CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2004, Vol. 76, No. 10, pp. 1903-1919

http://dx.doi.org/10.1351/pac200476101903

Pyridinium N-phenolate betaine dyes as empirical indicators of solvent polarity: Some new findings

C. Reichardt

Department of Chemistry, Philipps University, Hans-Meerwein-Strasse, D-35032 Marburg, Germany

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Cerón-Carrasco José P., Jacquemin Denis, Laurence Christian, Planchat Aurélien, Reichardt Christian, Sraïdi Khadija: Solvent polarity scales: determination of new E T (30) values for 84 organic solvents. J. Phys. Org. Chem. 2014, n/a. <http://dx.doi.org/10.1002/poc.3293>
  • Babai Arash, Kopiec Gabriel, Lackmann Anastasia, Mallick Bert, Pitula Slawomir, Tang Sifu, Mudring Anja-Verena: Eu3+ as a dual probe for the determination of IL anion donor power: A combined luminescence spectroscopic and electrochemical approach. Journal of Molecular Liquids 2014. <http://dx.doi.org/10.1016/j.molliq.2014.03.005>
  • Aloïse Stéphane, Pawlowska Zuzanna, Poizat Olivier, Buntinx Guy, Perrier Aurélie, Maurel François, Ohkawa Kazuhiro, Kimoto Atsushi, Abe Jiro: Excited-state dynamics of thiophene substituted betaine pyridinium compounds. Phys. Chem. Chem. Phys. 2014, 16, 1460. <http://dx.doi.org/10.1039/c3cp53614a>
  • Oliveira Elisabete, Baptista Rosa M. F., Costa Susana P. G., Raposo M. Manuela M., Lodeiro Carlos: Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials. Photochem. Photobiol. Sci. 2014, 13, 492. <http://dx.doi.org/10.1039/c3pp50352f>
  • Afri Michal, Gottlieb Hugo E., Frimer Aryeh A.: Reichardt’s dye: the NMR story of the solvatochromic betaine dye. Can. J. Chem. 2014, 92, 128. <http://dx.doi.org/10.1139/cjc-2013-0349>
  • Langhals Heinz, Braun Patricia, Dietl Christian, Mayer Peter: How Many Molecular Layers of Polar Solvent Molecules Control Chemistry? The Concept of Compensating Dipoles. Chem. Eur. J. 2013, 19, 13511. <http://dx.doi.org/10.1002/chem.201300770>
  • Gharib Farrokh, Shamel Ali, Jaberi Fatemeh, Farajtabar Ali: Spectral Investigations of Preferential Solvation and Solute–Solvent Interactions of Free Base and Protonated 5,10,15,20-Tetrakis(4-trimethyl-ammonio-phenyl)-porphine Tetratosylate in Aqueous Organic Mixed Solvents. J Solution Chem 2013, 42, 1083. <http://dx.doi.org/10.1007/s10953-013-0007-9>
  • Wu Changzeng, Wang Jianji, Li Zhiyong, Jing Jun, Wang Huiyong: Relative hydrophobicity between the phases and partition of cytochrome-c in glycine ionic liquids aqueous two-phase systems. Journal of Chromatography A 2013, 1305, 1. <http://dx.doi.org/10.1016/j.chroma.2013.06.066>
  • Menzel Roberto, Kupfer Stephan, Mede Ralf, Görls Helmar, González Leticia, Beckert Rainer: Synthesis, properties and quantum chemical evaluation of solvatochromic pyridinium-phenyl-1,3-thiazol-4-olate betaine dyes. Tetrahedron 2013, 69, 1489. <http://dx.doi.org/10.1016/j.tet.2012.12.016>
  • Lo Wei-Jen, Chen Yi-Hui, Sung Kuangsen: Twisting-Based Spectroscopic Measure of Solvent Polarity: The PT Scale. J. Org. Chem. 2013, 78, 5925. <http://dx.doi.org/10.1021/jo400586w>
  • Shakerizadeh-Shirazi Fatemeh, Hemmateenejad Bahram, Mehranpour Abdol Mohammad: Determination of the empirical solvent polarity parameter ET(30) by multivariate image analysis. Anal. Methods 2013, 5, 891. <http://dx.doi.org/10.1039/c2ay26185e>
  • Chiappe Cinzia, Pomelli Christian Silvio: The first solvation shell of Reichardt’s dye in ionic liquids: a semiempirical study. Theor Chem Accounts 2012, 131, 1195. <http://dx.doi.org/10.1007/s00214-012-1195-x>
