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Most Efficient Tris(3-Aminopropyl) Amine Based Electron Deficient Tripodal Receptor for Azide

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Abstract

Investigation on strength of the tris(2-amino ethyl) amine and tris (3-amino propyl) amine backboned tripodal receptors, L and L1 (incorporated with tripodal C3ν frame, thio urea-amide linkage and π-hole assisting functionality) which are premeditated to explore the prospect for a particular anion recognition are studied. UV-Vis, 1H- NMR, and IR spectroscopy studies indicates that both the receptors sensing azide anion, colorimetrically and binds azide anion stronger than any other anions such as acetate, and cyanide. In particular the receptor L1 shows the highest binding strength towards azide anion. To the best of our knowledge this is the first receptor showing highest binding ability with azide anion. We used Molecular Electrostatic Potential Surface analyses to support our spectroscopic findings. The association constant and limits of detection for receptor L1 with azide is found to be 8.4X105M−1 and 3.16X10−6 M respectively. The observed highest binding strength of L1 with azide is, could be due to the cooperative effect of extended traditional hydrogen bonding via thiourea-amide functionality, anion-π interaction and C3ν suitable framework.

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Acknowledgements

This work is financially supported by DST-SERB, India under Early Career Research Award (ECR/2015/000318).

V. J acknowledges CSIR-HRDG-INDIA for a S.R.F. (122270/2K19/1). V. J., and M. K acknowledge Kalasalingam University (KARE) for PhD fellowship. The authors acknowledge I.R.C, KARE for providing Instrumentation facilities. The authors thank Dr. Shasi Anand, The Vice-President of Kalasalingam University, (KARE) for his constant support.

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Authors and Affiliations

  1. International Research Centre, Centre for Supramolecular Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar Krishnankoil, Srivilliputtur, Tamil Nadu, 626 126, India

    Vanthana Jeyasingh, Kumaresan Murugesan, Sudha Lakshminarayanan, Narayanan Selvapalam, Geetha Das & Lakshminarayanan Piramuthu

  2. Department of Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education , Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu, 626 126, India

    Vanthana Jeyasingh, Kumaresan Murugesan, Sudha Lakshminarayanan, Narayanan Selvapalam, Geetha Das & Lakshminarayanan Piramuthu

  3. Department of Chemistry, J.P. College of Arts & Science, Agarakattu, Ayikudi, Tamil Nadu, 627852, India

    Sudha Lakshminarayanan

  4. Department Chemistry, Department of Nanosciences and Technology, School of Science and Humanities, KITS, Coimbatore, Tamil Nadu, 641114, India

    I. V. Muthu Vijayan Enoch

Authors
  1. Vanthana Jeyasingh
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  2. Kumaresan Murugesan
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  3. Sudha Lakshminarayanan
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  4. Narayanan Selvapalam
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  5. Geetha Das
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  6. I. V. Muthu Vijayan Enoch
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  7. Lakshminarayanan Piramuthu
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Correspondence to Lakshminarayanan Piramuthu.

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Jeyasingh, V., Murugesan, K., Lakshminarayanan, S. et al. Most Efficient Tris(3-Aminopropyl) Amine Based Electron Deficient Tripodal Receptor for Azide. J Fluoresc 30, 291–300 (2020). https://doi.org/10.1007/s10895-020-02490-6

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