ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The dendritic cyclophanes (dendrophanes )1-3 containing a [6.1.6.1]paracyclophane as the initiator core embedded in dendritic poly(ether-amide) shells of first (1), second (2), and third (3) generation were prepared and characterized. The X-ray crystal-structure analyses of esters 7 and 4, derivatives of cyclophane core 9 and first-generation dendrophane 1, respectively, displayed open cavity binding sites suitable for the inclusion complexation of aromatic substrates. With their carboxylate surface groups, dendrophanes 1-3 were readily soluble in aqueous phosphate buffer (pH 8.0), and the complexation of naphthalene derivatives was investigated by 1H-NMR and fluorescence titrations. The binding studies demonstrated that the cyclophane cavity remains open and accessible to appropriate substrates even at higher dendritic generations. The 1:1 complexes formed in aqueous buffer were of similar stability to those formed by the unbranched core 9 (Ka between 1000 and 10000 1 mol-1, 300 K). Investigations with the fluorescent probe 6-(p-toluidino)naphthalene-2-sulfonate (12) showed that the micropolarity at the dendrophane core decreases with increasing generation number.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780803
