Farklı substitüentler taşıyan bazı pirol türevlerinin sentezi
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Dosyalar
Tarih
2019
Yazarlar
Dergi Başlığı
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Cilt Başlığı
Yayıncı
Trakya Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
İletken polimerlerden olan polipiroller farklı pirol türevi monomerlerden yola çıkılarak ve farklı sentez yöntemleri ile elde edilebilmektedir. Pirol monomerlerinin yapısında bulunan substitüentler ve polimerizasyon yöntemi elde edilen polimerin iletkenliğini ve diğer fiziksel özelliklerini belirlemektedir. Bu çalışmada sentezlenen farklı substitüentler taşıyan pirol türevlerinin yapıları IR, 1 H NMR, 13 C NMR ve Kütle spektroskopisi kullanılarak tanımlanmıştır ve bu bileşikler monomer olarak kullanılabilme potansiyeline sahiptir. Bu amaçla N-substitüe pirollerin sentezi Clauson Kaas yöntemi kullanılarak 2,5-dimetoksitetrahidrofuran ve primer alkil ve aril aminlerden başlayarak gerçekleştirilmiştir. Bu yöntemle 1-(4-(benziloksi)fenil)-1H-pirol, 1(benzo[d][1,3]dioksol-5-il)-1H-pirol, 2-(1H-pirol-1-il)etanol ve 2-(1H-pirol-1-il)etil dodekanoat olmak üzere 4 farklı N-substitüe pirol’ün sentezi farklı reaksiyon koşulları kullanılarak başarılmıştır. 4-(1H-pirolil)benzensülfonik asit, 1-allil-1H-pirol, 1H-pirol-1ol sentezleri ise başarılamamıştır. C-substitüe pirollerin sentezi primer aminlerden elde edilmiş çeşitli iminodiasetat türevlerinin, uygun bazlar (MeONa, EtONa) ve dietiloksalattan bazik ortamda kondenzasyon reaksiyonu ile gerçekleştirilmiştir. Bu yöntemle de dimetil 3,4-dihidroksi-1H-pirol-2,5-dikarboksilat ve dietil 1-benzil-3,4- dihidroksi-1H-pirol-2,5-dikarboksilat olmak üzere 2 farklı C-substitüe pirol’ün sentezi gerçekleştirilmiş, dietil 1-benzil-3,4-dihidroksi-1H-pirol-2,5-dikarboksilat’dan yola çıkılarak pirol bazlı 3 farklı makrosiklik ligand sentezlenmiştir.
The polypyrroles from the conducting polymers can be obtained from different pyrrole-derived monomers by different routes and by different synthesis methods. Substituents in the structure of the pyrrole monomers and the polymerisation method determine the conductivity and other physical properties of the resulting polymer. The structures of pyrrole derivatives including different substituents synthesized in this work were identified using IR, 1 H NMR, 13 C NMR and Mass spectroscopy, and these compounds have the potential to be used as monomers. For this purpose, the synthesis of N-substituted pyrroles was carried out using the Clauson Kaas method starting from 2,5dimethoxytetrahydrofuran and the primer alkyl and aryl amines. By this method, synthesis of 1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole, 2-(1H-pyrrol-1-yl)ethanol and 2(1H-pyrrol-1-yl)ethyl dodecanoate were achieved using different reaction conditions. Synthesis of 4-(1H-pyrrolyl)benzenesulfonic acid, 1-allyl-1H-pyrrole, 1H-pyrrol-1-ol was unsuccessful. The synthesis of C-substituted pyrroles was carried out by condensation reaction of various iminodiacetate derivatives obtained from the primary amines with the appropriate bases (MeONa, EtONa) and diethyloxalate in basic medium. In this way, synthesis of two different C-substituted pyrroles, dimethyl 3,4-dihydroxy- 1H-pyrrole-2,5-dicarboxylate and diethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5dicarboxylate were realized. Three different pyrrole-based macrocyclic ligands were synthesized from diethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate.
The polypyrroles from the conducting polymers can be obtained from different pyrrole-derived monomers by different routes and by different synthesis methods. Substituents in the structure of the pyrrole monomers and the polymerisation method determine the conductivity and other physical properties of the resulting polymer. The structures of pyrrole derivatives including different substituents synthesized in this work were identified using IR, 1 H NMR, 13 C NMR and Mass spectroscopy, and these compounds have the potential to be used as monomers. For this purpose, the synthesis of N-substituted pyrroles was carried out using the Clauson Kaas method starting from 2,5dimethoxytetrahydrofuran and the primer alkyl and aryl amines. By this method, synthesis of 1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole, 2-(1H-pyrrol-1-yl)ethanol and 2(1H-pyrrol-1-yl)ethyl dodecanoate were achieved using different reaction conditions. Synthesis of 4-(1H-pyrrolyl)benzenesulfonic acid, 1-allyl-1H-pyrrole, 1H-pyrrol-1-ol was unsuccessful. The synthesis of C-substituted pyrroles was carried out by condensation reaction of various iminodiacetate derivatives obtained from the primary amines with the appropriate bases (MeONa, EtONa) and diethyloxalate in basic medium. In this way, synthesis of two different C-substituted pyrroles, dimethyl 3,4-dihydroxy- 1H-pyrrole-2,5-dicarboxylate and diethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5dicarboxylate were realized. Three different pyrrole-based macrocyclic ligands were synthesized from diethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate.
Açıklama
Anahtar Kelimeler
Substitüe Pirol, Sentez, Monomer, Makrosiklik Ligand, Substituted Pyrrole, Synthesis, Monomer, Macrocyclic Ligand
