Benzotiyazol ve naftil grupları taşıyan kaliks[4]aren türevlerinin sentezi ve metal iyonları ile etkileşimlerinin incelenmesi
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Tarih
2020
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Selçuk Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Kaliksarenler, fonksiyonlardırılması kolay ve çok fazla olan, anyon, katyon ve nötral türlerle kompleks yapabilme (konuk-konak kompleksleşme), farklı büyüklükte molekül boşluğuna sahip olması gibi bir çok avantajı olan ve literatürde oldukça ilgi gören bileşiklerdir. Bu çalışmada da kaliks[4]aren bileşikleri, Schiff bazı ile türevlendilerek yeni supramoleküler bileşikler sentezlendi ve bazı metal iyonları ile etkileşimleri spektrofotometrik olarak incelendi. Bu amaçla 2-aminobenzotiyofenol (1) ve p-hidroksibenzaldehit (2) bileşiği etkileştirilerek benzotiyazol bileşiği (3) elde edildi. Bu bileşik trifloroasetikasit ve hekzametilentetraamin ile etkileştirilip aldehit türevli benzotiyazol bileşiği (4) elde edildi. p-ter-bütilfenol kullanılarak p-ter-bütilkaliks[4]aren sentezlendikten sonra, p-ter-bütilkaliks[4]aren (5), metilbromasetat ile K2CO3 varlığında kuru aseton içerisinde etkileştirilerek diester türevine (6) dönüştürüldü. Diester türevli kaliks[4]aren bileşiği tris(2-aminoetil)amin bileşiği ile etkileştirilerek amit türevi (7) elde edildi. Amit türevli kaliks[4]aren (7) aldehit grubu taşıyan benzotiyazol (4) ve 2-hidroksinaftaldehit ile etkileştirilerek 8 ve 9 numaralı bileşikler elde edildi. Sentezlenen bileşiklerinin yapıları spektroskopik teknikler (FTIR, 1H NMR) ile aydınlatıldı. Bu bileşiklerin bazı metal katyonlarına karşı floresans özellikleri UV-Vis. ve floresans spektroskopik teknikleri kullanılarak incelendi. Sonuç olarak 8 numaralı bileşiğin Zn+2 iyonu ile 9 numaralı bileşiğin ise Al+3 iyonu ile etkileşim gösterdiği bulundu.
Calixarenes are also very interesting compounds in the literature which are easy to function and have many advantages such as complexity (guest-host complexation) and having different sized molecular cavities in anion, cation and neutral environments. In this study, calix[4]arene compounds will be synthesized with Schiff base and new supramolecular compounds were synthesized and their interaction with some metal ions was examined spectrophotometrically. For this purpose, by reacting the 2-aminobenzothiophenol (1) and p-hydroxybenzaldehyde compound (2), the benzothiazole compound (3) was obtained. This compound was reacted with trifluoroacetic acid and hexamethylenetetraamine to give the aldehyde-derived benzothiazole (4). p-tert-butyl calix[4]arene is synthesized using p-tert-butyl phenol, then p-tert-butylcalix[4]arene (5) was converted to diester derivative (6) in the presence of methylbromoacetate and K2CO3 in dry acetone. The diester-derived calix[4]arene compound will be reacted with the tris (2-aminoethyl) amine compound to give the amide derivative (7). Amide-derived calix[4]arene (7) was reacted with aldehyde derivatives of benzothiazole (4) and 2-hydroxynaphthaldehyde to give compounds 8 and 9. The structures of the synthesized compounds were elucidated by spectroscopic techniques (FTIR, 1H NMR). The fluorescence properties of these compounds against some metal cations were examined using UV-Vis. and fluorescence spectroscopic techniques. As a result, it was found that compound 8 interacts with Zn +2 ion and compound 9 with Al +3 ion.
Calixarenes are also very interesting compounds in the literature which are easy to function and have many advantages such as complexity (guest-host complexation) and having different sized molecular cavities in anion, cation and neutral environments. In this study, calix[4]arene compounds will be synthesized with Schiff base and new supramolecular compounds were synthesized and their interaction with some metal ions was examined spectrophotometrically. For this purpose, by reacting the 2-aminobenzothiophenol (1) and p-hydroxybenzaldehyde compound (2), the benzothiazole compound (3) was obtained. This compound was reacted with trifluoroacetic acid and hexamethylenetetraamine to give the aldehyde-derived benzothiazole (4). p-tert-butyl calix[4]arene is synthesized using p-tert-butyl phenol, then p-tert-butylcalix[4]arene (5) was converted to diester derivative (6) in the presence of methylbromoacetate and K2CO3 in dry acetone. The diester-derived calix[4]arene compound will be reacted with the tris (2-aminoethyl) amine compound to give the amide derivative (7). Amide-derived calix[4]arene (7) was reacted with aldehyde derivatives of benzothiazole (4) and 2-hydroxynaphthaldehyde to give compounds 8 and 9. The structures of the synthesized compounds were elucidated by spectroscopic techniques (FTIR, 1H NMR). The fluorescence properties of these compounds against some metal cations were examined using UV-Vis. and fluorescence spectroscopic techniques. As a result, it was found that compound 8 interacts with Zn +2 ion and compound 9 with Al +3 ion.
Açıklama
Anahtar Kelimeler
Kaliks[4]aren, Floresans, Benzotiyazol, Calix[4]arene, Fluorescence, Benzothiazol
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Majeed, O.S.M. (2020). Benzotiyazol ve Naftil Grupları Taşıyan Kaliks[4]aren Türevlerinin Sentezi ve Metal İyonları ile Etkileşimlerinin İncelenmesi. ( Yüksek Lisans Tezi). Selçuk Üniversitesi, Fen Bilimleri Enstitüsü, Konya.
