Research Article

Solvatochromism of catechol derivatives – solute/solvent interactions

  1. Franziska Riedel,
  2. Stefan Spange*

Article first published online: 22 JUL 2012

DOI: 10.1002/poc.3003

Issue

Journal of Physical Organic Chemistry

Journal of Physical Organic Chemistry

Volume 25, Issue 12, pages 1261–1268, December 2012

Additional Information

How to Cite

Riedel F. and Spange S. (2012), Solvatochromism of catechol derivatives – solute/solvent interactions, Journal of Physical Organic Chemistry. DOI: 10.1002/poc.3003

Author Information

  1. Department of Polymer Chemistry, Institute of Chemistry, Faculty of Natural Science, University of Technology Chemnitz, Chemnitz, Germany

* Stefan Spange, Department of Polymer Chemistry, Institute of Chemistry, Faculty of Natural Science, University of Technology Chemnitz, Strasse der Nationen 62, D-09111 Chemnitz, Germany.
E-mail: stefan.spange@chemie.tu-chemnitz.de

Publication History

  1. Issue published online: 7 JAN 2013
  2. Article first published online: 22 JUL 2012
  3. Manuscript Accepted: 20 JUN 2012
  4. Manuscript Revised: 13 JUN 2012
  5. Manuscript Received: 5 MAR 2012

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Keywords:

  • catechol;
  • donor–acceptor systems;
  • hydrogen bonds;
  • linear solvation energy correlation analysis;
  • solvatochromism

The solvatochromism of nine push–pull substituted catechol derivatives has been studied in a set of 39 various solvents. The influence of successive methyl substitution at the catechol OH groups on the extent of the solvatochromic shift has been investigated. The positive solvatochromism of 2-(3,4-dihydroxybenzylidene)-2H-indene-1,3-dione amounts 4360 cm–1, which ranges from toluene to hexamethyl-phosphoric triamide. To the best of our knowledge, it is one of the largest positive solvatochromic extent measured for a positive solvatochromic dye, comparable with Brooker's thiobarbituric acid with an extent of 4400 cm–1. The detailed analyses of the solvatochromism were carried out by alternatively using the Kamlet–Taft and Catalán solvent parameters to achieve information of dipolarity versus polarizability effects of solvent upon solvatochromic properties. In solvents with high β values such as alcohols (0.66 < β < 0.90), amides (0.48 < β < 0.80), dimethyl sulfoxide (β = 0.76), tetramethyl urea (β = 0.80) and hexamethyl-phosphoric triamide (β = 1.05) UV–Vis absorption spectra show two separate λmax, which are caused by a deprotonation reaction. The solvatochromic behaviour of the anionic species is compared with those of the catechol derivatives. Copyright © 2012 John Wiley & Sons, Ltd.

Featured Compounds

Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2a
Molecular Weight:186.1668
Molecular Formula:C10H6N2O2
InChIKey:VTJXFTPMFYAJJU-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:200.1934
Molecular Formula:C11H8N2O2
InChIKey:WKTJJISTXUHPEQ-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:214.22
Molecular Formula:C12H10N2O2
InChIKey:RENWPBQTHLAKLS-UHFFFAOYSA-N
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3a
Molecular Weight:266.2482
Molecular Formula:C16H10O4
InChIKey:HNKTYJVAICSKHB-UHFFFAOYSA-N
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Compound 3a-
Molecular Weight:266.2482
Molecular Formula:C16H10O4
InChIKey:HNKTYJVAICSKHB-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:280.2748
Molecular Formula:C17H12O4
InChIKey:NPHKQWBQYOBTKH-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:294.3014
Molecular Formula:C18H14O4
InChIKey:OVHSLRSKIAKFOH-UHFFFAOYSA-N
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4a
Molecular Weight:314.2943
Molecular Formula:C19H10N2O3
InChIKey:BUPZGSGQLRFMDA-CHHVJCJISA-N
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Compound 4b
Molecular Weight:328.3209
Molecular Formula:C20H12N2O3
InChIKey:ZDXLKKDMAILVMC-PXNMLYILSA-N
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Compound I
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound II
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1a
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:Not Available
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Compound 1b
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:MWOOGOJBHIARFG-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:WJUFSDZVCOTFON-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:342.3475
Molecular Formula:C21H14N2O3
InChIKey:PZNGQHOAEXXOHT-MFOYZWKCSA-N
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