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Effect of Solvents and pH on β-Cyclodextrin Inclusion Complexation of 2,4-Dihydroxyazobenzene and 4-Hydroxyazobenzene

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Abstract

The spectral characteristics of 2,4-dihydroxyazobenzene (DHAB, sudan orange G) and 4-hydroxyazobenzene (HAB) have been studied in various solvents, different hydrogen ion and β-cyclodextrin (β-CD) concentrations, and are compared with azobenzene (AB). The inclusion complexes of the above molecules with β-CD were analyzed by UV-vis spectrometry, flourometry, FT-IR, 1H NMR, SEM and DFT methods. The solvent study shows that only the azo form is present in DHAB and HAB molecules. The unusually large red shift observed in acidic solutions indicates both molecules exhibit azo-hydrazo tautomerization. In the β-CD solutions, the increase in fluorescence intensity and large bathochromic shift in the S1 state indicates that DHAB and HAB form 2:2 inclusion complexes, whereas AB forms a 1:1 inclusion complex.

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Authors and Affiliations

  1. Department of Chemistry, Scott Christian College, Nagercoil, 629 002, India

    J. Premakumari & G. Allan Gnana Roy

  2. Department of Chemistry, Annamalai University, Annamalai Nagar, 608 002, Tamilnadu, India

    A. Antony Muthu Prabhu, G. Venkatesh, V. K. Subramanian & N. Rajendiran

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  1. J. Premakumari
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10953_2010_9639_MOESM1_ESM.doc

Supplementary Photographs for: Experimental and theoretical thermodynamic studies of the adsorption of polyhalogenated organic compounds from aqueous solution by chemically modified multi-walled carbon nanotubes. (DOC 8.44MB)

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Premakumari, J., Roy, G.A.G., Prabhu, A.A.M. et al. Effect of Solvents and pH on β-Cyclodextrin Inclusion Complexation of 2,4-Dihydroxyazobenzene and 4-Hydroxyazobenzene. J Solution Chem 40, 327–347 (2011). https://doi.org/10.1007/s10953-010-9639-1

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