Supramolecular assemblies based on crown- and phosphoryl-substituted phthalocyanines and their metal complexes in microh
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Supramolecular assemblies based on crown- and phosphoryl-substituted phthalocyanines and their metal complexes in microheterogeneous media* N. F. Goldshleger,a M. A. Lapshina,a V. E. Baulin,b A. A. Shiryaev,c Yu. G. Gorbunova,c,d and A. Yu. Tsivadzec,d aInstitute
of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation. E-mail: [email protected] bInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyj proezd, 142432 Chernogolovka, Moscow Region, Russian Federation. E-mail: [email protected] cA. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Build. 4, 31 Leninsky prosp., 119071 Moscow, Russian Federation. dN. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991 Moscow, Russian Federation. The review is concerned with studies on peculiar features of supramolecular organization of phthalocyanines (Pc) bearing complex-forming substituents (15-crown-5, 2-oxyphenylphosphonic acid residues) in organized aqueous microheterogeneous media based on cationic and anionic surfactants, bile salts (BS) including sodium deoxycholate (SDC), as well as polyelectrolytes and amphiphilic polymers including a phosphate buffer (рН 7.4). Organized, SDC-based fluorescence-active phthalocyanine-containing hydrogels obtained for the first time are also considered. In vitro accumulation and localization of Pc in human cervical adenocarcinoma cells, HeLa, as well as the photochemical and sensitizing properties of Pc including light cytotoxicity and photoinduced generation of reactive oxygen species were demonstrated taking octa-crown-substituted magnesium phthalocyaninate as an example. Key words: supramolecular assembly, phthalocyanines, solubilization, crown ethers, 2-oxyphenylphosphonic acid, bile salts, surfactants, photosensitizer.
Introduction Supramolecular chemistry is a field of knowledge which studies self-organization processes involving molecules that are often structurally or functionally similar to biological molecules and resulting in the formation of supramolecular assemblies and other objects that held together through intermolecular interactions (hydrogen bonds, ion-ion, ion-dipole, van der Waals, —-stacking, СН—, hydrophobic, coordination interactions, etc.). The term "supramolecular chemistry" and the basic concepts were introduced by J.-M. Lehn in 1978.1 The energy of intermolecular interactions is much lower than that of covalent bonds in organic molecules and rarely reaches values of the order of 100 kJ mol–1. For instance, the energy of СН—interactions falls in the range of 0.84—10.5 kJ mol–1.2 Numerous weak noncovalent interactions stabilize supramolecular assemblies, being responsible for reversible * Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9—13, 2019, St. Petersburg, Russia).
character of molecular association (or self-organization)
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