  • Jacques Patrice, Graff Bernadette, Diemer Vincent, Ay Emel, Chaumeil Hélène, Carré Christiane, Malval Jean-Pierre: Negative solvatochromism of a series of pyridinium phenolate betaine dyes with increasing steric hindrance. Chemical Physics Letters 2012, 531, 242. <http://dx.doi.org/10.1016/j.cplett.2012.02.018>
  • Moita Maria-Luísa C. J., Santos Ângela F. S., Silva João F. C. C., Lampreia Isabel M. S.: Polarity of Some [NR1R2R3R4]+[Tf2N]− Ionic Liquids in Ethanol: Preferential Solvation versus Solvent–Solvent Interactions. J. Chem. Eng. Data 2012, 57, 2702. <http://dx.doi.org/10.1021/je300563k>
  • Burke Kathryn, Riccardi Caterina, Buthelezi Thandi: Thermosolvatochromism of Nitrospiropyran and Merocyanine Free and Bound to Cyclodextrin. Chem B 2012, 116, 2483. <http://dx.doi.org/10.1021/jp208023r>
  • Malval Jean-Pierre, Chaumeil Hélène, Rettig Wolfgang, Kharlanov Vladimir, Diemer Vincent, Ay Emel, Morlet-Savary Fabrice, Poizat Olivier: Excited-state dynamics of phenol–pyridinium biaryl. PCCP 2012, 14, 562. <http://dx.doi.org/10.1039/c1cp22829c>
  • Alam Md. Mehboob, Chattopadhyaya Mausumi, Chakrabarti Swapan: Solvent induced channel interference in the two-photon absorption process—a theoretical study with a generalized few-state-model in three dimensions. PCCP 2012, 14, 1156. <http://dx.doi.org/10.1039/c1cp22849h>
  • D'Anna Francesca, Marullo Salvatore, Vitale Paola, Noto Renato: The Effect of the Cation π-Surface Area on the 3D Organization and Catalytic Ability of Imidazolium-Based Ionic Liquids. Eur J Org Chem 2011, 2011, 5681. <http://dx.doi.org/10.1002/ejoc.201100763>
  • Fodor Krisztina, Tomescova Vladimira, Kőszegi Tamás, Kron Ivan, Perjési Pál: (E)-2-Benzylidenecyclanones: Part VI. Solvent effect on the UV and fluorescence properties of some chalcones and their cyclic analogues. Interaction of 4-dimethylaminochalcones with bovine and human serum albumin: a UV–vis study. Monatshefte für Chemie 2011, 142, 463. <http://dx.doi.org/10.1007/s00706-011-0463-0>
  • Espinosa M., Pacheco S., Vargas S., Estevez M., Llanos M.E., Rodríguez R.: Homogeneous and heterogeneous catalytic behavior of Ni-porphyrines immobilized in SBA-15 for the esterification of DMT. Applied Catalysis A: General 2011, 401, 119. <http://dx.doi.org/10.1016/j.apcata.2011.05.006>
  • Rezende Marcos Caroli, Dominguez Moisés, Aracena Andrés, Millán Daniela: Solvatochromism and electrophilicity. Chemical Physics Letters 2011, 514, 267. <http://dx.doi.org/10.1016/j.cplett.2011.08.070>
  • Farajtabar Ali, Jaberi Fatemeh, Gharib Farrokh: Preferential solvation and solvation shell composition of free base and protonated 5, 10, 15, 20-tetrakis(4-sulfonatophenyl)porphyrin in aqueous organic mixed solvents. Spectochim Acta A 2011, 83, 213. <http://dx.doi.org/10.1016/j.saa.2011.08.020>
  • Hallett Jason P., Welton Tom: Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2. Chem. Rev. 2011, 111, 3508. <http://dx.doi.org/10.1021/cr1003248>
  • Murugan N. Arul: Modeling Solvatochromism of a Quinolinium Betaine Dye in Water Solvent Using Sequential Hybrid QM/MM and Semicontinuum Approach. Chem B 2011, 115, 1056. <http://dx.doi.org/10.1021/jp1049342>
  • Klein Regina, Zech Oliver, Maurer Eva, Kellermeier Matthias, Kunz Werner: Oligoether Carboxylates: Task-Specific Room-Temperature Ionic Liquids. Chem B 2011, 115, 8961. <http://dx.doi.org/10.1021/jp200624g>
  • Chiappe Cinzia, Pomelli Christian Silvio, Rajamani Sunita: Influence of Structural Variations in Cationic and Anionic Moieties on the Polarity of Ionic Liquids. Chem B 2011, 115, 9653. <http://dx.doi.org/10.1021/jp2045788>
