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Calixarenes: Versatile Molecules As Molecular Sensors for Ion Recognition Study

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Calixarenes: Versatile Molecules As Molecular Sensors for Ion Recognition Study J. Chem. Sci. Vol. 124, No. 6, November 2012, pp. 1287–1299. c Indian Academy of Sciences. Calixarenes: Versatile molecules as molecular sensors for ion recognition study SUBRATA PATRA, DEBDEEP MAITY, RAVI GUNUPURU, PRAGATI AGNIHOTRI and PARIMAL PAUL∗ Analytical Science Division, Central Salt and Marine Chemicals Research Institute (constituents of CSIR, New Delhi), G B Marg, Bhavnagar 364 002, India e-mail: [email protected] Abstract. This article presents a brief account on designing of calixarene-based molecular sensor for recog- nition of various metal ions and anions and also different analytical techniques to monitor the recognition event. This review focuses only on calix[4]arene derivatives, in which mainly the lower rim is modified incorporat- ing either crown moiety to make calix–crown hybrid ionophore to encapsulate metal ions or some fluoregenic inorganic and organic moieties to use it as signalling unit. In order to investigate effect of conformation of the calixarene unit and steric crowding on ion selectivity, designing of these molecules have been made using both the cone and 1,3-alternate conformations of the calixarene unit and also incorporating bulky ter-butyl group in few cases to impose controlled steric crowding. Among various ions, here focuses are mainly on biologically and commercially important alkali metal ion such as K+, toxic metal ions such as Hg2+,Pb2+,Cd2+, impor- tant transition metal ion such as Cu2+ and toxic anion like F−. The techniques used to monitor the recognition event and also to determine binding constants with strongly interacting ions are fluorescence, UV-vis and 1H NMR spectroscopy. Most of the ionophores reported in this review have been characterized crystallographi- cally, however no structural information (except one case) are incorporated in this article, as it will occupy space without significant enhancement of chemistry part. Different factors such as size of the ionophore cavity, size of metal ion, coordination sites/donor atoms, steric crowding and solvents, which determine selectivity have been discussed. Response of ion recognition process to different analytical techniques is another interesting factor discussed in this article. Keywords. Molecular sensor; calixarene; ion recognition; fluoroionophores; supramolecular chemistry. 1. Introduction Ion-selectivity of the calixarenes are controlled by different factors such as conformation of the calix Design and synthesis of functional molecules that could moiety (2), binding sites, size of the ionophore cavity, serve as molecular devices for sensing of specific ion is steric crowding, solvent used and also response of the an area of intense activity in current research. 1 Different recognition event to different analytical techniques. We types of organic molecules have been used as ionophore have been working in this area for last few years and to design molecular sensor, however, macrocyclic li- have synthesized series of new molecular sensors incor- gands are excellent choices for this purpose because porating calix[4]arene derivatives as ionophore. 5–10 The of their remarkable selectivity towards various metal ion-recognition property of all these molecules has been ions. In this regard, calixarenes, which are macrocyclic investigated with a wide range of cations and anions and oligomers made up of phenol units linked by methy- the recognition event was monitored by various spectro- lene bridge are found to be very attractive because scopic techniques. On the basis of our study, we report of their ability to bind variety of ions. 1,2 In the cal- here a brief account of the various aspects of design and ixarene family, calix[4]arenes are most popular because ion-selectivity of calixarene derivatives as molecular of their rigid structures, which make them ideal candi- sensor. dates for the complexation with metal ions (1). 2–4 Both the upper and lower rims of the calixarene can be modi- fied depending on the requirement and these modified 2. Design of receptors for selective recognition calixarenes provide a highly preorganized architecture of alkali and alkaline earth metal ions for the assembling of converging binding sites. For the recognition of alkali and alkaline earth metal ions, a new class of hybrid molecule has been developed ∗For correspondence incorporating crown ethers into calix[4]arene. 