A phenyl glycinol appended calix[4]arene film for chiral detection of ascorbic acid on gold surface

Akpınar, Merve; Temel, Farabi; Tabakci, Begüm; Ozcelik, Egemen; Tabakcı, Mustafa

doi:10.1016/j.ab.2019.113373

Cited by 28 publications

(5 citation statements)

References 52 publications

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“…Kaliksarenler, kendine has üç boyutlu yapıları sayesinde nötral moleküller, katyon ve anyonlar, biyolojik moleküller, uçucu organik bileşiklerin (UOB) tanınması yada algılanması için yaygın bir şekilde kullanılmaktadır (Erdemir, 2016;Temel, 2016;Akpinar, 2019;Ozcelik, 2019b;Temel, 2020a;2020b). Bu çalışmada, sulu ortamdan fenolik türleri uzaklaştırmak için, merrifield reçinesine desteklenmiş kaliksaren dinitro türevi hazırlandı (Şekil 1).…”

Section: Bulgular (Results)unclassified

Merrifield Reçi̇nesi̇ne Desteklenmi̇ş Kali̇ks[4]aren Di̇ni̇tro Türevi̇ni̇n Sulu Ortamdaki̇ Fenoli̇k Türlere Karşi Ekstraksi̇yon Özelli̇kleri̇ni̇n İncelenmesi̇

Temel¹

2020

Konya Journal of Engineering Sciences

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Bu çalışmada, Merrifield reçinesine desteklenmiş kaliks[4]aren dinitro türevi (DNK[4]MR) hazırlanarak, sulu ortamda bulunan önemli organik kirleticilerden olan fenol (FEN), p-klorofenol (PKF), m-nitrofenol (MNF) ve p-nitrofenol (PNF) gibi bazı fenolik türlere karşı ekstraksiyon özellikleri incelendi. Sentezlenen bileşiklerin, FT-IR analizleri ile karakterizasyonları gerçekleştirildi. Sonuçlara göre, yukarıda bahsi geçen fenolik türlere karşı sırasıyla % 24,3, 40,5, 62,4 ve 65,9 ekstraksiyon verileri elde edildi. Ayrıca, farklı fenolik tür konsantrasyonlarına karşı DNK[4]MR'nin ekstraksiyon özellikleri incelendi. Son olarak, DNK[4]MR'nin fenolik türlere karşı ekstraksiyon kabiliyetlerinin ayrıntılı bir şekilde incelenmesi için farklı konsantrasyonlarda ligand çözeltileri hazırlanarak log D'ye karşı log [L] grafiği çizilerek etkileşim sonucu oluşan ekstraksiyon denge sabitleri (Kex) hesaplandı. Hem literatür bilgileri hem de yapılan bu çalışmanın sonuçlarına göre, kaliksaren türevlerinin kendisine özgü üç boyutlu yapısı ve hidrojen bağı yapabilme kabiliyetleri sayesinde, fenolik türlerin sulu ortamlardan uzaklaştırılması konusunda oldukça kullanışlı olabileceklerini göstermiştir.

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Section: Bulgular (Results)unclassified

Merrifield Reçi̇nesi̇ne Desteklenmi̇ş Kali̇ks[4]aren Di̇ni̇tro Türevi̇ni̇n Sulu Ortamdaki̇ Fenoli̇k Türlere Karşi Ekstraksi̇yon Özelli̇kleri̇ni̇n İncelenmesi̇

Temel¹

2020

Konya Journal of Engineering Sciences

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“…These four compounds are derived from each other. The first of these compounds is the p - tert -butyl calix[4]arene compound which is called as calix[4]arene1 (the basic calix[4]arene compound) and the calix[4]arene2 molecule is obtained by removing of tert -butyl groups of calix[4]arene1 compound [ 42 , 43 ]. The calix[4]arene3 and the calix[4]arene4 compounds are the structures formed by derivatizing calix[4]arene2 compound, and the IUPAC namings are 25,27-bis(3-mercaptopropoxy)-26,28-dihydroxy calix[4]arene and 5,17-Bis[N-(4-carboxypiperidino)methyl]-25,27-bis(3-mercaptopropoxy)-26,28-dihydroxy calix[4]arene, respectively [ 32 ].…”

