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13Порфирины
Porphyrins
Макрогэтэроцмклы
Microreview
Миниобзор
http://macroheterocycles.isuct.ru
DOI: 10.6060/mhc140611g
Survey of Synthetic Routes towards Phosphorus Substituted Porphyrins
Alla G. Bessmertnykh-Lemeune,a Christine Stern,a Yulia G. Gorbunova,bc Asian Yu. Tsivadze,bc and Roger Guilarda@
Dedicated to the Corresponding member of Russian Academy of Sciences Prof. Oscar Koifman
on the occasion of his Anniversary
aInstitut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB), 21078 Dijon, France
hA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russia cN.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences,119991 Moscow, Russia @Corresponding author E-mail: Roger.Guilard@u-bourgogne.fr
This brief review summarizes the synthetic approaches towards porphyrins bearing a C-P bond at the periphery of the macrocycle. In the first section we detail the non catalytic pathways for the synthesis of phosphorus substituted porphyrins using different phosphonate precursors or by derivatization of a pre-existing porphyrin. In the second section we demonstrate that palladium- or copper-catalyzed phosphorylation of halogen substituted porphyrins is an efficient method to prepare meso- and fi-phosphoryl substituted porphyrins.
Keywords: Phosphoryl porphyrins, transition metal catalized cross-coupling, formation of C-P bonds, pyrrole,
Синтетические подходы к получению фосфор-замещенных порфиринов
А. Г. Бессмертных-Лемен,а К. Штерн,а Ю. Г. Горбунова,b,c А. Ю. Цивадзе,Ьс P. Гиляра@
Посвящается Член-корреспонденту РАН, профессору О. И. Койфману по случаю его юбилея
Институт молекулярной химии Университета Бургундии, 21078 Дижон, Франция ЪФГБУНИнститут физической химии и электрохимии им. А.Н. Фрумкина РАН, 119071 Москва, Россия °ФГБУНИнститут общей и неорганической химии им. Н.С. Курнакова РАН, 119991 Москва, Россия @E-mail: Roger. Guilard@u-bourgogne.fr
B кратком обзоре обсуждаются методы синтеза порфиринов, содержащих связь C-P на периферии макро-цикла. Первая часть обзора содержит сведения о некаталитических подходах к получению фосфор-заме-щенных порфиринов с использованием различных фосфонатных прекурсоров, в том числе исходя из предварительно синтезированных замещенных порфиринов. Вторая часть обзора посвящена обсуждению эффективных синтетических подходов к получению мезо- и fi-фосфорилпорфиринов из галоген-замещенных производных порфиринов и диалкилфосфитов в присутствии комплексов переходных металлов.
Ключевые слова: Фосфорилпорфирины, катализируемые переходными металлами реакции кросс-сочетания, образование связи C-P, пиррол, фосфор.
phosphorus.
Introduction
Many papers and reviews have been dedicated to the synthesis and substitution of the porphyrin core to obtain macrocyclic derivatives for a specific property and a particular application,11-51 but only few papers are related to studies of phosphoryl porphyrins. However, the presence of a phos-phonate group at the periphery of the macrocycle is essential to graft a dye on a semiconductor and more generally such type of receptors can be used as assembling ligand. Some studies investigated the effects of the anchoring group nature to improve the light collection efficiency of DSSCs or others and mainly to compare the efficiency of carboxylate versus phosphonate moieties as grafting groups.[6-10] More generally phosphoryl porphyrins can be used to fabricate photonic materials, for studies of biological systems or to elaborate molecular solids displaying sensor and catalytic properties.
Only a few syntheses of porphyrins bearing a C-P bond at the periphery of the macrocycle were described due to the limited availability of an appropriate synthetic method. In this review we only detail the synthesis of derivatives possessing a pentavalent phosphorus component. Two synthetic approaches can be employed to prepare phosphoryl porphyrins - non catalytic pathway or transition metalmediated cross-coupling reactions.
Non Catalytic Pathways for C-P Bond Formation at Porphyrin Periphery
Reactions Using Susbtitution of Porphyrinic Macrocycles
In a pioneering work Smith and coworkers described in 1977 the introduction of a weso-triphenylphosphonium substituent at the porphyrin periphery via a radical cation formation.[1112] Treatment of Zn(II)-octaethylporphyrin with tris(p-bromophenyl)ammoniumylhexachloroantimonate generates the n cation radical of the porphyrin which was reacted with triphenylphosphine. A demetallation reaction gave the weso-triphenylphosphonium octaethylporphyrin chloride 1, but the UV-visible absorption spectroscopy indicated that there was a significant resonance contribution from the porphyrin cation. The relative stability of the phosphonium salt limited the extension of the Wittig reaction into porphyrin chemistry. This was attributed to the highly stabilized ylide 2 and the steric repulsion of the reactants.
