Abstract
The ternary complexes are formed by self-assembly through cooperative hydrogen bonding between p-SCX6-FL and M2+ through water molecule which is reinforced by columbic and electrostatic interactions. The binding efficiency of Cu2+ and Zn2+ is observed at a greater extent than Co2+ and Ni2+. Furthermore, the kinetic study of p-SCX6-FL-Cu2+ and Zn2+ reveals that the process of complexation is slower than the binary system (FL+p-SCX6).
Graphic abstract
Synopsis. Herein we report the systematic complexation study of ternary model i.e., p-SCX6-FL-M2+ by IR, NMR and UV-Visible and florescence technique.
Similar content being viewed by others
References
Müller-Dethlefs K and Hobza P 2000 Noncovalent Interactions: A Challenge for Experiment and Theory Chem. Rev. 100 143
Gokel G W, Atwood J L and Lehn J M 1996 Comprehensive supramolecular chemistry. Volume 1, Molecular recognition: receptors for cationic guests (New York: Pergamon)
Szejtli J, Atwood J L and Lehn J M 1996 Comprehensive Supramolecular Chemistry Vol. 3 (New York: Pergamon)
Márquez C, Hudgins R R and Nau W M 2004 Mechanism of host-guest complexation by cucurbituril J. Am. Chem. Soc. 126 5806
Nabeshima T, Saiki T, Iwabuchi J and A Shigehisa 2005 Stepwise and dramatic enhancement of anion recognition with a triple-site receptor based on the calix [4] arene framework using two different cationic effectors J. Am. Chem. Soc. 127 5507
Abd El-Rahman M K and Mahmoud A M 2015 A novel approach for spectrophotometric determination of succinylcholine in pharmaceutical formulation via host–guest complexation with water-soluble p-sulfonatocalixarene RSC Adv. 5 62469
Mokhtari B and Pourabdollah K 2012 Applications of calixarene nano-baskets in pharmacology J. Incl. Phenom. Macrocycl. Chem. 73 1
Schazmann B, O’malley S, Nolan K and Diamond D 2006 Development of a Calix [4] arene Sensor for Soft Metals Based on Nitrile Functionality Supramol. Chem. 18 515
Lee Y J, Park K D, Yeo H M, Ko S W, Ryu B J and Nam K C 2007 The molecular recognition of amines with calix[6]arene: conclusive X-ray and NMR evidence for endo and exo complex formation between calix[6]arene and amines Supramol. Chem. 19 167
Rurack K and Resch-Genger U 2002 Rigidization, preorientation and electronic decoupling—the ‘magic triangle’ for the design of highly efficient fluorescent sensors and switches Chem. Soc. Rev. 31 116
Spichiger-Keller U E 2008 Chemical sensors and biosensors for medical and biological applications (Weinheim: John Wiley & Sons)
Comstock M J and Comstock M J 1993 Fluorescent Chemosensors for Ion and Molecule Recognition, Copyright, Advisory Board, Foreword (Washington: ACS Publications)
Sharma K and Cragg P 2011 Calixarene based chemical sensors Chem. Sens. 1 1
Lynam C, Jennings K, Nolan K, Kane P, McKervey M A and Diamond D 2002 Tuning and enhancing enantioselective quenching of calixarene hosts by chiral guest amines Anal. Chem. 74 59
Helttunen K and Shahgaldian P 2010 Self-assembly of amphiphilic calixarenes and resorcinarenes in water New J. Chem. 34 2704
Natalino R, Varejão E V V, da Silva M J, Cardoso A L and Fernandes S A 2014 p-Sulfonic acid calix [n] arenes: the most active and water tolerant organocatalysts in esterification reactions Catal. Sci. Technol. 4 1369
Sliwa W and Girek T 2010 Calixarene complexes with metal ions J. Incl. Phenom. Macrocycl. Chem. 66 15
Zhang Y, Agbaria R A and Warner I M 1997 Complexation Studies of Water-soluble Calixarenes and Auramine O Dye Supramol. Chem. 8 309
Souchon V, Leray I and Valeur B 2006 Selective detection of cesium by a water-soluble fluorescent molecular sensor based on a calix [4] arene-bis (crown-6-ether) Chem. Commun. 4224
Aron A T 2015 Recognition- and Reactivity-Based Fluorescent Probes for Studying Transition Metal Signaling in Living Systems Acc. Chem. Res. 48 2434
