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Quenching of Pyrene Fluorescence by Calix[4]arene and Calix[4]resorcinarenes

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Abstract

Interactions involving calixarene and its derivatives are of major importance due to their widespread applications as unique hosts. Fluorescence from a common probe pyrene is used to study interactions involving calix[4]resorcinarene [1a] and its tetra-morpholine derivative [1b] in 1 M aqueous NaOH. These compounds efficiently quench the pyrene fluorescence. A comparison with the fluorescence quenching behavior of N-methylmorpholine clearly indicates the presence of long-range interactions involving 1a and 1b; the interactions are specific to the calixarene molecular framework. This is not the case for a tetra-nitro-substituted calix[4]arene [2b], an electron/charge acceptor quencher, as p-nitrophenol also shows similar interactions with pyrene. Effectiveness of cesium as the quencher of pyrene fluorescence is reduced in the presence of electron/charge donating 1b; fluorescence enhancement is observed upon addition of cesium as the concentration of 1b is increased in the solution. The role of calixarene framework in interactions involving such compounds is established.

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Acknowledgements

We thank the Council of Scientific and Industrial Research, India and Department of Biotechnology, India for senior research fellowships to SP and AB; and Department of Science and Technology, Govt. of India for financial assistance. MA would like to recognize a fellowship from UGC, India.

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Authors and Affiliations

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

    Shubha Pandey, Maroof Ali, Anjali Bishnoi, Siddharth Pandey & H. M. Chawla

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

    Shubha Pandey & Amir Azam

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  1. Shubha Pandey
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  2. Maroof Ali
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  3. Anjali Bishnoi
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  4. Amir Azam
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  6. H. M. Chawla
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Correspondence to Amir Azam, Siddharth Pandey or H. M. Chawla.

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Pandey, S., Ali, M., Bishnoi, A. et al. Quenching of Pyrene Fluorescence by Calix[4]arene and Calix[4]resorcinarenes. J Fluoresc 18, 533–539 (2008). https://doi.org/10.1007/s10895-007-0296-8

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  • DOI: https://doi.org/10.1007/s10895-007-0296-8

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