Templated assembly of a molecular capsule

Crossley, M. J.; Reek, Joost N. H.; Schenning, Albert P. H. J.; Bosman, Anton W.; Meijer, E. W.

doi:10.1039/a707748c

Cited by 74 publications

(21 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The three major products from the crude reaction mixture could be isolated by chromatography over silica gel and separation was best achieved as their dizinc(II) chelates. The homocoupled dizinc(II) Trçgers base bis-porphyrin [16] was isolated in 52 % yield and extended dizinc(II) Trçgers base bisquinoxalinoporphyrin [14,17] was obtained in 48 % yield. Once isolated, dizinc(II) asymmetric bis-porphyrin 3 was demetallated by treatment with hydrochloric acid to yield the freebase asymmetric bis-porphyrin 4 in 14 % overall yield from 2.…”

Section: Resultsmentioning

confidence: 99%

“…The second major band was collected to yield 3 (37 mg) as a purple residue. This material was not analytically pure, but identification by 1 The third major fraction was collected to yield dizinc(II) extended Trç-gers base bis-porphyrin [14,17] (53 mg, 48 %) with identical spectral properties to those previously reported. Compound 3 (37 mg) was dissolved in dichloromethane (20 mL) and shaken with hydrochloric acid (32 % w/v, 10 mL) for 5 min.…”

Section: Synthesis Ofmentioning

confidence: 99%

See 1 more Smart Citation

Regioselective Reactivity of an Asymmetric Tetravalent Di[dihydroxotin(IV)] Bis‐Porphyrin Host Driven by Hydrogen‐Bond Templation

Brotherhood¹,

Luck²,

Blake³

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

Local molecular environment effects on the rates of ligand exchange at an asymmetric di[dihydroxotin(IV)] bis-porphyrin 5 are examined. The host 5 possesses four non-equivalent tin(IV)-ligand binding sites that are distinguished by their position relative to a shallow cavity, by the steric environment at each binding site and by electronic-structure differences between the constituent porphyrin and quinoxalinoporphyrin macrocycles. These design features of the asymmetric host are confirmed by X-ray crystal structure analysis. Binding experiments with monodentate carboxylic acids and bidentate dicarboxylic acids show significant differences in the rate of ligand exchange at each of the four tin(IV) binding sites. For monodentate carboxylic acids, binding preferentially occurs at the exterior porphyrin site. Further addition of carboxylic acid results in sequential binding at the quinoxalinoporphyrin sites and lastly at the interior site on the porphyrin, with high regioselectivity. These selective binding outcomes are immediately apparent by NMR spectroscopy. A series of 2D NMR spectroscopy experiments allowed identification of the preferred binding sites at the host. This positively identifies that steric hindrance and electron-withdrawing functionality on the porphyrin macrocycle impede ligand exchange. However, these effects are overcome by dicarboxylic acid guests, which form ditopic hydrogen-bond interactions between the intracavity hydroxo ligands in the initial stage of ligand exchange, leading to regioselective binding between the tin(IV) sites within the cavity. It is envisaged that the factors identified herein that define regioselective ligand exchange at host 5 will find wider application in supramolecular systems incorporating tin(IV) porphyrins.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Ofmentioning

confidence: 99%

Regioselective Reactivity of an Asymmetric Tetravalent Di[dihydroxotin(IV)] Bis‐Porphyrin Host Driven by Hydrogen‐Bond Templation

Brotherhood¹,

Luck²,

Blake³

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…These series of bisporphyrino‐TB analogues with inserted metal ions exhibited strong affinities with different selectivities towards diamine guests such as α,ω‐diaminoalkanes of different lengths,95a as well as towards histidine and lysine esters 95b. TB analogue 97 (Figure 22), in addition to binding simple diaminoalkanes, encapsulated a tetramine dendrimer, forming a spherical cage 95c. Specifically, in a recent report based on similar structures, the Crossley group demonstrated ditopic binding of an α,ω‐dicarboxylic acid in the cavity when Sn(OH) 2 was coordinated to the porphyrin rings 96…”

Section: Applications Of Tröger's Base Analoguesmentioning

confidence: 99%

Prevention of postoperative adhesion formation by individual and combined administration of 4 per cent icodextrin and dimetindene maleate (Br J Surg 2009; 96: 1476–1483)

Watkins¹

2010

British Journal of Surgery

View full text Add to dashboard Cite

show abstract

“…[16 -25] As a matter of fact, recent efforts on the design and construction of novel porphyrin arrays have highly increased. [21 -25] As a result, a variety of covalently linked porphyrin arrays have been developed, which include linear, [26,27] cyclic, [28] dendritic, [29] stacked, [30] starburst, [31] bandanna, [32] fused, [33] and other fascinating three-dimensional arrangements. [34,35] Feature Article: Our synthetic attempts for the preparation oligo-and polyporphyrin arrays were reviewed in comparison with recent accomplishment in the related field.…”

Section: Introductionmentioning

confidence: 99%