Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors

Temel, Farabi; Erdemir, Serkan; Tabakci, Begüm; Akpınar, Merve; Tabakcı, Mustafa

doi:10.1007/s00216-019-01705-5

Cited by 35 publications

(9 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[5][6][7][8] Therefore,t he breakthrough strategy and materials are still in demand for constructing the sensing system with rapid and simple assays of enantiomers.Q uartz crystal microbalance (QCM) is aconvenient and cost-effective technique for real-time chiral detection in wet or dry conditions. [9][10][11] As the sensing is according to the frequency shift of quartz oscillation, QCM system may provide ar apid and sensitive response on the adsorbed analytes.T he detection efficiencyo fQ CM mainly relies on the recognition layer on the electrode surface.Both chiral or achiral materials,w hich include cyclic macromolecules, [12,13] molecularly imprinted polymers, [14][15][16] metal-organic-frameworks (MOFs), [17,18] and amino acid derivatives, [19] etc. could be used as recognition layers.A lmost all the QCM sensing systems have focused on the design of organic sensing layers and the study of selectively detection of certain chiral molecules.H owever,t he coated organic selectors on the electrode surface may inevitably cause dissipation of oscillation due to their elasticity,w hich thus could make the detection responses from the electrode complex.…”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

et al. 2021

View full text Add to dashboard Cite

Quartz crystal microbalance (QCM) is one of the powerful tools for the studies of molecular recognition and chiral discrimination. Its efficiency mainly relies on the design of the functional sensitive layer on the electrode surface. However,t he organic sensitive layer may easily cause dissipation of oscillation or detachmentand weaken the signal transfer during the molecular recognition processes.I nt his work, we reveal for the first time that the bare metal surface without the organic selector layer has the capability for chiral recognition in the QCM system. During the adsorption of various chiral amino acids,r elatively higher selectivity of D-enantiomers on gold (Au) surface was shown by the QCM detection. Based on analyses of the surface crystalline structure and density functional theory calculations,wedemonstrate that the chiral nature of Au surface playsanimportant role in the selective binding of specific D-amino acids.These results may open new insights on chiral detection by QCM system. It will also promote the construction of novel chiral sensing systems with both efficient detection and separation capability.

show abstract

Section: Introductionmentioning

confidence: 99%

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[1][2][3] The ability to recognize substrates and form supramolecular complexes with them underlies the use of such compounds in sensory techniques and technology. [4][5][6] As well, the unique spatial structure of calix [4] arene allows the formation of so-called inherently chiral compounds, the chirality of which is based on the absence of planes of symmetry or the center of inversion due to the asymmetric placement of several achiral groups on the macrocyclic platform. Recently, special attention has been paid to such compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Calixarenes are widely used as molecular platforms for the design of specific receptors which are capable of high selectivity to recognize substrates close in size and properties—various cations, anions, and neutral molecules 1–3 . The ability to recognize substrates and form supramolecular complexes with them underlies the use of such compounds in sensory techniques and technology 4–6 . As well, the unique spatial structure of calix[4]arene allows the formation of so‐called inherently chiral compounds, the chirality of which is based on the absence of planes of symmetry or the center of inversion due to the asymmetric placement of several achiral groups on the macrocyclic platform.…”

Section: Introductionmentioning

confidence: 99%

Recognition of 1‐phenylethylamine enantiomers by thin solid films of inherently chiral calix[4]arene

et al. 2021

View full text Add to dashboard Cite

The enantiodiscrimination properties of stereomerically pure inherently chiral calix[4]arene acetic acids, as well as their esters and amides in relation to 1-phenylethylamine stereoisomers in liquid and gaseous phases were studied by means of proton magnetic resonance spectroscopy ( 1 H NMR) and quartz crystal microbalance (QCM) techniques. Series of QCM sensors with thin films of inherently chiral calix[4]arenes, immobilized on the quartz resonator surfaces by spin-coating and spreading drop methods have been fabricated. It was shown that sensors based on calix[4]arene acetic acids are able to recognize Rand S-forms of 1-phenylethylamine in gaseous phase under concentration level of 10-400 ppm.

show abstract

“…The detection efficiency of QCM mainly relies on the recognition layer on the electrode surface. Both chiral or achiral materials, which include cyclic macromolecules, [12, 13] molecularly imprinted polymers, [14–16] metal‐organic‐frameworks (MOFs), [17, 18] and amino acid derivatives, [19] etc. could be used as recognition layers.…”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

et al. 2021

View full text Add to dashboard Cite

Quartz crystal microbalance (QCM) is one of the powerful tools for the studies of molecular recognition and chiral discrimination. Its efficiency mainly relies on the design of the functional sensitive layer on the electrode surface. However, the organic sensitive layer may easily cause dissipation of oscillation or detachment and weaken the signal transfer during the molecular recognition processes. In this work, we reveal for the first time that the bare metal surface without the organic selector layer has the capability for chiral recognition in the QCM system. During the adsorption of various chiral amino acids, relatively higher selectivity of D‐enantiomers on gold (Au) surface was shown by the QCM detection. Based on analyses of the surface crystalline structure and density functional theory calculations, we demonstrate that the chiral nature of Au surface plays an important role in the selective binding of specific D‐amino acids. These results may open new insights on chiral detection by QCM system. It will also promote the construction of novel chiral sensing systems with both efficient detection and separation capability.

show abstract

Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors

Cited by 35 publications

References 61 publications

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

Recognition of 1‐phenylethylamine enantiomers by thin solid films of inherently chiral calix[4]arene

Chiral Recognition on Bare Gold Surfaces by Quartz Crystal Microbalance

Contact Info

Product

Resources

About