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Functionalized Calixpyrroles: Building Blocks for Self-Assembly

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Calixarenes and Beyond

Abstract

This chapter covers advances in the development of anion and ion pair recognition systems based on calix[4]pyrrole. The intention of this manuscript is to provide of an overview of promising systems for the sensing of relevant analytes, such as the toxic fluoride anion, phosphate anions, as well as the extraction and transport of anionic species and ion pairs including cesium halide and sulfate salts. It is divided into seven sections. The first section describes the synthetic methods employed to functionalized calix[4]pyrrole. The second section focuses on functionalized calix[4]pyrroles that display enhanced anion binding properties compared to the non-functionalized parent system, octamethylcalix[4]pyrrole. The use of functionalized calix[4]pyrroles containing a fluorescent group or functionalized calix[4]pyrroles as building blocks for the preparation of stimulus-responsive materials is discussed in Sect. 12.3. Receptors that are able to recognize and selectively extract ionic species from aqueous media into organic environments are the topic of Sect. 12.4. Anion and ion pair receptors based on calix[4]pyrroles that are designed to achieve the transmembrane transport of ions are the focus of the fifth section. Finally, the last section will summarize work devoted on calix[4]pyrrole systems capable of forming higher order supramolecular aggregates and capsules, as well as studies of their response to external stimuli. Potential applications, including the possible removal of deleterious anions and the eventual development of therapeutics that function via the transport of anions across cell membranes, are discussed.

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Acknowledgement

Support for this work was provided by the Office of Basic Energy Sciences, U.S. Department of Energy (DOE) (grant number DE-FG02-01ER15186 to J.L.S.) and the National Science Foundation (grant CHE CHE-1402004 to J.L.S.).

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Authors and Affiliations

  1. Department of Chemistry, The University of Texas at Austin, 105 E 24th St. Stop A5300, Austin, TX, 78712-1224, USA

    Gabriela I. Vargas-Zúñiga & Jonathan L. Sessler

  2. Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230, Odense M, Denmark

    Steffen Bähring

Authors
  1. Gabriela I. Vargas-Zúñiga
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  2. Jonathan L. Sessler
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  3. Steffen Bähring
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Correspondence to Jonathan L. Sessler .

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Editors and Affiliations

  1. Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, Fisciano, Salerno, Italy

    Placido Neri

  2. Department of Chemistry, The University of Texas, Austin, Texas, USA

    Jonathan L. Sessler

  3. Department of Chemistry, Tsinghua University, Beijing, China

    Mei-Xiang Wang

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Vargas-Zúñiga, G.I., Sessler, J.L., Bähring, S. (2016). Functionalized Calixpyrroles: Building Blocks for Self-Assembly. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_12

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