Synthesis and recognition properties of higher order tetrathiafulvalene (TTF) calix[n]pyrroles (n = 4–6)

Park, Jung Su; Bejger, Christopher; Larsen, Karina R.; Nielsen, Kent A.; Jana, Arundhati; Lynch, Vincent M.; Jeppesen, Jan O.; Kim, Dongho; Sessler, Jonathan L.

doi:10.1039/c2sc20636f

Cited by 28 publications

(23 citation statements)

References 31 publications

(11 reference statements)

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“…52 In this context, Sessler's group attached the TTF moiety at the bpositions of C4P to generate diverse TTF-C4Ps (29, 31, and 33), as shown in Schemes 3 and 4. [53][54][55][56][57]…”

Section: B-substituted Calix[4]pyrrolesmentioning

confidence: 99%

“…120 They designed and synthesized various TTF-C4Ps and other oligopyrrolic macrocycles. 55,[121][122][123][124][125][126] They utilized TTF-based C4P 31 (Scheme 4) and carried out anion binding studies with diverse anions such Table 1 Binding constants (using UV-Vis titrations) of 1, 56 and 57 for various anions…”

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confidence: 99%

“…1.8(AE0.09) Â 10 6 3.6(AE0.08) Â 10 4 50 TBACl À 1.02 Â 10 5 1.9(AE0.2) Â 10 6 1.1(AE0.05) Â 10 5 17 THACl À -2.5(AE0.2) Â 10 6 1.5(AE0.14) Â 10 5 as Br À , Cl À , CN À , NO 2 À , and AcO À by means of 1 H-NMR spectroscopy and isothermal titration calorimetry (ITC) techniques (Table 3). [52][53][54][55][56][57] Regarding the anion binding signicance of strapped C4Ps, researchers worldwide have employed various strapped C4Ps in the binding of diverse anions. In this context, Lee et al carried out anion binding studies of a host, 74 (Scheme 10), and conrmed that chloride anion rests inside the cavity.…”

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confidence: 99%

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New dimensions in calix[4]pyrrole: the land of opportunity in supramolecular chemistry

et al. 2019

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“…52 In this context, Sessler's group attached the TTF moiety at the bpositions of C4P to generate diverse TTF-C4Ps (29, 31, and 33), as shown in Schemes 3 and 4. [53][54][55][56][57]…”

Section: B-substituted Calix[4]pyrrolesmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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New dimensions in calix[4]pyrrole: the land of opportunity in supramolecular chemistry

et al. 2019

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“…[31,32,[94][95][96][97] In continuation of their work on tetrathiafulvalene-functionalized calix [4]pyrroles, Sessler and coworkers recently described the recognition properties of two higher order benzo-TTF-calix[n]pyrroles (n = 5 and 6) to- Reproduced with permission from ref. [98] All receptors bind anions with 1:1 stoichiometry with higher selectivity for chloride anions (K = 5.2 ϫ 10 5 , 1.30 ϫ 10 4 , and 5.30 ϫ 10 6 m -1 for 71, 72, and 73, respectively). ward anionic and neutral guests.…”

Section: β-Substituted Calix[4]pyrrolesmentioning

confidence: 99%

Recent Advancements in Calix[4]pyrrole‐Based Anion‐Receptor Chemistry

Saha

Lee

2015

Eur J Org Chem

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Calix[4]pyrroles and their congeners are conformationally flexible, nonplanar tetrapyrrolic macrocycles that can recognize anionic substrates. Although the mother calix[4]pyrrole was reported more than 100 years ago, anion recognition accompanied with conformational changes was first discovered in 1996. These compounds have shown preferential binding of halide anions such as fluoride and chloride as well as that of phosphate and carboxylate anions. Extensive efforts have been made to improve the affinity and selectivity. Continuous expansion of related research makes this easy‐to‐make macrocycle more promising. In this review, recent synthetic developments and the anion binding properties of newly developed calix[4]pyrroles are discussed and accomplishments to date are summarized. We hope that this review provides a seed for future developments in this area of chemistry.

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“…During the condensation of ketones with pyrrole, expanded calixpyrroles are also formed [6]. Among the calixpyrroles that have been explored previously, the calix [5]pyrroles are the most elusive from a synthetic point of view and, therefore, the least explored in terms of anion recognition and other applications [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Isotopic Labeling Study of the Formation of Calix[5]pyrroles Catalyzed by Bi(NO3)3

2013

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Abstract:One of the more elusive classes of macrocycles includes the calix[5]pyrroles, which can be obtained from pyrrole and acetone in the presence of low concentrations of Bi(NO 3 ) 3 -5H 2 O. An isotopic labeling experiment aided the proposal of a mechanism to explain the formation of calix [5]pyrrole at low acid concentrations and the exclusive formation of calix[4]pyrrole at high acid concentrations. We assume that the mechanism involves HNO 3 , which is released from the Bi salt.

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Synthesis and recognition properties of higher order tetrathiafulvalene (TTF) calix[n]pyrroles (n = 4–6)

Cited by 28 publications

References 31 publications

New dimensions in calix[4]pyrrole: the land of opportunity in supramolecular chemistry

New dimensions in calix[4]pyrrole: the land of opportunity in supramolecular chemistry

Recent Advancements in Calix[4]pyrrole‐Based Anion‐Receptor Chemistry

Isotopic Labeling Study of the Formation of Calix[5]pyrroles Catalyzed by Bi(NO3)3

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