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

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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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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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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).

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