Novel pseudo[2]rotaxanes constructed by the self-assembly of dibenzyl tetramethylene bis-carbamate derivatives and per-ethylated pillar[5]arene

Author(s): Shuhan Xiong ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Xiaoning Zhang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Lu-Bo Meng ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Juli Jiang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Chen Lin ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Leyong Wang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2015

Journal: Chemical Communications

Publisher: Royal Society of Chemistry (RSC)

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Abstract

Novel pseudo[2]rotaxanes based on per-ethylated pillar[5]arene and neutral guests G1/ G7 were successfully constructed. Particularly, the pseudo[2]rotaxane constructed from per-ethylated pillar[5]arene and G7 showed photoresponsive properties.

Abstract

Novel neutral guest molecules, G1–G7, are studied for their host–guest complexation with per-ethylated pillar[5]arene ( EtP[5]A). Among them, G1 and G7, dibenzyl tetramethylene bis-carbamate derivatives, are found to afford a novel stable pseudo[2]rotaxane with EtP[5]A, respectively, and G7⊂EtP[5]A shows photoresponsive properties.

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The widespread use of controlled molecular-level motion in key natural processes suggests that great rewards could come from bridging the gap between the present generation of synthetic molecular systems, which by and large rely upon electronic and chemical effects to carry out their functions, and the machines of the macroscopic world, which utilize the synchronized movements of smaller parts to perform specific tasks. This is a scientific area of great contemporary interest and extraordinary recent growth, yet the notion of molecular-level machines dates back to a time when the ideas surrounding the statistical nature of matter and the laws of thermodynamics were first being formulated. Here we outline the exciting successes in taming molecular-level movement thus far, the underlying principles that all experimental designs must follow, and the early progress made towards utilizing synthetic molecular structures to perform tasks using mechanical motion. We also highlight some of the issues and challenges that still need to be overcome.

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para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.

Tomoki Ogoshi, Suguru Kanai, Shuhei Fujinami … (2008)

Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3.O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host-guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.