Section: Methodsmentioning

confidence: 99%

The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing

Yüksel

Köse

Fellah

2021

J Incl Phenom Macrocycl Chem

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While the world is in search of a vaccine that can cure COVID-19 disease, favipiravir is the most commonly used antiviral drug in the treatment of patients during the pandemic process. In this study, we investigated the host–guest interaction between the popular supramolecule calix[4]arene derivatives and the favipiravir drug by using the DFT (Density Functional Theory) method. The B3LYP hybrid method and 6-31G (d,p) basis set were utilized to determine the optimized structures of the host and guest molecules and their complexes. The negative adsorption energy (∆E) and adsorption enthalpy (∆H) calculated for the complexes formed between calix[4]arene compounds and favipiravir drug molecule mentioned that adsorption of favipiravir molecule was an exothermic process on calix[4]arene structures. On the other hand, among the calixarene derivatives in the study, Gibbs free energy change (∆G) value for the adsorption was only negative on calix[4]arene4 molecule. The infrared spectroscopy (IR) calculations were performed by examining the C=O, O–H and NH 2 vibrational frequencies to see the adsorption behavior in the favipiravir-calix[4]arene complex. After adsorption of the favipiravir molecule, HOMO–LUMO gap values decreased significantly for the structures and therefore electrical conductivity increased proportionally. In addition, sensor response factors, Fermi energy levels and workfunction changes of calix[4]arene derivatives were calculated and examined. Charge transfer between the four calix[4]arene compounds and the favipiravir molecule has occurred after adsorption. This attributes that calix[4]arene derivatives can be used as a well-suited favipiravir sensor (electronic and workfunction) and adsorbent at room temperature. Based on the calculations made to see the solvent effect on the adsorption of favipiravir it was determined that it did not affect the interaction between the drug molecule and the calix[4]arene compound too much and the adsorption energy turned into a slightly less negative value.

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“…Chirality in calixarenes may derive from binding (at least) one chiral subunit to the rims or asymmetric placement of achiral subunits on the macrocycle [73][74][75]. Akpinar et al reported a simple and quick chiral discrimination strategy for ascorbic acid (AA) enantiomers based on calixarenes films (Figure 6) [76]. A chiral calix [4]arene-bearing chiral phenyl glycinol moiety on the lower rim and a thiol moiety on the upper rim were deposited on the gold surface of the QCM electrode.…”

Section: Chiral Recognition Layer From Supermolecular Structuresmentioning

confidence: 99%

“…Figure 6:The chiral calix[4]arene layer as a selector for enantioselective adsorption of ascorbic acid in the QCM system. Redrawn from[76].…”

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confidence: 99%

Design of surface nanostructures for chirality sensing based on quartz crystal microbalance

Ma¹,

Xiao²,

Ji³

2022

Beilstein J. Nanotechnol.

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Quartz crystal microbalance (QCM) has been widely used for various sensing applications, including chirality detection due to the high sensitivity to nanogram or picogram mass changes, fast response, real-time detection, easy operation, suitability in different media, and low experimental cost. The sensing performance of QCM is dependent on the surface design of the recognition layers. Various strategies have been employed for studying the relationship between the structural features and the specific detection of chiral isomers. This review provides an overview of the construction of chiral sensing layers by various nanostructures and materials in the QCM system, which include organic molecules, supermolecular assemblies, inorganic nanostructures, and metal surfaces. The sensing mechanisms based on these surface nanostructures and the related potentials for chiral detection by the QCM system are also summarized.

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A phenyl glycinol appended calix[4]arene film for chiral detection of ascorbic acid on gold surface

Cited by 28 publications

References 52 publications

Merrifield Reçi̇nesi̇ne Desteklenmi̇ş Kali̇ks[4]aren Di̇ni̇tro Türevi̇ni̇n Sulu Ortamdaki̇ Fenoli̇k Türlere Karşi Ekstraksi̇yon Özelli̇kleri̇ni̇n İncelenmesi̇

Merrifield Reçi̇nesi̇ne Desteklenmi̇ş Kali̇ks[4]aren Di̇ni̇tro Türevi̇ni̇n Sulu Ortamdaki̇ Fenoli̇k Türlere Karşi Ekstraksi̇yon Özelli̇kleri̇ni̇n İncelenmesi̇

The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing

Design of surface nanostructures for chirality sensing based on quartz crystal microbalance

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