Ester ve amit grupları taşıyan naftalimit türevli kaliks[4]aren bileşiklerinin sentezi ve floresans özelliklerinin 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
Bu çalışmada ester ve amit grupları taşıyan naftalimit türevli kaliks[4]aren bileşikleri sentezlendi. Başlangıç maddesi olarak 4-bromo-1,8-naftalikanhidrid (1) asetik asit içinde o-fenilendiamin (2) ile etkileştirilerek 3 numaralı bileşik sentezlendi. Elde edilen bileşik etilendiamin ile etkileştirilerek 4 numaralı bileşik elde edildi. Başlangıç maddesi olarak p-ter-bütil fenol kullanılarak sentezlenen p-ter-bütilkaliks[4]aren (5), metilbromasetat ile K2CO3 varlığında kuru aseton içerisinde etkileştirilerek diester türevine (6) dönüştürüldü. p-ter-Bütilkaliks[4]arenin diester türevi, hekzametilentetraamin ve trifloroasetikasit ile etkileştirilerek diester dialdehit türevli kaliks[4]aren bileşiği (7) elde edildi. 7 numaralı bileşik 4 numaralı bileşik ile etkileştirilerek hedeflenen 8 numaralı bileşik elde edildi. Çalışmanın ikinci aşamasında, diester türevli kaliks[4]aren bileşiği 3-morfolin-1-propilamin ile etkileştirilerek amit türevine (9) dönüştürüldükten sonra hekzametilentetraamin ve trifloroasetikasit ile etkileştirilerek diamit dialdehit türevli kaliks[4]aren bileşiği (10) sentezlendi. Son basamakta bu bileşik 4 numaralı bileşik ile etkileştirilip 11 numaralı bileşik elde edildi. Sentezlenen tüm bileşiklerin yapıları spektroskopik teknikler (FTIR, 1H-NMR) kullanılarak aydınlatıldı. Bu kaliks[4]aren türevlerinin bazı metal katyonlarına (Na+, Li+, Mg+2, Ni+2, Ba+2, Cu+2, Ca+2, Pb+2, Zn+2, Hg+2, Ag+, Co+2, Cd+2, Cr+3, Fe+2, Fe+3, Al+3, Mn+2) karşı floresans özellikleri metal perklorat tuzları ile etkileştirilerek UV-Vis., NMR ve floresans spektroskopik teknikleri kullanılarak incelendi.
In this study, naphthalimide derived calix[4]arene compounds carrying ester and amide groups were synthesized. Compound 3 was synthesized by reacting 4-bromo-1,8-naphthalic anhydride (1) as the starting material in acetic acid with o-phenylenediamine (2). The compound obtained was reacted with ethylenediamine to give compound 4. The p-tert-butyl[4]arene (5) synthesized using p-tert-butyl phenol as the starting material was converted to the diester derivative (6) by interacting with methylbromacetate in dry acetone in the presence of K2CO3. The diester derivative of p-tert-butylcalix [4]arene was reacted with hexamethylenetetraamine and trifluoroacetic acid to give diester dialdehyde-derived calix[4]arene compound (7). Compound 7 was reacted with compound 4 to give the desired compound 8. In the second step of the study, diester-derived calix[4]arene compound was converted to the amide derivative (9) by reacting with 3-morpholine-1-propylamine, and then reacted with hexamethylenetetraamine and trifluoroacetic acid to obtain diamide dialdehyde-derived calix[4]arene compound (10). In the last step, this compound was reacted with compound 4 to give compound 11. The structures of all synthesized compounds were identified using spectroscopic techniques (FTIR, 1H NMR). The fluorescence properties of these calix[4]arene derivatives against some metal cations (Na+, Li+, Mg2+, Ni2+, Ba2+, Cu2+, Ca2+, Pb2+, Zn2+, Hg2+, Ag+, Co2+, Cd2+, Cr3+, Fe2+, Fe3+, Al3+, Mn2+) were examined by interacting with metal perchlorate salts using UV-Vis., NMR and fluorescence spectroscopic techniques.
In this study, naphthalimide derived calix[4]arene compounds carrying ester and amide groups were synthesized. Compound 3 was synthesized by reacting 4-bromo-1,8-naphthalic anhydride (1) as the starting material in acetic acid with o-phenylenediamine (2). The compound obtained was reacted with ethylenediamine to give compound 4. The p-tert-butyl[4]arene (5) synthesized using p-tert-butyl phenol as the starting material was converted to the diester derivative (6) by interacting with methylbromacetate in dry acetone in the presence of K2CO3. The diester derivative of p-tert-butylcalix [4]arene was reacted with hexamethylenetetraamine and trifluoroacetic acid to give diester dialdehyde-derived calix[4]arene compound (7). Compound 7 was reacted with compound 4 to give the desired compound 8. In the second step of the study, diester-derived calix[4]arene compound was converted to the amide derivative (9) by reacting with 3-morpholine-1-propylamine, and then reacted with hexamethylenetetraamine and trifluoroacetic acid to obtain diamide dialdehyde-derived calix[4]arene compound (10). In the last step, this compound was reacted with compound 4 to give compound 11. The structures of all synthesized compounds were identified using spectroscopic techniques (FTIR, 1H NMR). The fluorescence properties of these calix[4]arene derivatives against some metal cations (Na+, Li+, Mg2+, Ni2+, Ba2+, Cu2+, Ca2+, Pb2+, Zn2+, Hg2+, Ag+, Co2+, Cd2+, Cr3+, Fe2+, Fe3+, Al3+, Mn2+) were examined by interacting with metal perchlorate salts using UV-Vis., NMR and fluorescence spectroscopic techniques.
Açıklama
Anahtar Kelimeler
Amit, Ester, Floresans, Kaliks[4]aren, Naftalimit, Amide, Calix[4]arene, Fluorescence, Naphthalimide
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Holmquist, F. G. (2020). Ester ve Amit Grupları Taşıyan Naftalimit Türevli Kaliks[4]Aren Bileşiklerinin Sentezi Ve Floresans Özelliklerinin İncelenmesi. (Yüksek Lisans Tezi). Selçuk Üniversitesi, Fen Bilimleri Enstitüsü, Konya.
