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Issue 41, 2015
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α,ω-Alkanediyldiammonium dications sealed within calix[5]arene capsules with a hydrophobic bayonet-mount fastening

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Abstract

A combined XRD and 1H NMR study revealed that two molecules of tetrakis-(tert-butyloxycarbonylmethoxy)-calix[5]arene carboxylic acid are able to efficiently encapsulate α,ω-diaminoalkanes of suitable length as a result of proton-transfer-mediated recognition. In the case of 1,10-diaminodecane and 1,11-diaminoundecane, rim-to-rim attractive van der Waals interactions drive the formation of capsular complexes with a packing coefficient close to 70%. The two calixarene bowls in these capsules are seen in an eclipsed conformation. On the other hand, when the longer 1,12-diaminododecane guest is used, a quasi-capsular complex is formed in which the capsule seal is lost and the two calixarenes are arranged in a staggered conformation as a result of a reciprocal rotation of the two facing macrocyclic cavities. A comparison with similar capsular complexes confirms that a hydrophobic ‘bayonet-mount’ fastening is mandatory for the encapsulation of suitably sized guests.

Graphical abstract: α,ω-Alkanediyldiammonium dications sealed within calix[5]arene capsules with a hydrophobic bayonet-mount fastening

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Publication details

The article was received on 04 Aug 2015, accepted on 15 Sep 2015 and first published on 15 Sep 2015


Article type: Paper
DOI: 10.1039/C5CE01558H
CrystEngComm, 2015,17, 7915-7921

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    α,ω-Alkanediyldiammonium dications sealed within calix[5]arene capsules with a hydrophobic bayonet-mount fastening

    G. Brancatelli, G. Gattuso, S. Geremia, N. Manganaro, A. Notti, S. Pappalardo, M. F. Parisi and I. Pisagatti, CrystEngComm, 2015, 17, 7915
    DOI: 10.1039/C5CE01558H

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