Cyclodextrin Rotaxane with Switchable Pirouetting

Qi Wei Zhang; Jaroslav Zajíček; Bradley D. Smith

doi:10.1021/acs.orglett.8b00655

Cyclodextrin Rotaxane with Switchable Pirouetting

Qi Wei Zhang
, Jaroslav Zajíček
, Bradley D. Smith^*

^*Corresponding author for this work

University of Notre Dame

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

A [1]rotaxane with two threaded α-cyclodextrin (α-CD) wheels was synthesized in 92% yield using a one-pot process at room temperature that employed spontaneous α-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded α-CD wheels around the encapsulated dumbbell was switched "ON" or "OFF" by the presence of chemical additives that controlled boronate ester bond formation between the interlocked components.

Original language	English
Pages (from-to)	2096-2099
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.8b00655
State	Published - 6 Apr 2018
Externally published	Yes

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title = "Cyclodextrin Rotaxane with Switchable Pirouetting",

abstract = "A [1]rotaxane with two threaded α-cyclodextrin (α-CD) wheels was synthesized in 92\% yield using a one-pot process at room temperature that employed spontaneous α-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded α-CD wheels around the encapsulated dumbbell was switched {"}ON{"} or {"}OFF{"} by the presence of chemical additives that controlled boronate ester bond formation between the interlocked components.",

author = "Zhang, \{Qi Wei\} and Jaroslav Zaj{\'i}{\v c}ek and Smith, \{Bradley D.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = apr,

day = "6",

doi = "10.1021/acs.orglett.8b00655",

language = "英语",

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journal = "Organic Letters",

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T1 - Cyclodextrin Rotaxane with Switchable Pirouetting

AU - Zhang, Qi Wei

AU - Zajíček, Jaroslav

AU - Smith, Bradley D.

PY - 2018/4/6

Y1 - 2018/4/6

N2 - A [1]rotaxane with two threaded α-cyclodextrin (α-CD) wheels was synthesized in 92% yield using a one-pot process at room temperature that employed spontaneous α-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded α-CD wheels around the encapsulated dumbbell was switched "ON" or "OFF" by the presence of chemical additives that controlled boronate ester bond formation between the interlocked components.

AB - A [1]rotaxane with two threaded α-cyclodextrin (α-CD) wheels was synthesized in 92% yield using a one-pot process at room temperature that employed spontaneous α-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded α-CD wheels around the encapsulated dumbbell was switched "ON" or "OFF" by the presence of chemical additives that controlled boronate ester bond formation between the interlocked components.

UR - https://www.scopus.com/pages/publications/85045135814

U2 - 10.1021/acs.orglett.8b00655

DO - 10.1021/acs.orglett.8b00655

M3 - 文章

C2 - 29542930

AN - SCOPUS:85045135814

SN - 1523-7060

VL - 20

SP - 2096

EP - 2099

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Cyclodextrin Rotaxane with Switchable Pirouetting

Abstract

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