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Matsushita O.,Tohoku University | Derkacheva V.M.,Organic Intermediates and Dyes Institute | Muranaka A.,RIKEN | Muranaka A.,Japan Science and Technology Agency | And 5 more authors.
Journal of the American Chemical Society | Year: 2012

Expanded phthalocyanine (Pc) congeners with two Mo or W central metal ions and four isoindole ring moieties have been synthesized using normal Pc formation conditions in the presence of urea. The products have been characterized by electrochemistry; mass spectrometry (MS); IR, electron paramagnetic resonance (EPR), NMR, electronic absorption, and magnetic circular dichroism (MCD) spectroscopies; and X-ray analysis. The X-ray structures have rectangular C 2v symmetry and provide evidence that the central Mo atoms are linked by a single bond and coordinated by two isoindole nitrogen atoms and two nitrogen atoms from the amine moieties. The electronic absorption bands extend into the 1200-1500 nm region. This can be explained using Gouterman's four-orbital theory. The experimental NMR data and theoretical calculations provide evidence for a heteroaromatic 22-π-electron conjugation system for the ring-expanded Pc system, which satisfies Hückel's (4n + 2)π aromaticity. © 2012 American Chemical Society.


Nemykin V.N.,University of Minnesota | Polshyna A.E.,University of Minnesota | Makarova E.A.,University of Minnesota | Makarova E.A.,Organic Intermediates and Dyes Institute | And 2 more authors.
Chemical Communications | Year: 2012

Minor products in the reaction between substituted 1,3-diiminoisoindolines and 2,5-diamino-3,4-dicyanothiophene were identified as the nickel seco-tribenzoporphyrazines 4 and 5, which have been characterized by UV-vis, MCD, NMR, and mass spectroscopy. Experimentally observed tetraazachlorin-type UV-vis spectra of new seco-tribenzoporphyrazines were explained on the basis of DFT and TDDFT calculations. © 2012 The Royal Society of Chemistry.


Lukyanets E.A.,Organic Intermediates and Dyes Institute | Nemykin V.N.,University of Minnesota
Journal of Porphyrins and Phthalocyanines | Year: 2010

The preparation and optical properties of peripherally substituted phthalocyanines and their analogs (i.e. naphthalocyanines, anthracyanines, aza-analogs of phthalocyanines, and tetraazaporphyrins) have been widely discussed. This review highlights methodologies that have been published in poorly known and mostly unavailable Russian journals. © 2010 World Scientific Publishing Company.


Solntsev P.V.,University of Minnesota | Dudkin S.V.,University of Minnesota | Dudkin S.V.,Organic Intermediates and Dyes Institute | Sabin J.R.,University of Minnesota | Nemykin V.N.,University of Minnesota
Organometallics | Year: 2011

Orange dimethyl (Z)-2,3-bis(ferrocenyl)-2-butenedioate (1) and blue (Z)-2,3-bis(ferrocenyl)maleimide (2) were prepared and characterized using NMR, IR, and UV-vis spectroscopy as well as X-ray crystallography. X-ray crystallographic studies of 1 and 2 revealed a locked anti conformation of the ferrocene substituents, which was explained on the basis of the steric properties of these groups. Electronic structures and solvatochromic properties of 1 and 2 were investigated by UV-vis spectroscopy and polarized continuum model (PCM) density functional theory (DFTPCM) as well as time-dependent DFT (TDDFT-PCM) approaches. The calculated vertical excitation energies are consistent with the experimental data and clearly suggest the dominance of metal-to-ligand charge-transfer bands in the visible region of the UV-vis spectra for 1 and 2. Redox properties of 1 and 2 were investigated using cyclic voltammetry, differential pulse voltammetry, and spectroelectrochemical and chemical oxidation approaches. In aDCM/(NBu4)[B(C6F 5)4] system, ferrocene-centered oxidation processes in 1 and 2 are separated by 300 and 345 mV, respectively. Stepwise chemical and spectroelectrochemical oxidation of 1 and 2 allowed us to obtain spectroscopic signatures of the mixed-valence 1+ and 2+ cations. Hush analysis of the intervalence charge-transfer bands in 1+ and 2 + is suggestive of class II (in Robin and Day classification) behavior. © 2011 American Chemical Society.


