Analytical applications of nano-baskets of calixpyrroles
- 504 Downloads
Calixpyrrole is one such class which holds a great promise in the fields of sensors and their unique behavior as sensors owes to its structural flexibility. Anion binding ability of calixpyrrole has been modified in a variety of ways. Introduction of electron releasing and electron withdrawing groups at the meso position or at β-pyrrolic positions leads to calixpyrrole with deep cavities and fixed walls which shows increased selectivity and modified binding effects. Strapping of calixpyrrole is another way to modify its structural behavior which is responsible for its binding behavior. Choice of strap could play a profound role not only in increasing the intrinsic anion binding affinity of calix pyrrole, but also in modulating the receptor anion stoichiometry, thereby modifying potentially the inherent anion binding selectivity. Calix[n]pyrroles with extended cavities have also been synthesized. Such as calixbipyrrole binds bromide substantially with high affinity than calixpyrrole. Calixpyrrole has also been used to produce anion sensors that can report the presence of anion by means of a color change. The medium effect on the complexation of calixpyrrole and anion has been investigated in various solvents. Calixpyrrole has also been used to increase the ionic conductivity of solid polymer electrolyte by anion complexation of the metal salt. Calixpyrrole has been used to obtain optical sensors using surface plasmon resonance technique. Composite films of cellulose acetate containing calixpyrrole has also been reported which has potential usage in packaging, storage and preservation. In nut shell, calixpyrrole can be modified in a variety of ways to form versatile sensors which can be used in variety of ways in various areas.
KeywordsNano-basket Calixpyrroles Ion recognition Hydrogen bonding Anion binding
This work was supported by Islamic Azad University (Shahreza branch) and Iran Nanotechnology Initiative Council.
- 5.D’Souza, F., Zandler, M.E., Tagliatesta, P., Ou, Z., Shao, J., Caemelbecke, E.V., Kadish, K.M.: Electronic, spectral and electrochemical properties of (TPPBrx)Zn where TPPBrx is the dianion of β-brominated-pyrrole tetraphenylporphyrin and x varies from 0 to 8. Inorg. Chem. 37, 4567–4572 (1998)CrossRefGoogle Scholar
- 6.Harrison, R.M.: Pollution: Causes, Effects and Control. RSC, London (1983)Google Scholar
- 8.Chelintzev, V.V., Tronov, B.V.: Production of calixpyrroles by the method of condensing acetone and pyrrole. J. Russ. Phys. Chem. Soc. 48, 105–106 (1916)Google Scholar
- 10.Chelintzev, V.V., Tronov, B.V.: Cyclehexyl phenyl ether and its isomerization to cyclohexylphenol. J. Russ. Phys. Chem. Soc. 48, 1197–1209 (1916)Google Scholar
- 22.Aydogan, A., Coady, D.J., Lynch, V.M., Akar, A., Marquez, M., Bielawski, C.W., Sessler, J.L.: Poly(methyl methacrylate)s with pendant calixpyrroles: polymeric extractants for halide anion salts. Chem. Commun. 1455–1457 (2008)Google Scholar
- 28.Anzenbacher Jr, P., Jurisikova, K., Lynch, V.M., Gale, P.A., Sessler, J.L.: Calixpyrroles containing deep cavities and fixed walls. Synthesis, structural studies and anion binding properties of the isomeric products derived from the condensation of p-hydroxyacetophenone and pyrrole. J. Am. Chem. Soc. 121, 11020–11021 (1999)CrossRefGoogle Scholar
- 31.Jayswal, K.P., Patela, J.R.: Design, synthesis, characterization and complexation studies of novel vanadophiles: calixpyrrole hydroxamic acids. Acta Chem. Solv. 55, 502–507 (2008)Google Scholar
- 34.Lui, K., Guo, Y., Xu, J., Shao, S.J., Jiang, S.X.: Synthesis of new 2,5-dimethyl pyrrole derivatives from acetonylacetone. Chinese Chem. Lett. 17, 387–390 (2006)Google Scholar
- 47.Floriani, C.: The porphyrinogen–porphyhrin relationship: the discovery of artificial porphyrins. Chem. Commun. 1257–1263 (1996)Google Scholar
- 56.Sessler, J.L., An, D., Cho, W.S., Lynch, V., Marquez, M.: Calixbipyrrole—a big, flexible, yet effective chloride-selective anion receptor. Chem. Commun. 540–542 (2005)Google Scholar