Kaliks[4]aren bazlı kiral reseptörlerin sentezi

Abstract

Bu çalışmada kiral asit klorür türevleri (1, 2 ve 3) kaliks[4]aren ile etkileştirilerek p-tert-bütilkaliks[4]arenin mono ve diamit türevleri (4, 14 ve 15) sentezlenmiştir. Ayrıca kiral ve akiral primer amin türevleri, kaliks[4]arenin diester türeviyle etkileştirilerek altı tane diamit, bir tane de mono amit türevi (5, 6, 7, 8, 9, 10 ve 16) elde edilmiştir. Elde edilen diamit türevlerinden üç tanesi indirgenmiştir (11, 12 ve 13). Ayrıca sentezlenen bazı amitlerin H2PO4- ve HSO4- anyonlarına karşı anyon tanınma özellikleri 1H NMR spektroskopisi kullanılarak incelenmiştir. Birleşme oranları Job Plot analizi ile birleşme sabitleri ise en küçük kareler metodu kullanılarak belirlenmiştir.Gerçekleştirilen tüm reaksiyonlar İTK ile izlenmiş ve elde edilen ürünler kolon kromatografisi ile saflaştırılarak yapıları IR, 1H NMR, 13C NMR ve elementel analiz teknikleriyle aydınlatılmıştır.

In this study, mono and diamide derivatives of p-tert-butylcalix[4]arenes (4, 14 and 15) have been synthesized from the reaction of calix[4]arene with chiral acid chloride derivatives (1, 2 and 3). In addition to this, a mono and six diamide derivatives (5, 6, 7, 8, 9, 10 and 16) have been synthesized from the reaction of diester derivative of caliks[4]arene with chiral and achiral primary amine derivatives. The three of diamide derivatives obtained (11, 12 and 13) have been reduced into the corresponding diamine derivatives. Moreover, anion recognition capability of some of the synthesized amides towards H2PO4- and HSO4- by 1H NMR spectroscopy was investigated. The association ratio was determined by using Job plots and the association constants were determined by using nonlinear least-squares fitting method.The reactions were monitored by TLC and pure compounds were obtained after crystallysation, column chromatography or both. The structures of synthesized compounds were identified by FT-IR, 1H NMR, 13C NMR and elemental analysis.