Hydrogen bonding elements, π - hole functional moieties and C3v tripodal scaffold controlled turn-on cyanide and turn-off azide selective receptors

Kumaresan Murugesan; Vanthana Jeyasingh; Sudha Lakshminarayanan; Lakshminarayanan Piramuthu; Selvapalam Narayanan; Geetha Das

doi:10.1016/j.saa.2019.117285

Hydrogen bonding elements, π - hole functional moieties and C₃v tripodal scaffold controlled turn-on cyanide and turn-off azide selective receptors

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Dec 5:223:117285. doi: 10.1016/j.saa.2019.117285. Epub 2019 Jun 19.

Authors

Kumaresan Murugesan¹, Vanthana Jeyasingh¹, Sudha Lakshminarayanan², Lakshminarayanan Piramuthu³, Selvapalam Narayanan¹, Geetha Das¹

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; Department of Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu 626 126, India.
² International Research Centre, Centre for Supramolecular Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu 626 126, India; Department of Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu 626 126, India; Department of Chemistry, J.P. College of Arts & Science, Agarakattu, Ayikudi, Tamil Nadu 627852, India.
³ International Research Centre, Centre for Supramolecular Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu 626 126, India; Department of Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu 626 126, India. Electronic address: [email protected].

PMID: 31299616
DOI: 10.1016/j.saa.2019.117285

Abstract

Here in, we are reporting electron deficient amide and sulfonamide based tripodal receptors L, L¹, L² and L³. Systematic studies show a strong selectivity towards cyanide and azide anions. Detailed UV-Visible and fluorescent spectrometric investigation shows the amide based tripodal receptors L and L³ acts as a colorimetric and turn-on fluorescent chemo-sensor for cyanide, and the sulfonamide based tripodal receptors L¹ and L² acts as a colorimetric and turn-off fluorescent chemo-sensor for azide. At the end we have successfully prepared tripodal receptors for a particular anion with judicious choice of recognition elements such as hydrogen bonding amide/sulfonamide moiety, electron deficient pentafluorophenyl functionality for anion-π interaction and the well defined C₃v symmetric tripodal backbone for perfect recognition.

Keywords: Colorimetric sensor; Cyanide sensor; Tripodal receptors.