Dissimilar Associates of Dyes in Aqueous Solutions: Experimental Study and Computer Simulation

Serghey Shapovalov

Abstract


Dissimilar cation-anionic association of dyes («cyanine+oxyxanthene», «cyanine+sulfonepthalein») has been regularly investigated in aqueous solutions. Experimental (by spectrophotometry) and theoretical (by semiempirical) methods were used. The basic regularities of association processes have been discussed. It is shown that the change in the stability of associates has a systematic character both in the series of singly charged and doubly charged anions. The experimentally determined values (of equilibrium constant of association) and simulated values (of standard enthalpy of hydration of associates) are mutually consistent. The standard enthalpy of formation and the most probable structures of associates have been determined.


Keywords


dissimilar associates; dyes; simulation; solutions; enthalpy of formation; spectroscopy

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Ishchenko A, Shapovalov S. Heterogeneous Association of the Ions of Dyes in Solutions (Review). Journal of Applied Spectroscopy 2004;71(5):605-629. https://doi.org/10.1023/b:japs.0000049618.42857.0a

Yamaguchi A, Kometani N, Yonezawa Y. Luminescence Properties of the Mixed J-Aggregate of Oxacyanine Dye and Thiacyanine Dye. Formation of a Persistence-Type Aggregate. The Journal of Physical Chemistry B 2005;109(4):1408-1414. https://doi.org/10.1021/jp0405557

Shapiro B. Molecular assemblies of polymethine dyes. Russian Chemical Reviews 2006;75(5):433-456. https://doi.org/10.1070/rc2006v075n05abeh001208

Kaliteevskaya E, Krutyakova V, Razumova T, Starovoitov A. The Influence of the Molecular Structure of Cyanine Dye on the Component Composition of Molecular Layers. Optics and Spectroscopy 2016;120(3):482-491. https://doi.org/10.1134/s0030400x16030127

Arslanov V. Polymer monolayers and Langmuir–Blodgett films. Polythiophenes. Russian Chemical Reviews 2000;69(10):883-898. https://doi.org/10.1070/rc2000v069n10abeh000612

Murakami K. Thermodynamic and kinetic aspects of self-association of dyes in aqueous solution. Dyes and Pigments 2002;53(1):31-43. https://doi.org/10.1016/s0143-7208(01)00104-8

Hoeben F, Jonkheijm P, Meijer E, Schenning A. About Supramolecular Assemblies of π-Conjugated Systems. Chemical Reviews 2005;105(4):1491-1546. https://doi.org/10.1021/cr030070z

Chen Z, Lohr A, Saha-Möller C, Würthner F. Self-assembled π-stacks of functional dyes in solution: structural and thermodynamic features. Chem. Soc. Rev. 2009;38(2):564-584. https://doi.org/10.1039/b809359h

Setiawan D, Kazaryan A, Martoprawiro M, Filatov M. A first principles study of fluorescence quenching in rhodamine B dimers: how can quenching occur in dimeric species?. Physical Chemistry Chemical Physics 2010;12(37):11238. https://doi.org/10.1039/c004573j

Rehm T, Schmuck C. Ion-pair induced self-assembly in aqueous solvents. Chemical Society Reviews 2010;39(10):3597. https://doi.org/10.1039/b926223g

Shapovalov SA. The association processes of protolytic forms of dyes in solutions. Self-association. Kharkiv: Brovin Publishing House; 2012, 218 Р.

Pronkin P, Tatikolov A. Study of cis-trans equilibrium of oxacarbocyanine dyes in solution and in a complex with DNA. High Energy Chemistry 2012;46(4):253-258. https://doi.org/10.1134/s0018143912040157

Shahid M, Shahid-ul-Islam , Mohammad F. Recent advancements in natural dye applications: a review. Journal of Cleaner Production 2013;53:310-331. https://doi.org/10.1016/j.jclepro.2013.03.031

Hu L, Yuan H, Li Q, Jin J, Chang W, Yan Z. Spectral Properties of a Water-Soluble Squaraine Dye and Its Application in Cell Fluorescent Imaging. Journal of Applied Spectroscopy 2015;82(4):665-668. https://doi.org/10.1007/s10812-015-0160-6

