Supramolecular Liquid Crystals Based on Cyclo[8]pyrrole

Stępień, Marcin; Donnio, Bertrand; Sessler, Jonathan L.

doi:10.1002/anie.200603893

Cited by 119 publications

(47 citation statements)

References 46 publications

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“…These results are worse in the case of the dianions and still more in the case of the PO 4 3-that is the only calculated trianion. However, a linear correlation can be derived from Table 1 Then, we calculated the twelve complexes (Table 2) formed between 2 and 3 and the mentioned six anions.…”

Section: Resultsmentioning

confidence: 85%

“…However, a linear correlation can be derived from Table 1 Then, we calculated the twelve complexes (Table 2) formed between 2 and 3 and the mentioned six anions. The strength of the interaction in gas phase is clearly dominated by the electrostatic term and thus the stronger interaction corresponds to the complex of the dication 2 with the trianion PO 4 3-. Thus, the representation of the interaction energy vs. the sum of absolute value of the charges in the isolated monomers that constitutes the complex (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…For instance, including water solvation, the dication 2 presents an interaction with the sulfate dianion and the nitrate monoanion of -134.9 and -22.1 kJ mol -1 , respectively. The first interesting result is the small value observed in the solvation of the complexes formed by 2 with the dianions (SO 4 2-and CO 3 2-) which results in a neutral complex. The solvation energy of the complexes of 3 is somehow related to those of the isolated anions but with smaller values since the polar moieties of them are not accessible to the solvent.…”

Section: Resultsmentioning

confidence: 99%

“…In 2007, Sessler, Moyer and coworkers reported the synthesis and complexation properties of octamethyloctaundecylcyclo [8]pyrrole dication 1 as a promising sulfate anion extractant [1] (the importance of this paper was highlighted in Chemical & Engineering News [2]; for preceding Sessler papers on this compound, see [3,4]). The main conclusion was that 1 is able to extract the sulfate anion, SO 4 2-, in the presence of a large excess of the nitrate anion, NO 3 -, from a water solution overcoming the Hofmeister bias [5,6].…”

Section: Introductionmentioning

confidence: 99%

“…The main conclusion was that 1 is able to extract the sulfate anion, SO 4 2-, in the presence of a large excess of the nitrate anion, NO 3 -, from a water solution overcoming the Hofmeister bias [5,6].…”

Section: Introductionmentioning

confidence: 99%

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A theoretical study of the neutral and the double-charged cation of cyclo[8]pyrrole and its interaction with inorganic anions

2009

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A theoretical study of the neutral and the double-charged cation of cyclo[8]pyrrole and its interaction with inorganic anions

2009

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Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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Anion Receptors Containing Heterocyclic Rings

Gale¹,

Haynes²

2012

Supramolecular Chemistry

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Heterocyclic groups can play key roles as hydrogen bond donors and charged components in a wide range of anion receptors. This chapter reviews the roles the heterocycles play in anion recognition, covering pyrrole‐based systems (both macrocyclic and acyclic, including synthetic systems and natural products such as prodigiosin), indole‐based receptors, and foldamers‐ and charged‐imidazolium‐based hosts. The chemistry of pyridine‐ and quinoline‐based receptors, including metal‐templated systems that employ transition metals to assemble simple organic components, and the role of bipyridinium in anion complexation and sensing are also reviewed. Finally, the chemistry of 1,2,3‐triazoles as components of hosts that use CH· · ·anion hydrogen bonds to complex anionic guests is examined.

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Supramolecular Liquid Crystals Based on Cyclo[8]pyrrole

Cited by 119 publications

References 46 publications

A theoretical study of the neutral and the double-charged cation of cyclo[8]pyrrole and its interaction with inorganic anions

A theoretical study of the neutral and the double-charged cation of cyclo[8]pyrrole and its interaction with inorganic anions

Porphyrins and Expanded Porphyrins as Receptors

Anion Receptors Containing Heterocyclic Rings

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