The structure of 2 possesses a variant of the theoretically interesting isoporphyrin chromophore (Scheme 1).
PPh3 Et
Scheme 1.
(P-Porphyrinyl)phosphonium salt 3 generated from Zn(II)-tetraphenylporphyrin was first reported by Shine et al. (Scheme 2).[13-14]
The same phosphonium salt 3 was synthesized by Giraudeau et al. from the corresponding electrochemically generated cation radical.[15] In parallel the analogous P-phosphonium salt was obtained from a chemically generated Fe(III)-tetraphenylporphyrin cation radical after treatment with PPh^16
Through the electrochemical procedure, Giraudeau et al. have prepared di- and triporphyrins linked by phosphonium bridges.[17-19] The electrochemically generated Zn(II)-tetraphenylporphyrin cation radical was treated with di- and triphosphines to yield porphyrin oligomers, as an example the dimer 4 (Scheme 3).[17]
The free base tris(mesityl) porphyrin 6a has been also obtained by treating the bromoporphyrin 5 with trimethyl phosphite according Arbuzov reaction in 79 % yield (Scheme 4).[20]
One complementary route allowed the preparation of di-tert-butyl porphyrinic phenylphosphonates by acting di-tert-butyl phosphite with an iodo-phenyl substituted porphyrin with di-tert-butyl phosphite in a Pd-mediated coupling process.[21]
In 2004 Uemura and coworkers prepared the porphyrinthioyl hybrid ligand by treatment of 3'-(di-phenylphosphinothioyl)biphenyl-2-carbaldehyde 7 with dipyrromethane in the presence of trifluoroacetic acid followed by oxidation with p-chloranil (Scheme 5).[22] A mixture of syn- and anti-isomers was formed but only the syn-isomer 8 was isolated as a pure derivative in 21 % yield.
-e PPh3
CI04"
Scheme 2.
Ph
PPh2
0.5 eq PPh2
2,6-lutidine -►
- e 72%
Ph
Scheme 3.
=\ Br P(OMe)3
toluene 79%
O. .OMe OMe
Scheme 4.
syn-9
Scheme 5.
The corresponding syn-zinc porphyrin 9 was obtained by metallation with Zn(OAc)2 in 98 % isolated yield.
Two main synthetic approaches can be employed to prepare porphyrins bearing phosphonate units. Indeed, the phosphonate moiety can be introduced either into precursors of the porphyrin or by derivatization of a pre-existing porphyrin scaffold. The first described syntheses were mainly based on the first strategy while the second one has been successfully developed more recently. These two strategies are detailed below.
Synthesis of Porphyrins Using Phosphonate Precursors
The first preparation of manganese porphyrins tetrafunctionalized with phosphonic acid has been reported by Bujoli and coworkers in 1995.[23] This synthesis based on the classical condensation of pyrrole with the corresponding aldehyde under Adler conditions has been then described by Odobel and coworkers to form porphyrin (Scheme 6).[24]
The meso-tetraaiylporphyrins 10 have been prepared by condensation of pyrrole with the para- and meta-phosphoiyl substituted benzaldehydes, while the /rans-porphyrin A2B2 11 was obtained through the MacDonald [2+2] condensation of 5-phenyl-dipyrromethane with the functionalized benzaldehyde (Scheme 7).[24] It has to be noted that the functionalized benzaldehydes were prepared by Hirao's reaction. Protection of the aldehyde group is needed to obtain the target precursors under these conditions in good yields.
Over the same period Lindsey and coworkers synthesized phosphonic acids attached to porphyrins by
condensation reactions of pyrrole with the phosphonic ester derived reagent and mesitaldehyde (Scheme 8).[20]
The precursor phosphonate aldehyde 12 was obtained in three steps from a-bromo-p-toluic acid. Arbuzov reaction of this acid with diethylphosphite was used to introduce the phosphorus substituent.
The cocondensation of this aldehyde, mesitaldehyde and pyrrole at high concentration using BF3-O(Et)2/ethanol co-catalysis gave a mixture of porphyrins from which the A3B porphyrin 6b was obtained in 9.4 % yield. The zinc complex 13 obtained in 94 % yield was treated with TMS-Br and TEA in refluxing CHCl3 to induce cleavage of the ethyl protecting groups giving porphyrin benzylphosphonic acid 14 in 78 % yield.