Nemykina V.N.,University of Minnesota | Lukyanets E.A.,Organic Intermediates and Dyes Institute
Arkivoc | Year: 2010

This review summarizes the synthetic strategies for substituted phthalonitriles and phthalocyanines. Preparation of alkyl-, aryl-, halo-, nitro-, alkoxy-, aryloxy-, alkylthio-, arylthio-, and amino- substituted phthalocyanines along with the derivatives of phthalocyanine carboxylicand sulfoacids is overviewed. Influence of the substituents on the position of Q-band in UV-vis spectra of substituted phthalocyanines is also briefly discussed.


Makarova E.A.,Organic Intermediates and Dyes Institute | Dudkin S.V.,Organic Intermediates and Dyes Institute | Lukyanets E.A.,Organic Intermediates and Dyes Institute
Journal of Porphyrins and Phthalocyanines | Year: 2013

An efficient synthetic route for the preparation of benzene or 1,2-naphthalene fused and phenyl substituted metal-free tetraazachlorins with yields up to 40% was developed using In(III) as a removable template. New substituted tribenzotetraazachlorins derivatives with tert-butyl and phenylsulfanyl groups in β and α position of fused benzene rings, correspondingly, were synthesized by novel approach and their spectral properties were investigated. © 2013 World Scientific Publishing Company.


Negrimovsky V.,Organic Intermediates and Dyes Institute | Volkov K.,Organic Intermediates and Dyes Institute
Journal of Porphyrins and Phthalocyanines | Year: 2013

Hexadecasubstituted CoPc and ZnPc containing different number of N-methylpyridiniumoxy groups and chlorine atoms were synthesized. It was shown that increasing number of cationic groups leads both to increased solubility of complexes in dipolar aprotic organic solvents and in water, and to increased contribution of monomeric form in aggregation equilibrium in water up full disaggregation. © 2013 World Scientific Publishing Company.


Kuznetsova N.A.,Organic Intermediates and Dyes Institute | Kaliya O.L.,Organic Intermediates and Dyes Institute
Macroheterocycles | Year: 2015

Heterogeneous systems synthesized by grafting of phthalocyanines to aminopropyl silica gel can exhibit high photobactericidal and photovirucidal activity. In this review, recent works of Russian group in the field are summarized. Ways to achieve low aggregation degree and high ability in singlet oxygen generation for immobilized phthalocyanine as well as effects of charge of attached phthalocyanine, support pore size, length of spacer between dye and silica upon efficacy of heterogeneous sensitizers in photodynamic microorganism inactivation are considered. © ISUCT Publishing.


Dolotova O.,Organic Intermediates and Dyes Institute | Kaliya O.L.,Organic Intermediates and Dyes Institute
Journal of Porphyrins and Phthalocyanines | Year: 2011

Ethylenediamine-N,N′-diacetic acid complexes of the covalent conjugates of octacarboxy-substituted cobalt phthalocyanine with one, two and three platinum atoms (3ac) were synthesized and characterized by elemental analysis, electronic absorption, infrared and mass spectra data. © 2011 World Scientific Publishing Company.


Kuznetsova N.A.,Organic Intermediates and Dyes Institute | Kaliya O.L.,Organic Intermediates and Dyes Institute
Journal of Porphyrins and Phthalocyanines | Year: 2012

Metallophthalocyanines form a very important class of commercial dyes and have achieved significant success in a variety of applications, in which their photostability is of fundamental importance. On this ground, considerable data on phthalocyanine photobleaching were published over recent years. We do not intend to give exhaustive compilation of the photobleaching quantum yields, which are known for wide circle of phthalocyanines in different solvents. This review begins by discussing pertinent background information about processes following phthalocyanine excitation. Then using selected examples of the recent literature, including authors' works, we survey a variety of photobleaching effects from the fundamental origins to specific for phthalocyanine chromophore. Finally, the mechanisms of phthalocyanine oxidative photobleaching are discussed. Copyright © 2012 World Scientific Publishing Company.

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