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• W2072738269 endingPage "16921" @default.
• W2072738269 startingPage "16911" @default.
• W2072738269 abstract "We designed and synthesized the three molecular tweezers 1 a–c4+ containing an electron acceptor 4,4′-bipyridinium (BPY2+) unit in each of the two arms and an (R)-2,2′-dioxy-1,1′-binaphthyl (BIN) unit that plays the role of chiral centre and the hinge of the structure. Each BPY2+ unit is connected to the BIN hinge by an alkyl chain formed by two- (1 a4+), four- (1 b4+), or six-CH2 (1 c4+) groups. The behavior of 1 a–c4+ upon chemical or photochemical reduction in the absence and in the presence of cucurbit[8]uril (CB[8]) or cucurbit[7]uril (CB[7]) as macrocyclic hosts for the bipyridinium units has been studied in aqueous solution. A detailed analysis of the UV/Vis absorption and circular dichroism (CD) spectra shows that the helicity of the BIN unit can be reversibly modulated by reduction of the BPY2+ units, or by association with cucurbiturils. Upon reduction of 1 a–c4+ compounds, the formed BPY+. units undergo intramolecular dimerization with a concomitant change in the BIN dihedral angle, which depends on the length of the alkyl spacers. The alkyl linkers also play an important role in association to cucurbiturils. Compound 1 a4+, because of its short carbon chain, associates to the bulky CB[8] in a 1:1 ratio, whereas in the case of the smaller host compound CB[7] a 1:2 complex is obtained. Compounds 1 b4+ and 1 c4+, which have longer linkers, associate to two cucurbiturils regardless of their sizes. In all cases, association with CB[8] causes an increase of the BIN dihedral angle, whereas the formation of CB[7] complexes causes an angle decrease. Reduction of the CB[8] complexes results in an enhancement of the BPY+. dimerization with respect to free 1 a–c4+ and causes a noticeable decrease of the BIN dihedral angle, because the BPY+. units of the two arms have to enter into the same macrocycle. The dimer formation in the CB[8] complexes characterized by a 1:2 ratio implies the release of one macrocycle showing that the binding stoichiometry of these host–guest complexes can be switched from 1:2 to 1:1 by changing the redox state of the guest. When the reduction is performed on the CB[7] complexes, dimer formation is totally inhibited, as expected because the CB[7] cavity cannot host two BPY+. units." @default.
• W2072738269 created "2016-06-24" @default.
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• W2072738269 date "2012-11-07" @default.
• W2072738269 modified "2023-09-27" @default.
• W2072738269 title "Chiral Supramolecular Switches Based on (<i>R</i>)-Binaphthalene-Bipyridinium Guests and Cucurbituril Hosts" @default.
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• W2072738269 doi "https://doi.org/10.1002/chem.201202378" @default.
• W2072738269 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23136090" @default.
• W2072738269 hasPublicationYear "2012" @default.
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