the reaction mixture 3 - Mn(OAc)2 in DMF at the beginning and at the middle of the reaction shows the presence of two compounds. DMF or pyridine can stabilize the +2 oxidation state of a central manganese atom at the moment of complex formation, but it cannot prevent the oxidation to manganese(III) phthalo-cyanine by air.
Figure 2. Changes of UV-vis spectra during the reaction of (ra-CF3Ph)8PcH2 with Mn(OAc)2 in DMF at 298 K, C(PcH2) = 1.910"5 moll-1, C(Mn(OAc)2) = 4.410"4 moll4 The time between the measurements is 5 min.
(p-tBuPh)8TAPMnm(OAc) (2a) and (3,5-di-tBuPhO)8PcMnIn(OAc) (5a) were prepared by cyclote-tramerization of the corresponding bis(p-tert-butylphenyl) fumaronitrile and 4,5-bis(3,5-di-tert-butylphenoxy) phthalonitrile in 2-dimethylaminoethanol or hexanol-1, respectively. Direct metallation of octakis(p-tert-butylphenyl) tetraazaporphyrin (2) by manganese(II) acetate did not result in the formation of 2a, because TAPH2 2 is not soluble even in boiling DMF, and its heterogeneous reaction with Mn(OAc)2 in refluxing DMF led only to the decomposition of macrocycle.
Characterization of the Compounds Prepared
Investigation of the physicochemical properties of 1a-5a confirms their molecular composition and gives an insight on the influence of the substituents on properties of the correspond compounds.
For all the compounds 100% peak of [PcMn]+ (or [TAPMn]+) in mass spectra was detected and no other fragmentation signals were observed (Figure 3). The absence of [PcMn(OAc)]+ (or [TAPMn(OAc)]+) peak indicates the dis-
sociation of the axial ligand under the conditions of MALDI experiment in the case of compounds with both electrofilic (CF3Ph, CF3PhO) and nucleophilic (BuPh, tBuPhO) groups suggesting electron buffer properties of tetraazamacrocycle in 1a-5a. This result is in agreement with IR (see lower) and UV-vis data.
The lgs values of the Q-bands of 1a-5a are in the range of 4.7-4.8 and are slightly dependent on the nature of the peripheral substituents in the case of TAP complexes and independent in Pc complexes. However, lgs values of 1a and 2a are lower than those found for axially coordinated indium complexes with octakis(m-trifluoromethylphenyl) tetraazaporphyrin and octakis(p-butylphenyl)tetraazapor-phyrin (with opposite electron effect of substituents).[24] The specificity of functional groups and coordination center in MnIII complexes explains this regularity. Obviously, electron -I effect of m-CF3Ph-, m-CF3PhO- groups gradually disappears along the chain of atoms and the positive effect of the conjugation of p-BuPh-, 3,5-di-tBuPhO- groups is not observed because the dative n-bonds Mn(3J4)^N taking place in manganese(III) porphyrin complexes[31] are absent due to strong n-acceptor properties of tetraazamacrocycle.
Two intense bands at 650-680 nm (Q-band) and 405415 nm (B--band) in the spectra of complexes 1a and 2a correspond to tc^tc* transitions. Comparison of the UV-vis spectra of PcMn(OAc) 3a-5a and the corresponding complexes of tetraazaporphyrins 1a and 2a (Table 1) shows that extension of the conjugated n-system of the macrocycle leads to the bathochromic shift of the Q-band (720-740 nm) and to the hypsochromic shift of the B-band (385-395 nm). This is in good agreement with the theoretical results:[32] annelation of benzene rings to the porphyrazine macrocycle results in the n-MOs destabilization, which increases in the order a, < e * < a. . Similar bathochromic shift of the Q-band was
lu g 2u
observed in the order of m-CF3Ph- > m-CF3PhO- > p-BuPh-> 3,5-di-tBuPhO- substituted complexes of Mnm. Thus the
electronic effect of substituents on the coordination center is not observed, but the p-tert-butylphenyl groups conjugation with aromatic macrocycle takes place.
The most intense bands in the IR spectra of 1a-5a are in the region of 500 - 1700 cm-1 and are caused by combined vibrations of peripheral phenyl rings and the macrocycle skeleton. They are similar to those observed for the same complexes with magnesium and indium,[24,33] and their frequencies are practically independent on the nature of the metal. The FT IR spectra of 2a and 5a show additional intense bands at 2963 , 2905-2928, 2868 cm-1 due to the stretching vibrations of the tert-butyl groups. Very intense stretching vibrations of CF3- groups in peripheral aromatic rings, along with the mixed vC_F and deformational aryl ring modes, are dominating in the spectra of 1a, 3a and 4a. They
were observed at approximately 1330, 1170, 1127 and 1071 cm-1.
The presence of the axial ligand AcO- was verified by IR spectroscopy. The characteristic vibrations of axial AcO- group were observed at approximately 1620 and 1384 cm-1, and their frequencies are practically independent of the nature of the macrocycle.
EA data for the prepared compounds are, generally, in satisfactory agreement with the calculated values. However, the relatively low conformity of the found and theoretical values for carbon in case of fluorinated TAPMn 1a and PcMns 3a and 4a can result from the influence of the high content of fluorine. Similar difficulties in combustion analysis were also observed in case of fluorine-containing phthalo- and naphthalocyanines,[34-36] but not in works [37,38].
The preliminary investigation of light stability of some of the prepared compounds was carried out in chloroform or dichlormethane solutions in a quartz cuvette, directly exposed to daylight for several days. Under this conditions, no decomposition was observed for compounds 1a-5a. Because of their observed comparatively high stability in
Figure 3. MALDI-TOF spectra of compounds 1a and 3a.
solutions in the presence of air, such complexes could be used as catalysts for various oxidation processes.
Among the synthesized complexes compound 5a is the most perspective for research of liquid crystal properties as the calculation of molecular parameters and the preliminary mesomorphism forecast has shown 50% probability of thermotropic mesophase presence at this substance. Calculation and the forecast were conducted by Dr. Akopova O.B. using molecular mechanics method (MM+ force field) (HyperChem Pro 6.0) and original software product CMP ChemCard for all complexes.[39]
Acknowledgements. We thank Deutsche Akademische Austauschdienst (DAAD) and the Ministry of Education and Science of Russian Federation for financial support of this work within the Russian-German program "Mikhail Lo-monosov" and Dr. Akopova O.B., Ivanovo State University, Russia.
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Received 27.10.2009 Accepted 15.03.2010 First published on the web 19.03.2010
