Fig. 5: Double stopper-exchange protocol for the synthesis of rotaxanes 4c-d and shuttle 5, including shuttling via DA and retroDA reactions. | Communications Chemistry

Fig. 5: Double stopper-exchange protocol for the synthesis of rotaxanes 4c-d and shuttle 5, including shuttling via DA and retroDA reactions.

From: Conjugated bis(enaminones) as effective templates for rotaxane assembly and their post-synthetic modifications

Fig. 5

a Synthesis of rotaxanes 4c-d; b Synthesis of shuttle 5 and its chemical interconversion. Reaction conditions: (i) 2,2-diphenylethylamine (2.2 equiv), TCE, 100 °C, 12 h; (ii) 9-(aminomethyl)anthracene (2.2 equiv), TCE, 100 °C, 12 h; (iii) N1-(4-(aminomethyl)benzyl)-N4,N4-dibenzylsuccinamide (3 equiv), THF, 60 °C, 5 h (70%); (iv) p-xylylenediamine (8 equiv), isophthaloyl dichloride (8 equiv), Et3N (24 equiv), CHCl3, 25 °C, 4 h (13%); (v) cyclopentadiene, DMSO, 70 °C, 12 h (39%); (vi) 165 °C, 0.5 mm Hg, 1 h (65%).

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