2015
DOI: 10.1038/ncomms8590
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Mechanically selflocked chiral gemini-catenanes

Abstract: Mechanically interlocked and entangled molecular architectures represent one of the elaborate topological superstructures engineered at a molecular resolution. Here we report a methodology for fabricating mechanically selflocked molecules (MSMs) through highly efficient one-step amidation of a pseudorotaxane derived from dual functionalized pillar[5]arene (P[5]A) threaded by α,ω-diaminoalkane (DA-n; n=3–12). The monomeric and dimeric pseudo[1]catenanes thus obtained, which are inherently chiral due to the topo… Show more

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Cited by 179 publications
(77 citation statements)
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“…The most common member of the pillararene family, pillar [5]arene, contains five 1,4-dialkoxybenzene subunits bridged by methylene spacers. Each rim of the tube-shaped macrocycle is lined with five oxygen atoms, which results in an electron-rich cavity from which the host properties arise, leading to the use of pillar [5]arenes in the construction of inclusion complexes [2][3][4][5][6][7], rotaxanes [8][9][10][11][12][13][14][15] and other mechanically interlocked systems [16][17][18][19][20].…”
Section: Introductionmentioning
confidence: 99%
“…The most common member of the pillararene family, pillar [5]arene, contains five 1,4-dialkoxybenzene subunits bridged by methylene spacers. Each rim of the tube-shaped macrocycle is lined with five oxygen atoms, which results in an electron-rich cavity from which the host properties arise, leading to the use of pillar [5]arenes in the construction of inclusion complexes [2][3][4][5][6][7], rotaxanes [8][9][10][11][12][13][14][15] and other mechanically interlocked systems [16][17][18][19][20].…”
Section: Introductionmentioning
confidence: 99%
“…The inhibition of the oxygen-through-annulus rotation will lead to a pair of planar-chiral enantiomers. Three approaches, including rotaxanation, the introduction of a side ring into one ring unit, as well as the chemical modification of bulky groups onto the rims, have been exploited for constructing chiral pillar [5]arenes [18][19][20]. Bulky groups, such as cyclohexylmethyl, phenyl, of bulky groups onto the rims, have been exploited for constructing chiral pillar [5]arenes [18][19][20].…”
Section: Introductionmentioning
confidence: 99%
“…Three approaches, including rotaxanation, the introduction of a side ring into one ring unit, as well as the chemical modification of bulky groups onto the rims, have been exploited for constructing chiral pillar [5]arenes [18][19][20]. Bulky groups, such as cyclohexylmethyl, phenyl, of bulky groups onto the rims, have been exploited for constructing chiral pillar [5]arenes [18][19][20]. Bulky groups, such as cyclohexylmethyl, phenyl, or bithienyl groups, have been chemically grafted onto one or more hydroquinone ether units, and the oxygen-through-annulus rotation was restrained or completely stopped [21,22].…”
Section: Introductionmentioning
confidence: 99%
“…As a new class of macromolecules, pillar[n]arenes (5–15) have been extensively studied from their synthesis, functionalization and supramolecular chemistry since 2008313233343536. The first photo-responsive host-guest complexation based on pillar[6]arene and azobenzene-guest was reported by Huang in 201237.…”
mentioning
confidence: 99%