Self-assembly behavior of inclusion complex formed by b-cyclodextrin with a-aminopyridine

Zhao, Yanli; Liu, Yu

doi:10.1360/03yb0169

Cited by 8 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This contrasts with the ability of lactones to form inclusion complexes with cyclodextrins, such as the ε-caprolactone/β-CD inclusion complex [ 24 ]. However, the inclusion of nitrogenous heterocyclic bases such as, e.g., adenine [ 25 ], bipyridines [ 26 ] or α-aminopyridine [ 27 ] into β-CD has been reported in the literature. As far as we know, inclusion complexes between DMAP and β-cyclodextrin have never been reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

Meimoun¹,

Phuphuak

Miyamachi³

et al. 2022

Molecules

View full text Add to dashboard Cite

Cyclodextrins (CDs) are cyclic oligosaccharides used in many fields. Grafting polymers onto CDs enables new structures and applications to be obtained. Polylactide (PLA) is a biobased, biocompatible aliphatic polyester that can be grafted onto CDs by -OH-initiated ring-opening polymerization. Using 4-dimethylaminopyridine (DMAP) as an organocatalyst, a quantitative functionalization is reached on native α-, β-, γ- and 2,3-dimethyl- β-cyclodextrins. Narrow molecular weight distributions are obtained with the native CDs (dispersity < 1.1). The DMAP/β-CD combination is used as a case study, and the formation of an inclusion complex (1/1) is shown for the first time in the literature, which is fully characterized by NMR. The inclusion of DMAP into the cavity occurs via the secondary rim of the β-CD and the association constant (Ka) is estimated to be 88.2 M−1. Its use as an initiator for ring-opening polymerization leads to a partial functionalization efficiency, and thus a more hydrophilic β-CD-PLA conjugate than that obtained starting from native β-CD. Polymerization results including also the use of the adamantane/β-CD inclusion complex as an initiator suggest that inclusion of the DMAP catalyst into the CD may not occur during polymerization reactions. Rac-lactide does not form an inclusion complex with β-CD.

show abstract

Section: Resultsmentioning

confidence: 99%

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

Meimoun¹,

Phuphuak

Miyamachi³

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…However, CE does not give direct information on chemical and structural mechanism of the interactions. This requires the use of other techniques as X-ray crystallography [50], circular dichroism [51,52], fluorescence [51,52] and the most important one, nuclear magnetic resonance (NMR) spectroscopy [50][51][52][53]. More detailed discussion on the mechanism of chiral recognition by CDs can be found in two recent reviews published in 2004 by Chankvetadze [54] and Dodziuk et al [55].…”

Section: Mechanism Of Chiral Recognition By Cdsmentioning

confidence: 99%

Recent advances in pharmaceutical applications of chiral capillary electrophoresis

Hoogmartens

Schepdael

2006

Journal of Pharmaceutical and Biomedical Analysis

108

View full text Add to dashboard Cite

“…Crown ethers [7][8][9][10][11][12][13], cryptands [14][15][16][17][18], cyclodextrins [19][20][21][22], cucurbit[n]urils [23][24][25], and calix[n]arenes [26,27] have been universally used as hosts to fabricate various supramolecular assemblies, which have great potential in molecular devices, chemosensors, and nano materials. Paraquat ( Figure 1) and its derivatives (N,N′-dialkyl-4,4′-bipyridinium salts) are common guests in the field of pseudorotaxanes and rotaxanes [28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

A new cryptand/paraquat [2]pseudorotaxane

Zheng

Huang

et al. 2010

Sci. China Chem.

View full text Add to dashboard Cite

A new cryptand/paraquat [2]pseudorotaxane and its crown ether analog were synthesized and characterized by proton NMR, mass spectrometry, and single crystal X-ray analysis. The Job plots based on proton NMR data demonstrated that both the complex between cryptand 1 and paraquat derivative 2a and the complex between bis(p-phenylene)-34-crown-10 (3) and paraquat derivative 2b have 1:1 stoichiometry in solution. The apparent association constants (K a,exp ) of 1·2a and 3·2b calculated for 1:1 complexes were 1.4 ( 0.2)  10 4 and 4.7 ( 0.5)  10 2 M 1 , respectively. X-ray analysis showed that 1·2a is stabilized by ten hydrogen bonds and face-to-face -stacking interactions in the solid state, while 3·2b is stabilized by four hydrogen bonds and face-to-face -stacking interactions. As well as in the X-ray structure of 1·2c, a water molecule acts as a hydrogen bridge between the -pyridinium protons of 2a and the ether oxygen atoms of 1 in 1·2a. The successful preparation of 1·2a demonstrated that the tert-butyl group is not big enough to be a stopper for rotaxanes based on 1. host-guest system, self-assembly, pseudorotaxane, cryptand, paraquat

show abstract

Self-assembly behavior of inclusion complex formed by b-cyclodextrin with a-aminopyridine

Abstract: Science in China Press. It incorporates referee's comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document.

Cited by 8 publications

References 14 publications

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

Recent advances in pharmaceutical applications of chiral capillary electrophoresis

A new cryptand/paraquat [2]pseudorotaxane

Contact Info

Product

Resources

About