Lindsey and coworkers also reported univocal synthesis of a porphyrin-phosphonic acid bearing p-tolyl groups at three meso-positions by condensation of a phosphonate substituted dipyrromethane 15 and a dipyrromethane-dicarbinol 16 (Scheme 9).[20] The condensation of 15 and 16 using InCl3 as catalyst led to a free base porphyrin which after metallation with Zn(OAc)2-2H2O afforded the Zn(II) complex 17.
Catalytic Pathways for Synthesis of Phosphoryl Porphyrins
In 2006 Arnold and coworkers described a new class of porphyrins with one and two diphenylphosphine oxide substituents in meso-position (Scheme 10).[2526]
Attempts to obtain meso-porphyrinyl phosphine by the method of Stille led to the corresponding phosphine oxide
CHO
N
I
H
P03Et2
C2H5COOH
A 30-33 %
Scheme 6.
CHO
P03Et2
C2H5COOH
A 31 %
Scheme 7.
P03Et2
Et203P
P03Et2
10
Et203P
P03Et2
\ /) OEt
12
1) mesitaldehyde, pyrrole, BF3OEt2/ethanol, CHCI3
2) DDQ
9.4 %
TMS-Br, TEA
CHCI3 78%
Zn(0Ac)2-2H20 CHCI3/MeOH
94%
13
OEt
Scheme 8.
+ Me
15
1) lnCI3 CH2CI2
2) DDQ'
Me -Me
3) Zn(0Ac)2-2H20 CHCI3/MeOH
OEt
Scheme 9.
Ph2PSiMe3
(CH3CN)2PdCI2 cat.
-»
2 % (X = Br) 20 % (X = I)
18a (X = Br); 18b (X = I) Ar: 3,5-bis(f-butyl)phenyl
Scheme 10.
19 because these phosphines tend to oxidize very readily in
the presence of porphyrins to the corresponding oxides. The
target product was obtained in very low yields of 2 % when the
bromoporphyrin 18a was the porphyrinic precursor. A higher yield of 20 % was obtained starting from iodoporphyrin 18b
which is more reactive.
In another experiments the palladium complex 20 which is the intermediate compound in the suggested palladium-catalyzed reaction was used as starting material.[26] This intermediate 20 is readily available from a stoichiometric oxidative addition of the corresponding bromoporphyrin to [Pd2dba3] in the presence of dppe ligand. The reaction of 20
with Ph2P(O)H and Cs2CO3 as a base gave the phosphine oxide 21 in excellent yield (85 %) (Scheme 11).[26]
Corresponding nickel and zinc porphyrins substituted in one or two weso-positions by diphenylphosphine oxide groups have been prepared also by the palladium-catalyzed reaction of diphenylphosphine or its oxide with the corresponding bromoporphyrins. Complexes were isolated in yields of 60-95 %.[26] Attempts to isolate tertiary phosphines using the reduction by Cl3SiH or LiAlH4 failed due to extreme air sensitivity of these phosphines.
Arnold and coworkers have also described the coordination properties of porphyrinyl phosphine oxide towards Mg(II) porphyrins.[27] As an example, the coordination of the Mg(II) diphenylporphyrin 22 with the
free base porphyrinylphosphine oxide 21 or its Ni complex 23 gave the corresponding diporphyrins 24 and 25 (Scheme 12). These complexes were isolated in excellent yield (> 92 %) and it was shown that Mg(II) porphyrins have a very high affinity towards phosphine oxides.
The same group has also prepared the first strong binding synthetic analogue 26 of the "special pair" of the photosynthetic reaction center by insertion of Mg(II) into the free base 21 (Scheme 13).[27]
In 2007 Matano and coworkers reported the synthesis of two kinds of weso-phosphorylporphyrins by copper-catalyzed C-P coupling of weso-iodoporphyrinatozinc 27 with di-«-butylphosphite under Buchwald's conditions (Scheme 14).[28] weso-(Di-w-butoxyphosphoryl) porphyrinatozinc 28
Ph2P(0)H, Cs2C03
85%
Scheme 11.
Ph +
22
Ph
21 : M = 2H 23 : M = Ni
24 : M = 2H
25 : M = Ni
Scheme 12.
MgBr2 75%
26
Scheme 13.
27
(Bu0)2P(0)H
I Cul, Cs2C03
MeNH(CH2)2NHMe
81 %
Ph2P(0)H
72%
P(0)Ph2
Scheme 14.
was obtained in 81 % yield using 20 mol% Cul, 1,2-dime-thylethylenediamine as a ligand and Cs2CO3 as a base. Using diphenylphosphine oxide instead of di-«-butylphosphite gave the corresponding meso-diphenylphosphorylporphyri-natozinc 29 in 72 % yield.