5,6,8,11 The 1287 1288 Subrata Patra et al. Table 1. Selectivity ratio with respect to potassium ion in the extract and + + association constant (Ka) for Na and K . Selectivity Association a ratio constants (Ka) Compound K+/Na+ K+/Mg2+ K+/Ca2+ Na+ K+ 3a 1.7 12.2 6.0 1.06 × 104 1.82 × 106 3b 1.2 16.5 4.9 8.70 × 104 3.25 × 105 3c 0.3 – 1.4 5.17 × 104 – 3d 2.7 – – 3.12 × 106 7.20 × 107 3e 1.5 60.9 16.9 5.96 × 106 5.80 × 107 a The ratio is calculated by [% of K+ in the extract][% of Mn+ in the original solution]/[% of Mn+ in the extract][% of K+ in the original solution]. ion selectivity of this class of compounds is mainly X-ray structure determination of the ionophores and depend on the conformation of the calixarene platform, their Na+ and K+ complexes provides an insight about the size of the crown ether ring, the substituents at the structure–selectivity correlation and the effect of the upper rim of the calixarene and the appended intramolecular interactions on complexation. Crystal functional groups at the two sides of the crown ring. structures of the metal complexes revealed that the K+ Among various conformations of the calixarene, 1,3- ion fits well in the cavity making interaction with all the alternate conformers have been studied more exten- eight oxygen donor atoms forming strong complexes sively as complexing agent for alkali-metal ions. 12 whereas Na+ ion is coordinated with six oxygen atoms Regarding size of the ionophore, the cavity contain- leaving two uncoordinated, suggesting that the size of ing crown-5 and crown-6 are found more suitable the Na+ does not fit well in the cavity to make inter- for complexation, specially for Na+ and K+. 5,6,12 As action with all the oxygen donors (figure 2). Crystal part of our effort to develop suitable molecules for structures also show that in all cases one of the two selective extraction of K+ from natural sources such appended substituents coordinates with the metal ion. as brine and bittern, which mainly contain Na+,K+, The finding from crystal structures is therefore, consis- Ca2+ and Mg2+, a series of receptors containing p-tert- tent to the order of selectivity and association constants butylcalix[4]arene-crown-5 were designed and synthe- determined experimentally. The size matching factor sized. 5 To impose controlled steric crowding and also and intra/intermolecular interaction are, therefore play to investigate the effect of substituents at side arms an important role to determine selectivity. (like ‘lariat’ crown ether), a number of substituents (H, COCH3,CH2CO2C2H5 and CH2CO2H) appended at the opposite phenolic oxygen atoms of the crown moiety are incorporated (3a–3e). Selectivity of these ionophores towards Na+,K+,Mg2+ and Ca2+ were evaluated with aqueous solution containing equimolar mixture of these ions (table 1). The concentration of metal ion in the extract (organic phase) has been esti- mated by ion chromatographic assay. Among these ions, K+ showed highest selectivity in all cases, except in one case where access to the metal ion is blocked offasa resultofstrongC–H...Ointeractionsamong the pendant COCH3 substituents and crown moiety (figure 1). All the ionophores show poor selectivity 2+ 2+ towards Mg and Ca . Association constants (Ka) for + + Figure 1. Capped stick model of compound 3c, showing the binding of Na and K to these ionophores have C–H....Ointeractions(dottedline)involvingmethylhydro- been determined spectrophotometrically and it follows gen atoms of COCH3 groups and oxygen atoms (O6 and O8) the same order as selectivity (table 1). Single crystal of the crown moiety. Calixarenes as versatile molecular sensors 1289 Figure 2. Crystal structures of the receptors 3d (a) and its Na+ (b) and K+ (c) complexes. 3. Effect of steric crowding on ion selectivity whereas ionophore of same ring size as 4a and with for calix–crown hybrid ionophores tert-butyl at upper rim (4c) exhibits selectivity towards only Na+ and ionophore with three tosyl substituents A number of calix[4]arene-azacrown with variation in at the lower rim (4d) exhibited no complexation with ring size and bulky substituents at the upper and lower any metal ion. The steric crowding has nicely con- rims were synthesized to investigate the effect of steric trolled the selectivity. For the determination of binding crowding towards ion selectivity. 8 The substituent, constants, NMR titrations were carried out with the p-toluene sulphonamide is attached with the nitrogen strongly interacting metal ions. Interestingly, in a few atom(s) of the crown moiety and tert-butyl/hydrogen cases (K+ for 4a, and Na+ for 4c), upon addition of is incorporated in the upper rim (4a–4d). All of these increasing concentration of metal ions new peaks were compounds were characterized crystallographically. observed with gradual disappearance of the original Interaction of these ionophores with a large number of signals whereas in other cases, gradual shift of certain + + + + + + + + metal ions (Li ,Na ,K ,Rb ,Cs ,Mg2 ,Ca2 ,Sr2 , signals were noted with the addition of metal ions. This + + + + + Ba2 ,Zn2 ,Cd2 ,Hg2 and Pb2 ) has been investi- is because of the compatibility of the metal ion in the gated by NMR study. The ionophore without tert-butyl cavity, if metal ion fits appropriately then new peak + at upper rim (4a) showed selectivity towards both Na appears for the complex and if the metal ion does not + and K , ionophore with larger crown ring and without fit properly, then bond dissociation and association take tert-butyl at upper rim (4b) exhibited complexation place simultaneously resulting in gradual change in + + + + with K ,Rb ,Ba2 and weak interaction with Na , chemical shifts of certain signals.
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