  • Fidale Ludmila C., Ißbrücker Constance, Silva Priscilla L., Lucheti Camila M., Heinze Thomas, El Seoud Omar A.: Probing the dependence of the properties of cellulose acetates and their films on the degree of biopolymer substitution: use of solvatochromic indicators and thermal analysis. Cellulose 2010, 17, 937. <http://dx.doi.org/10.1007/s10570-010-9438-2>
  • Katkevica S., Zicmanis A., Mekss P.: Imidazolium and pyridinium salts – solvents influencing the rate and direction of the Fries, Beckmann, and Claisen rearrangements. Chem Heterocycl Compd 2010, 46, 158. <http://dx.doi.org/10.1007/s10593-010-0487-0>
  • Shekhovtsov Sergey V., Mchedlov-Petrossyan Nikolay O., Reichardt Christian: A new application of solvatochromic pyridinium-N-phenolate betaine dyes: examining the electrophilicity of lanthanide shift reagents. Tetrahetron Lett 2010, 51, 4347. <http://dx.doi.org/10.1016/j.tetlet.2010.06.057>
  • Bartosik Joanna, Mudring Anja-Verena: [Ni(tmen)(acac)][B(Ph)4] a probe for the anion basicity of ionic liquids. Phys Chem Chem Phys 2010, 12, 4005. <http://dx.doi.org/10.1039/b920530f>
  • Pitula Slawomir, Mudring Anja-Verena: Optical basicity of ionic liquids. Phys Chem Chem Phys 2010, 12, 7056. <http://dx.doi.org/10.1039/b925606g>
  • Zech Oliver, Hunger Johannes, Sangoro Joshua R., Iacob Ciprian, Kremer Friedrich, Kunz Werner, Buchner Richard: Correlation between polarity parameters and dielectric properties of [Na][TOTO]—a sodium ionic liquid. Phys Chem Chem Phys 2010, 12, 14341. <http://dx.doi.org/10.1039/c0cp00840k>
  • Adam Claudia G., Fortunato Graciela G., Mancini Pedro M.: Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1. J Phys Org Chem 2009, 22, 460. <http://dx.doi.org/10.1002/poc.1501>
  • Trivedi Shruti, Sarkar Abhra, Pandey Siddharth: Solvatochromic absorbance probe behavior within 1-butyl-3-methylimidazolium hexafluorophosphate+propylene carbonate: Preferential solvation or solvent–solvent interaction?. Chem Eng J 2009, 147, 36. <http://dx.doi.org/10.1016/j.cej.2008.11.014>
  • Zimmermann-Dimer Lizandra Maria, Reis Dalci Clair, Machado Clodoaldo, Machado Vanderlei Gageiro: Chromogenic anionic chemosensors based on protonated merocyanine solvatochromic dyes in trichloromethane and in trichloromethane–water biphasic system. Tetrahedron 2009, 65, 4239. <http://dx.doi.org/10.1016/j.tet.2009.03.049>
  • Linder Thomas, Sundermeyer Jörg: Three novel anions based on pentafluorophenyl amine combined with two new synthetic strategies for the synthesis of highly lipophilic ionic liquids. Chem Commun 2009, 2914. <http://dx.doi.org/10.1039/b823153b>
  • Mancini P. M., Fortunato G. G., Adam C. G., Vottero L. R.: Solvent effects on chemical processes: new solvents designed on the basis of the molecular–microscopic properties of (molecular solvent + 1,3-dialkylimidazolium) binary mixtures. J Phys Org Chem 2008, 21, 87. <http://dx.doi.org/10.1002/poc.1227>
  • Fracaroli Alejandro M., Silva O. Fernando, Granados Alejandro M., de Rossi Rita H.: 3H-1,2-Dithiole-3-thione derivatives as novel solvatochromic dyes. J Phys Org Chem 2008, 21, 1007. <http://dx.doi.org/10.1002/poc.1416>
  • Wan Jiandi, Ferreira Amy, Xia Wei, Chow Chak Him, Takechi Kensuke, Kamat Prashant V., Jones Guilford, Vullev Valentine I.: Solvent dependence of the charge-transfer properties of a quaterthiophene–anthraquinone dyad. J Photochem Photobiol A Chem 2008, 197, 364. <http://dx.doi.org/10.1016/j.jphotochem.2008.01.016>