In the course to prepare porphyrin dimers linked by peripherally fused phosphametallocycles in palladium and platinum series, the same group used the Pd-catalyzed C-P cross-coupling reaction of meso-iodoporphyrins (27, 30) with diphenylphosphine in MeCN/THF to produce the corresponding meso-(phosphinyl)porphyrins (31a,b) (Scheme 15).[29] This air sensitive derivative was readily oxidized in air to meso-phosphoryl porphyrin (32a). Consequently, the crude reaction mixture of 31a,b was reacted with elemental sulfur to afford the air stable meso-(thiophosphoryl)porphyrin (33a,b) in 87-92 % yields. The quantitative desulfurization of
these derivatives were obtained by treatment with excess of P(NMe2)3 in refluxing toluene.
Palladium-catalyzed phosphorylations both at the meso position of the porphyrin ring and at the p-bromophenyl substituents were described by Enakieva et al.[30-32] The A4 and A2B2 porphyrin types were obtained, the A2B2 type being isolated in modest to good yields depending of the reaction conditions (Scheme 16).
First, these reactions performed with diethylphosphite, Pd(OAc)2/PPh3 and Et3N in ethanol show that the nature of the reaction solvent is a key parameter. Indeed, a good yield of the 5,15-bis-(diethoxyphosphoryl)-10,20-diphenyl-porphyrinatozinc 37 (51 %) was described by Kadish et al. when ethanol was used as a solvent and dibromide 34 as the precursor (Scheme 17).[31] Moreover, the phosphorylation reaction of the Zn porphyrin gave
27: Ar = 3,5-(f-Bu)2C6H3 30: Ar = 2,4,6-Me3C6H2
Ph2PH, Et3N Pd(OAc)2
СН3СМЯНР
(E = O) 32a < air_ 31a,b (E = lone pair)
A
S8 P(NMe2)3
33a,b (E = S)
(a : precursor 27) (b : precursor 30)
Scheme 15.
(Et0)2(0)P
(Et0)2(0)P
P(0)(0Et)2
(Et0)2(0)P
P(0)(OEt)2
(Et0)2(0)P
P(0)(0Et)2
P(0)(0Et)2
Scheme 16.
HP(0)(0Et)2 Pd(OAc)2, PPh3
NEt3, EtOH
(Et0)2(0)P
P(0)(0Et)2
P(0)(0Et)2
34 : M = Zn, R = H
35 : M = Zn, R = CH3
36 : M = 2H, R = H
37 : M = Zn, R = H
38 : M = Zn, R = CH3
39 : M = 2H, R = H
40 : M = Zn, R = H
41 : M = Zn, R = CH3
42 : M = 2H, R = H
Scheme 17.
P(0)(0Et)2
HP(0)(0Et)2
Pd(OAc)2 PPh3
Br-:-(Et0)2(0)P
NEt3 EtOH
P(0)(0Et)2
P(0)(OEt)2 44
Scheme 18.
HP(0)(0Et)2 Pd(OAc)2 PPh3
NEt3 EtOH
(EtO)2(Q)P
P(0)(0Et)2
Scheme 19.
HP(0)(0R)2, Cul, L Cs2C03
L=CH3NH(CH2)2NHCH3
Ph P(0)(0R)2
47
Scheme 20.
higher yield of the target product compared to the reaction involving the corresponding free base 36 as a precursor. A hydrodebromination reaction was also observed under these conditions giving the porphyrins without phosphoryl groups and the monophosphoryl derivatives (40-42).
It is remarkable to note that the above conditions have been used to prepare the meso-tetra-(4-diethoxyphosphoryl) phenylporphyrins where the diethoxyphosphoryl substituents are attached to the meso-position of the porphyrin macrocycle via an aiyl spacer. The four C-P bonds can be formed in a one-pot procedure from 43 to give a tetraphosphoryl substituted A type porphyrin 44 (Scheme 18).[30] The yield observed for
the preparation of this complex was much higher (68 %) than the yield observed for the phosphorylation of the free base in toluene.[33]
The A2B2 type phosphorylated porphyrin 46 was obtained using the same conditions by phosphorylation of the tetrabrominated 45 precursor where two bromine atoms are directly linked to the macrocycle ring and another two bromine atoms through an aryl spacer (Scheme 19).[31]
The first synthesis of zinc P-phosphorylporphyrins was reported by Vinogradova et al.[34] P-Dialkoxyphosphoryl tetraphenylporphyrins and their Zn complexes were synthesized using Cu and Pd catalysts.