Tang Y-Y, Chen S, Wang C-J, Zhu Z-X and Liu D-N 2018 Four coordination complexes based on two novel carboxylate-functionalized resorcin[4]arenes: Structures, fluorescence and sensing of nitrobenzene and dichromate anions Inorg. Chim. Acta 482 579
Han C, Zeng L, Li H and Xie G 2009 Colorimetric detection of pollutant aromatic amines isomers with p-sulfonatocalix[6]arene-modified gold nanoparticles Sens. Actuat. B: Chem. 137 704
Memon F N and Memon S 2012 Calixarenes: a versatile source for the recovery of Reactive Blue-19 dye from industrial wastewater Pak. J. Anal. Environ. Chem. 13 11
Gunupuru R, Maity D, Bhadu G R, Chakraborty A, Srivastava D N and Paul P 2014 Colorimetric detection of Cu2+ and Pb2+ ions using calix[4]arene functionalized gold nanoparticles J. Chem. Sci. 126 627
Bian Y, Li C and Li H 2010 para-Sulfonatocalix[6]arene-modified silver nanoparticles electrodeposited on glassy carbon electrode: preparation and electrochemical sensing of methyl parathion Talanta 81 1028
Chin S F, Makha M, Raston C L and Saunders M 2007 Magnetite ferrofluids stabilized by sulfonato-calixarenes Chem. Commun. 19 1948
Fang J, Saunders M, Guo Y, Lu G, Raston C L and Iyer K S 2010 Green light-emitting LaPO4: Ce3+:Tb3+ koosh nanoballs assembled by p-sulfonato-calix[6]arene coated superparamagnetic Fe3O4 Chem. Commun. 46 3074
Basilio N and García-Río L 2009 Sulfonated Calix [6] arene Host–Guest Complexes Induce Surfactant Self-Assembly Chem.–Eur. J. 15 9315-9
Liu Y, Bi Y, He W, Wang X, Liao W and Zhang H 2009 A copper/p-sulfonatocalix [6] arene/phenanthroline supramolecular compound with 1D [Cu2-calixarene] n coordination chains J. Mol. Struct. 919 235
Dsouza R N and Nau W M 2008 Triple Molecular Recognition as a Directing Element in the Formation of Host-Guest Complexes with p-Sulfonatocalix [4] arene and β-Cyclodextrin J. Org. Chem. 73 5305
Bakirci H, Koner A L, Dickman M H, Kortz U and Nau W M 2006 Dynamically Self-Assembling Metalloenzyme Models Based on Calixarenes Angew. Chem. Int. Edit. 45 7400
Li Y, Wu J, Jin X, Wang J, Han S, Wu W, Xu J, Liu W, Yaoa X and Tang Y 2014 A bimodal multianalyte simple molecule chemosensor for Mg2+, Zn2+, and Co2+ Dalton Trans. 43 1881
Izzet G, Douziech B, Prangé T, Tomas A, Jabin I, Le Mest Y and Reinaud O 2005 Calix[6]tren and copper(II): A third generation of funnel complexes on the way to redox calix-zymes Proc. Nat. Acad. Sci. U. S. A. 102 6831
Lakowicz J R 2013 Principles of Fluorescence Spectroscopy (US: Springer Science & Business Media)
Sliwa W and Girek T 2010 Calixarene complexes with metal ions J. Incl. Phenom. Macrocycl. Chem. 66 15
Thomas A, Nair P V and Thomas K G 2014 InP quantum dots: an environmentally friendly material with resonance energy transfer requisites J. Phys. Chem. C 118 3838
Patil S V, Athare S V, Jagtap A, Kodam K M, Gejji S P and Malkhede D D 2016 Encapsulation of rhodamine-6G within p-sulfonatocalix[n]arenes: NMR, photophysical behaviour and biological activities RSC Adv. 6 110206
Thorave R G, Lande D N, Athare S V, Gejji S P, Gonnade R G and Malkhede D D 2017 X-ray structure, spectral characteristics, thermal and redox behavior of quinoline encapsulated in sulfonatocalix [4] arene J. Mol. Liq. 246 187
Hilmersson G and Davidsson O 1995 A Multinuclear NMR Study of a Chiral Lithium Amide with an Intramolecular Chelating Methoxy Group in Coordinating Solvents at the Slow Ligand Exchange Limit J. Org. Chem. 60 7660
Acknowledgement
We thank the University Grants Commission, New Delhi for financial support. We also thank Central Instrumentation Facility, Savitribai Phule Pune University for NMR analysis.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Gawhale, S., Rathod, N., Patil, S. et al. The investigation of cooperative binding between p-sulfonatocalix[6]arene and fluorescein with transition metal ions by spectrometrically. J Chem Sci 132, 16 (2020). https://doi.org/10.1007/s12039-019-1717-3
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1007/s12039-019-1717-3