A modular approach to potential synthetic receptors with large surfaces based on crown[n]cavitands

European Journal of Organic Chemistry

Volumn , Issue 8, 1998, Pages 1597-1607

  Higler, Irene ^a   Boerrigter, Harold ^b   Verboom, Willem ^a   Kooijman, Huub ^c   Spek, Anthony L ^c   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b TNO   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Building blocks; Calix 4 arenes; Cavitands; Crown compounds; Modular approach

Indexed keywords

EID: 0001778891     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199808)1998:8<1597::AID-EJOC1597>3.0.CO;2-1     Document Type: Article

References (40)

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21. Although the combination of calix[4]arenes and crown ether elements are referred to as calix[4]crowns, the combinations of resorcin[4]arenes and crown ether elements will be referred to as crown[n]cavitands to make it possible to distinguish between 1,2-crown[n]cavitands 1-3 and 1,3-crown[n]cavitands.
22. The official name for the unsubstituted methylene-bridged cavitand with R groups at the para positions and with four alkyl chains at the bottom is 7,11,15,28-tetra"R"-1,21,23,25-tetra-"alkyl"-2,20:3,19- dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5′,4′-i′] benzo[1,2-d:5,4-d′]bis[1,3]benzodioxocin. For simplicity reasons we have given each of the resorcin[4]arene aromatic rings a number (1-4); therefore, we call a 7,11-difunctionalized cavitand a 1,2-difunctionalized cavitand.
23. In most calix[n]crowns, the crown ether unit is introduced after dialkylation of the calix[4]arene at opposite rings. In those cases, the crown ether unit will connect two hydroxy groups at opposite rings.
24. 2v symmetry.
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27. Two tetrahydroxycavitands were, among others, connected via four butyl spacers or via four meta-xylene spacers; for an example see: R. C. Helgeson, K. Paek, C. B. Knobler, E. F. Maverick, D. J. Cram, J. Am. Chem. Soc. 1996, 118, 5590-5604.
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33. Addition of prednisolone-21-acetate, quinidine, or β-D-ribofuranose tetraacetate to a solution of 15e in chloroform did not give any significant shift of host or guest signals. Extraction experiments with dipeptides glycyl-leucine and glycyl-tyrosine, tripeptide glycyl-glycyl-leucine, and tetrapeptide glycyl-glycyl-glycyl-glycine showed that 1:1 endo 15e does not complex these peptides. Also solid-liquid (chloroform) and liquid-liquid (water and chloroform) extraction experiments with 5-amino-n-valeric acid, 4-aminophenyl acetic acid, and 4-(aminomethyl)benzoic acid did not give any indications for complexation by 1:1 endo 15e.
34. 1H-NMR spectra with a superscript "n" or "x" is shown (as far as known) indicating whether the signal belongs to the endo or the exo isomer, respectively. The number of hydrogen atoms is assigned as if only one isomer is present.
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40. The disorder in one of the pentyl moieties has been excluded for clarity reasons.