\
Ph Br
\
Ph P(0)(OR)2
Ph
Ph-
-NH
-N
HN'
/
-Ph + HP(0)(0R)2
Pd/L
Ph 49
Ph
Ph
50a,b
R : a = Et, b = n-Bu
Ph
Scheme 21.
HP(0)(0Et)2
Pd(OAc)2/3PPh3 NEt3
52 - 53
Scheme 22.
The reaction of zinc bromoporphyrinate 47 with dialkyl phosphite was studied using the Buchwald's catalytic system (Scheme 20).[34] The target products 48 were only obtained in high yield (> 85 %) when the precursor was reacted with phosphites using an excess of copper iodide (3 equiv.) and diamine (21 equiv.). In fact the key parameter of the reaction is the presence of the diamine because the aimed product is not formed in the absence of this ligand.
The reactivity of the H2TPPBr 49 and ZnTPPBr 47 in the presence of palladium catalysts was different compared to the weso-dibromoporphyrins. The best yield have been obtained using [Pd(OAc)2/3PPh3] (1 equiv.) and NEt3 when toluene was used as a solvent instead of ethanol. This can be due to the low solubility of H2TPPBr in ethanol which was the best solvent for weso-dibromoporphyrins. The product 50a was isolated in 87 % yield, H2TPP being the only side product (Scheme 21).[34] Surprisingly the reactivity of H2TPPBr is similar to that of ZnTPPBr and full conversion of the starting bromide using the optimal conditions is obtained.
Catalytic conditions were also studied to perform the coupling of 49 with diethylphosphite. Changing the system
from [Pd(OAc)2/3PPh3] to Pd(PPh3)4 led to complex 50a in 72 % yield using 25 mol% of catalyst. Further decrease in the catalyst loading to 15 mol% led to an incomplete conversion of 49 and a significant increase of by-product (H2TPP).
These Pd-catalyzed reactions further applied to the 2,3,12,13-tetrabromo-5,10,15,20-tetraphenylporphyrin (H2TPPBr4) 51 gave the starting material and a complex mixture of products (Scheme 22).[34] The MALDI-TOF and NMR spectral analysis of the mixture led to assume that the phosphorylation reaction takes place only after the reduction of one of the neighbouring bromine to form a mono-p-diethoxyphosphoryl substituted pyrrole moiety. Finally, it was shown that a mixture of toluene and ethanol was needed to increase the solubility of the porphyrin, to facilitate the reduction and the consecutive phosphorylation of the resulting bromoporphyrins. By using a specific rate of solvents (ethanol/toluene 2:3), the two bis(phosphoryl) porphyrins 52 and 53 were obtained in equal amounts with a global yield of 81 %. The separation of regioisomers by column chromatography is difficult but the corresponding zinc complexes obtained by metallation of the free bases mixture were separated by chromatography.
Syntheses of Phosphorus Substituted Porphyrins Conclusions
This review focused on the synthesis of phosphoiyl substituted porphyrins demonstrate clearly that the transition metal-mediated or catalyzed C-P bond-forming reactions can be successfully applied to the synthesis of essential precursors possessing phosphonate moieties as anchoring groups. Indeed for a long time, most of the phosphonate porphyrins used as structural blocks in material chemistry, for mimicking biological processes or building blocks for self organization of highly ordered assemblies were porphyrins substituted by phospho-nate moieties not directly linked to the meso- or P-pyrrolic position of the macrocycle. The transition metal-catalyzed C-P cross coupling reaction of meso- or P-halogenoporphyrins led to new series of A4, A3B, A2B2 types porphyrins which exhibit a priori new and novel chemical and physical properties. It was already shown that the self assembling of these phosphoiyl Zn(II) and Cu(II) porphyrins should be observed in solid state and in solution.[30-32,34,35] This self assembling leads to 1D and 2D networks. At last but not least, the new A3B type phos-phorylated porphyrins should be very good precursors in order to construct efficient DSSCs and to develop photocatalysts. It is very well known that the efficiency of the electron transfer step at a dye semi-conductor is dependent on how the chromo-phore is attached to the surface.
Acknowledgements. This work was performed in the frame of the French-Russian Associated Laboratory "LAMREM" supported by the CNRS and the Russian Academy of Sciences, Russian Foundation for Basic Research (grant #12-03-93110).
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Received 02.06.2014 Accepted 10.06.2014