  • Nishiyama Satoko, Tajima Masahiro, Yoshida Yasuhiko: Environmental Effects on Photochemical Properties of Betaine Dyes in Rigid Media. Molecular Crystals and Liquid Crystals 2008, 492, 130/[494]. <http://dx.doi.org/10.1080/15421400802331117>
  • Niewodniczański Wawrzyniec, Bartkowiak Wojciech: Theoretical study of geometrical and nonlinear optical properties of pyridinum N-phenolate betaine dyes. J Mol Model 2007, 13, 793. <http://dx.doi.org/10.1007/s00894-007-0198-3>
  • Heger Dominik, Klán Petr: Interactions of organic molecules at grain boundaries in ice: A solvatochromic analysis. J Photochem Photobiol A Chem 2007, 187, 275. <http://dx.doi.org/10.1016/j.jphotochem.2006.10.012>
  • Singh Pallavi, Pandey Siddharth: Solute?solvent interactions within aqueous poly(ethylene glycol): solvatochromic probes for empirical determination and preferential solvation. Green Chem 2007, 9, 254. <http://dx.doi.org/10.1039/b603210a>
  • Ali Maroof, Sarkar Abhra, Tariq Mohammad, Ali Anwar, Pandey Siddharth: Dilute aqueous 1-butyl-3-methylimidazolium hexafluorophosphate: properties and solvatochromic probe behavior. Green Chem 2007, 9, 1252. <http://dx.doi.org/10.1039/b704843b>
  • Nishiyama Satoko, Tajima Masahiro, Yoshida Yasuhiko: Effects of Molecular Structure on Luminescent Properties of Betaine Dyes. Mol Cryst Liq Cryst 2007, 472, 33/[423]. <http://dx.doi.org/10.1080/15421400701544810>
  • El Seoud Omar A., Siviero Fábio: Kinetics of the pH-independent hydrolyses of 4-nitrophenyl chloroformate and 4-nitrophenyl heptafluorobutyrate in water-acetonitrile mixtures: consequences of solvent composition and ester hydrophobicity. J Phys Org Chem 2006, 19, 793. <http://dx.doi.org/10.1002/poc.1081>
  • Bentley T. William, Garley Michael S.: Correlations and predictions of solvent effects on reactivity: some limitations of multi-parameter equations and comparisons with similarity models based on one solvent parameter. J Phys Org Chem 2006, 19, 341. <http://dx.doi.org/10.1002/poc.1084>
  • Reis Dalci C., Machado Clodoaldo, Machado Vanderlei G.: An anionic chromogenic sensor based on protonated Reichardt’s pyridiniophenolate. Tetrahetron Lett 2006, 47, 9339. <http://dx.doi.org/10.1016/j.tetlet.2006.10.109>
  • Sarkar Abhra, Pandey Siddharth: Solvatochromic Absorbance Probe Behavior and Preferential Solvation in Aqueous 1-Butyl-3-methylimidazolium Tetrafluoroborate. J Chemical & Engineering Data 2006, 51, 2051. <http://dx.doi.org/10.1021/je0601560>
  • Nishiyama Satoko, Aikawa Shunichi, Yoshida Yasuhiko, Tajima Masahiro: Luminescence of Betaine-30 Dispersed in Polymeric Solids. Mol Liq Cryst 2006, 462, 257. <http://dx.doi.org/10.1080/15421400601013411>
  • Reichardt Christian: Pyridinium N-Phenoxide Betaine Dyes and Their Application to the Determination of Solvent Polarities. Part 28. ChemInform 2005, 36. <http://dx.doi.org/10.1002/chin.200509285>
  • Zoon Peter D., Brouwer Albert M.: Paradoxical Solvent Effects on the Absorption and Emission Spectra of Amino-Substituted Perylene Monoimides. Chem Eur J of Chem Phys 2005, 6, 1574. <http://dx.doi.org/10.1002/cphc.200500127>
  • Batchelor Stephen N., Oakes John: New solvent scale applicable to microheterogeneous media. J Phys Org Chem 2005, 18, 899. <http://dx.doi.org/10.1002/poc.961>
  • Martins Clarissa T., Lima Michelle S., El Seoud Omar A.: A novel, convenient, quinoline-based merocyanine dye: probing solvation in pure and mixed solvents and in the interfacial region of an anionic micelle. J Phys Org Chem 2005, 18, 1072. <http://dx.doi.org/10.1002/poc.975>
  • Reichardt Christian: Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes. Green Chem 2005, 7, 339. <http://dx.doi.org/10.1039/b500106b>