Exploiting the 1,2,3‐Triazolium Motif in Anion‐Templated Formation of a Bromide‐Selective Rotaxane Host Assembly

Mullen, Kathleen M.; Mercurio, James M.; Serpell, Christopher J.; Beer, Paul D.

doi:10.1002/anie.200901313

Cited by 154 publications

(82 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In particular, the click-chemistry generated 1,2,3-triazole has recently made a very strong impression on the supramolecular Fig. 19 Chloride-templated self-assembly of pseudorotaxane 35 þ l Cl À [87] utilizing the affinity of both wheel 34 and triazolium based axle 33…”

Section: Discussionmentioning

confidence: 99%

“…Beer has also demonstrated the ability of this 2+ [83] was designed with dialkylammonium and triazolium binding "stations." Upon deprotonation, the crown shuttled to the strong triazolium binding station methodology in a rotaxane synthesis [87] utilizing ring closing metathesis around the triazolium axle, in which the rotaxane has been shown to bind selectively to bromide.…”

Section: Triazolium Ch Lll X à Interactions In Anion Templationmentioning

confidence: 99%

“…Until recently, the ability of a CH hydrogen bond donor to act as a means of accessing anion-templated interlocked structures has gone unexplored. Beer has developed [87] a triazolium based axle 33 + (Fig. 19) which has shown a very high affinity for Cl À and Br À in acetone-d 6 .…”

Section: Triazolium Ch Lll X à Interactions In Anion Templationmentioning

confidence: 99%

See 2 more Smart Citations

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

McDonald

Hua

Flood

2010

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

As the field of anion supramolecular chemistry continues to grow in its sophistication and understanding of the noncovalent interactions used to effectively bind anions, there exists new theoretical and experimental evidence for a necessary reexamination of the way in which the field views hydrogen bond donors. The heteroatom based hydrogen-bond donors (e.g., NH and OH) are well-known to provide strong stabilization to negatively charged species. However, new findings point to the untapped stabilization energy that lay dormant in extrinsically-activated CH hydrogen bonds. Computational studies showed that an activated aliphatic or aromatic CH can provide an amount of anion stabilization in the gas phase approaching that of conventional NH based donors. Discovery of the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition to provide 1,2,3-triazoles and the ability to readily "click" this functionality into anion receptors has allowed extensive experimental investigation of the ideas posed by these calculations. This chapter will focus on the evolution of the CH hydrogen bond from being viewed as a weak, secondary interaction to now being utilized as a powerful source of anion stabilization in macrocyclic and oligomeric receptors. In addition, the application of the anion binding power of the 1,2,3-triazole towards the preparation of mechanically interlocked structures will also be discussed.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Triazolium Ch Lll X à Interactions In Anion Templationmentioning

confidence: 99%

See 1 more Smart Citation

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

McDonald

Hua

Flood

2010

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

show abstract

“…The assembly of 18, iodotriazolium 19a + , and Br À was trapped by ring-closing metathesis, generating 20a + · Br À in 15% yield. An analogous chloride-templated protocol was used to access the unsubstituted triazolium-based rotaxane 20b + · Cl À [57]. After the templating ions were exchanged for non-coordinating PF 6 À , the halide affinities of the rotaxanes were studied.…”

Section: Anion Recognition Through Combinations Of Halogen and Hydrogmentioning

confidence: 99%

Anion Recognition in Solution via Halogen Bonding

Taylor

2014

Topics in Current Chemistry

View full text Add to dashboard Cite

An overview of the interactions between anions and electron-deficient, covalently bound halogens is presented. It might be anticipated that species such as halides and oxoanions would be good acceptors of halogen bonds because of their relatively high charge densities and nucleophilicities. The stabilities of the trihalide anions X3 (-) provide a clear indication that this is indeed the case. The thermodynamics of formation of the trihalides, and of analogous complexes between anions and monodentate haloorganics in organic solvent, are discussed in detail. Although the incorporation of multiple interacting groups to achieve high guest affinity has been a key principle of supramolecular chemistry for decades, it is only recently that multidentate halogen bond donors capable of anion recognition have been reported. This contribution highlights the range of architectures that have been employed as the basis for multidentate halogen bond donor design. Examples of selective and high-affinity anion recognition through halogen bonding, including implementations in polar, protic media, are discussed.

show abstract

“…7a,10 Subsequent regioselective methylation 11 with methyl triflate at the nitrogen atoms closest to the benzene core yielded the respective dicationic XB donors as triflate salts. We note that 1,3-I R-MeBn /OTf represents, to the best of our knowledge, the first synthetically obtained chiral XB donor.…”

mentioning

confidence: 99%

5-Iodo-1,2,3-triazolium-based multidentate halogen-bond donors as activating reagents

et al. 2012

View full text Add to dashboard Cite

show abstract

Exploiting the 1,2,3‐Triazolium Motif in Anion‐Templated Formation of a Bromide‐Selective Rotaxane Host Assembly

Abstract: Bromide is best: The first [2]rotaxane incorporating the triazolium anion-binding motif is prepared using bromide anion templation. Preliminary anion-binding investigations reveal that the rotaxane exhibits the rare selectivity preference for bromide over chloride ions.

Cited by 154 publications

References 39 publications

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

Anion Recognition in Solution via Halogen Bonding

5-Iodo-1,2,3-triazolium-based multidentate halogen-bond donors as activating reagents

Contact Info

Product

Resources

About