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Competitive Self and Induced Aggregation of Calix[4]arene Ethers and Their Interaction with Pinacyanol Chloride and Methylene Blue in Nonaqueous Media

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Abstract

Long chain calix[4]arene ethers have been examined for aggregation in nonaqueous solvents by using UV-vis molecular absorbance spectroscopy. It has been observed that tetraalkylated (alkyl = hexadecyl and octadecyl, respectively) calix[4]arene ethers tend to aggregate in chloroform and tetrahydrofuran, possibly via π–π stacking interactions of the phenyl moieties, and the aggregation process appears to be facilitated by the alkyl chains. The analogous dialkylated compounds do not show any self-aggregation, plausibly due to strong hydrogen bonding between the –OH and the –O– of calix aryl ether which seems to disrupt the aggregation process. Addition of the anionic surfactant sodium dodecylsulfate (SDS) appears to hinder the aggregation process in nonpolar chloroform but the same surfactant facilitates aggregation in the polar tetrahydrofuran. The cationic surfactant (cetyltrimethyl ammonium bromide) and the nonionic surfactant (Brij-35) have no effect on this aggregation process. Unexpectedly, SDS induces aggregation of dialkylated calix[4]arene ethers in chloroform. It has been observed that the aggregated form of the tetraalkylated calix[4]arene ethers tend to increase the dimerization efficiency of cationic dyes (pinacyanol chloride and methylene blue) in chloroform.

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Authors and Affiliations

  1. Department of Chemistry, Jamia Millia Islamia, New Delhi, 110028, India

    Shubha Pandey, Jyotsna R. Kar & Amir Azam

  2. Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India

    Shubha Pandey, Jyotsna R. Kar, Siddharth Pandey & H. M. Chawla

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  1. Shubha Pandey
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  2. Jyotsna R. Kar
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  5. H. M. Chawla
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Correspondence to Siddharth Pandey.

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Pandey, S., Kar, J.R., Azam, A. et al. Competitive Self and Induced Aggregation of Calix[4]arene Ethers and Their Interaction with Pinacyanol Chloride and Methylene Blue in Nonaqueous Media. J Solution Chem 39, 107–120 (2010). https://doi.org/10.1007/s10953-009-9489-x

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