Download The Power of Click Chemistry for Molecular Machines and by Jason M. Spruell PDF

By Jason M. Spruell

The union of covalent and noncovalent chemistries manifested within the mechanical bond represents one of many nice chemical triumphs of the final part century. besides the fact that, until eventually lately, the coaching of robotically interlocked compounds has frequently been an inefficient and restricting procedure. This thesis presents an in depth account of the good strides taken to extend the factitious accessibility of donor-acceptor automatically interlocked molecules by way of the appliance of hugely effective and ultramild chemical alterations in the course of their template-directed synthesis. those new departures in synthesis have certainly performed a transformative function in that extra complicated, higher-order, and practical architectures – as soon as just a dream – at the moment are conveniently close by. in particular, the formation of mechanical bonds in larger order rotaxanes and catenanes has turn into ever more uncomplicated by utilizing hugely effective click on chemistries. The ensuing routinely interlocked compounds are useful molecular media for a bunch of functions together with details garage, mechanical actuation, and drug release.

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Tornoe CW, Christensen C, Meldal MJ (2002) Org. Chem. 67:3057–3064 6. Dichtel WR, Miljanic´ OŠ, Spruell JM, Heath JR, Stoddart JF (2006) J Am Chem Soc 128:10388–10390 7. Lutz JF (2007) Angew Chem Int Ed 46:1018–1025 8. Kolb HC, Sharpless KB (2003) Drug Discovery Today 8:1128–1137 9. Mobian P, Collin JP, Sauvage J-P (2006) Tetrahedron Lett 47:4907–4909 10. Aucagne V, Hanni KD, Leigh DA, Lusby PJ, Walker DB (2006) J Am Chem Soc 128:2186–2187 11. Miljanic´ OŠ, Dichtel WR, Mortezaei S, Stoddart JF (2006) Org Lett 8:4835–4838 12.

A constitutionally unsymmetrical monoprotected pseudorotaxane may be stoppered in the initial step (I), the protecting group removed in the second step (II), and then functionalized with a different type of stopper in the third step (III) to form a constitutionally unsymmetrical [2]rotaxane. , the branched [4]rotaxane described in this Chapter) to be assembled sequentially in one pot of the unmasked functionality. These sequences prove most efficient if they could be performed in one-pot, a goal that adds the requirements that each of the three (or more) steps must proceed to nearly quantitative conversion and that the reagents used in the beginning of the sequence must not interfere with those employed in subsequent steps.

In this context, we recently developed [16] a simple and high-yielding method for the synthesis of donor–acceptor rotaxanes [16–24] based on a threading-followed-by-stoppering approach [25–29] that utilizes the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) [30, 31]. Although we have employed [16, 20, 22] this method to prepare previously unavailable mechanically interlocked compounds, it is best suited for the template-directed synthesis [32–37] of [n]rotaxanes stoppered by identical bulky groups.

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