Reactivity of tetra-4(4-methoxyphenoxy)-phthalocyanine in acid-base interaction with nitrogen-containing organic bases

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Abstract

Interaction of tetra-4(4-methoxyphenoxy)phthalocyanine with pyridine, 2-methylpyridine, morpholine, piperidine, n-butylamine, tert-butylamine, diethylamine, and triethylamine in benzene and the benzene-dimethylsulfoxide system is studied. The acid-base interaction reaction belongs to the number of unusually slow processes and leads to the formation of time-stable complexes with proton transfer. Their structure is proposed. The change of reactivity of tetra-4(4-methoxyphenoxy)phthalocyanine depending on the polarity of the medium, proton acceptor ability, and spatial structure of the nitrogen-containing base is considered.

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О. A. Petrov

Ivanovo State University of Chemistry and Technology

Author for correspondence.
Email: poa@isuct.ru
Russian Federation, Ivanovo

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Supplementary files

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2. Scheme

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3. Fig. 1. Electronic absorption spectrum of H2Pc(R)4 in benzene (1) and n-butylamine (2) at 298 K.

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4. Fig. 2. Change in the electronic absorption spectrum of H2Pc(R)4 in the presence of n-butylamine for 75 min at 323 K and CoBuNH2 = 5.06 mol/l in benzene.

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5. Fig. 3. Dependences of ln(Co/C) on the reaction time of H2Pc(R)4 with BuNH2 (1) and Pip (2) in benzene at T = 323 K (1, 2) and CoBuNH2 = CoPip = 5.06 mol/l.

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6. Fig. 4. Dependences of lgkH on lgCoB for the reaction of H2Pc(R)4 with BuNH2 (1) and Pip (2) in benzene at T = 323 (1) and 333 K (2).

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7. Fig. 5. Geometric structure of the H2Pc(R)4 complex with n-butylamine (a), diethylamine (b) and morpholine (c), optimized by the B3LYP method and the 6-31*G(d, p) basis set.

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