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Volumn 49, Issue 44, 2010, Pages 8260-8265

Mechanical bond formation by radical templation

Author keywords

Electrochemistry; Radical dimerization; Rotaxanes; Self assembly; Template directed synthesis

Indexed keywords

BIPYRIDINES; CYCLOBIS(PARAQUAT-P-PHENYLENE); ELECTRON-TRANSFER; INCLUSION COMPLEX; MECHANICAL BONDS; RADICAL CATIONS; RADICAL DIMERIZATION; RADICAL INTERACTIONS; ROTAXANES; TEMPLATE-DIRECTED SYNTHESIS; TEMPLATION; TRIETHANOLAMINES; VIOLOGENS;

EID: 78249272655     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004488     Document Type: Article
Times cited : (87)

References (149)
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    • -1 in MeCN at room temperature. For more details, see Ref. [24].
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    • 2(.) upon reduction, we carried out CV and SEC experiments on a 1:1 mixture (see Figures S6 and S8 in the Supporting Information)
    • 2(.) upon reduction, we carried out CV and SEC experiments on a 1:1 mixture (see Figures S6 and S8 in the Supporting Information).
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    • 2. Since we used an excess of TEOA, we expect that, at equilibrium, the dominant species will be the trisradical inclusion complex, although we hypothesize that some bisradical complex may also be present as a result of back electron transfer. See:, - 110.
    • 2. Since we used an excess of TEOA, we expect that, at equilibrium, the dominant species will be the trisradical inclusion complex, although we hypothesize that some bisradical complex may also be present as a result of back electron transfer. See:, R. Lomoth, T. Häupl, O. Johansson, L. Hammarström, Chem. Eur. J. 2002, 8, 102 - 110.
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    • This particular alkyne derivative was chosen as the stopper precursor for rotaxane formation on account of its two π-electron-deficient carbonyl groups adjacent to the C-C bond, a situation which lowers the lowest unoccupied molecular orbital (LUMO) of the alkyne and thus enhances the reaction rate associated with the 1,3-dipolar cycloaddition dramatically. See Ref. [29d]
    • This particular alkyne derivative was chosen as the stopper precursor for rotaxane formation on account of its two π-electron-deficient carbonyl groups adjacent to the C-C bond, a situation which lowers the lowest unoccupied molecular orbital (LUMO) of the alkyne and thus enhances the reaction rate associated with the 1,3-dipolar cycloaddition dramatically. See Ref. [29d].


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