Maskevich A, Lavysh A, Kuznetsova I, Sulatskaya A, Turoverov K. Spectral Manifestations of Thioflavin T Aggregation. Journal of Applied Spectroscopy 2015;82(1):33-39. https://doi.org/10.1007/s10812-015-0060-9

Tarasevich Y, , Tryfonova M, . Adsorption of Organic Anions and Cations from Aqueous Solutions on Organosubstituted Layered Silicates. Himia, Fizika ta Tehnologia Poverhni 2015;6(1):56-66. https://doi.org/10.15407/hftp06.01.056

Malyukin YV, Yefimova SL, Tkacheva ТN, Grygorova GV. ORDERED ADSORPTION OF ORGANIC MOLECULES ON INORGANIC NANOPARTICLES. Visnik Nacional'noi' akademii' nauk Ukrai'ni 2015;(06):34-42. https://doi.org/10.15407/visn2015.06.034

Tkachenko SV, Chernikova EY, Minkovska S, Deligeorgiev T, Fedorova OA, Fedorov YV. Multicomponent molecular ensembles of bysstyryl dye with cucurbit[7]uril: structure and spectral characteristics. Successes in Chemistry and Chemical Technology (Rus.). 2015; 29(7): 117-120.

Baranovsky SF, Buchelnikov AS, Chernyshev DN, Astafieva DA. Study of the association of biologically active heterogeneous molecules. Topical Issues of Biological Physics and Chemistry (Russ.). 2016; 1(1): 164-169.

Pronkin P, Tatikolov A, . Formation of J-Aggregates of an Anionic Oxacarbocyanine Dye Upon Interaction with Proteins and Polyelectrolytes. Journal of Applied Spectroscopy 2017;84(2):217-224. https://doi.org/10.1007/s10812-017-0454-y

Shestopalova A. The investigation of the association of caffeine and actinocin derivatives in aqueous solution: A molecular dynamics simulation. Journal of Molecular Liquids 2006;127(1-3):113-117. https://doi.org/10.1016/j.molliq.2006.03.045

Ovchinnikov D, Baranovsky S, Rozvadovska A, Rogova O, Veselkov K, Ermolaev D, Parkes H, Davies D, Evstigneev M. Structural Basis for the Binding Affinity of a Homologous Series of Synthetic Phenoxazone Drugs with DNA: NMR and Molecular Mechanics Analysis. Journal of Biomolecular Structure and Dynamics 2007;24(5):443-453. https://doi.org/10.1080/07391102.2007.10507132

Shapovalov S, Samoilov E. Regularities of homo- and heteroassociation of the pinacyanol cation in aqueous solution. Russian Chemical Bulletin 2008;57(7):1405-1415. https://doi.org/10.1007/s11172-008-0183-8

Lipatova IM, Mezina EA, Yusova AA. Spectrophotometric research of chitosan complexing with phthalocyanine dyes. Proceedings of the Ufa Scientific Center of the Russian Academy of Sciences (Rus.). 2016;3(1):53-55.

Shapovalov S, Koval V, Chernaya T, Pereverzev A, Derevyanko N, Ishchenko A, Mchedlov-Petrossyan N. Association of indopolymethine cyanine cations with anions of sulfonephthalein and xanthene dyes in water. Journal of the Brazilian Chemical Society 2005;16(2):232-240. https://doi.org/10.1590/s0103-50532005000200017

Dewar M, Storch D. Development and use of quantum molecular models. 75. Comparative tests of theoretical procedures for studying chemical reactions. Journal of the American Chemical Society 1985;107(13):3898-3902. https://doi.org/10.1021/ja00299a023

Astakhov SA, Baranov VI, Gribov LA. Theory and methods of computational vibronic spectroscopy. New York: Nova Science Publishers; 2008, 83 P.

Stewart J. Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters. Journal of Molecular Modeling 2012;19(1):1-32. https://doi.org/10.1007/s00894-012-1667-x




DOI: https://doi.org/10.17721/fujcV5I2P30-39

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