Lipophilic contributions to the solvatochromism of analogous betaines

被引：9

作者：

Caroli Rezende, Marcos ^{[1
]}

Onate, Ruben ^{[1
]}

Nunez, Gabriel ^{[1
]}

Dominguez, Moises ^{[1
]}

Mascayano, Carolina ^{[1
]}

机构：

[1] Univ Santiago Chile, Fac Quim & Biol, Santiago, Chile

来源：

DYES AND PIGMENTS | 2009年 / 83卷 / 03期

关键词：

Lipophilicity; Solvatochromic phenolate betaines; Dynamics simulation; PYRIDINIUM N-PHENOLATE; MOLECULAR-DYNAMICS; SOLVENT POLARITIES; PI-STAR; MICELLES; ALPHA; DYES; PYRIDONES; PROBE;

D O I：

10.1016/j.dyepig.2009.06.011

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A pair of solvatochromic phenolate betaines that differed only in their lipophilicity was synthesized. Their solvatochromic responses in pure solvents, in a DMSO-MeOH solvent mixture as well as in micellar solutions were different, an observation which confirmed the fact that sensor lipophilicity contributes to the interpretation of solvatochromism. Quantum mechanical calculations reproduced the observed spectral differences. Molecular dynamics simulations shed light on the solute-solvent interactions responsible for their differences in solvent mixtures. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：391 / 395

页数：5

共 21 条

[1]

*ACC, 1998, INS US GUID

[2] On the solvatochromic reversal of merocyanine dyes .2. An experimental and semi-empirical study of the solvatochromism of alpha- and gamma-vinylogous pyridones [J].

Aliaga, C ;

Galdames, JS ;

Rezende, MC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (05) :1055-1058

[3] Hydrophobic interaction of amphiphilic hemicyanine dyes with cationic and anionic surfactant micelles [J].

Awan, MA ;

Shah, SS .

COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 1997, 122 (1-3) :97-101

[4] A WELL-BEHAVED ELECTROSTATIC POTENTIAL BASED METHOD USING CHARGE RESTRAINTS FOR DERIVING ATOMIC CHARGES - THE RESP MODEL [J].

BAYLY, CI ;

CIEPLAK, P ;

CORNELL, WD ;

KOLLMAN, PA .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (40) :10269-10280

[5] CHARMM - A PROGRAM FOR MACROMOLECULAR ENERGY, MINIMIZATION, AND DYNAMICS CALCULATIONS [J].

BROOKS, BR ;

BRUCCOLERI, RE ;

OLAFSON, BD ;

STATES, DJ ;

SWAMINATHAN, S ;

KARPLUS, M .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (02) :187-217

[6]

Frisch M.J., 1998, GAUSSIAN 98

[7] The preparation and solvatochromic properties of vinylogous α-pyridones [J].

Galdames, JS ;

Rezende, MC .

JOURNAL OF CHEMICAL RESEARCH, 1998, (03) :106-107

[8] An amphiphilic hemicyanine dye employed as a sensitive probe of water in reverse AOT micelles [J].

Hof, M ;

Lianos, P ;

Laschewsky, A .

LANGMUIR, 1997, 13 (08) :2181-2183

[9]

HUMPHREY W, 1966, J MOL GRAPHICS, V14, P33

[10] LINEAR SOLVATION ENERGY RELATIONSHIPS .23. A COMPREHENSIVE COLLECTION OF THE SOLVATOCHROMIC PARAMETERS, PI-STAR, ALPHA AND BETA, AND SOME METHODS FOR SIMPLIFYING THE GENERALIZED SOLVATOCHROMIC EQUATION [J].

KAMLET, MJ ;

ABBOUD, JLM ;

ABRAHAM, MH ;

TAFT, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2877-2887

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