Bazı heterohalkalı organik bileşiklerin sentezleri ve spektroskopik incelemeleri
Küçük Resim Yok
Tarih
1992
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Ege Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
133 SUMMARY The structures of condensed aromatic systems are known very well for their formation of electron donor-acceptor (EDA) charge transfer complexes. The chiral condensed aromatic systems and chiral recognation of some EDA complexes of heteroaromatics and investigation of streoisomeric forms by *H and "C NMR spectroscopy and by chiral chromatography techniques have been widely studied by Mannschreck and his groups. Some of the condensed aromatic ring systems are known to exert luminescence. Thus in this project some chiral condensed aromatic ring systems have been synthesized. Heterocyclic selected compounds with high luminescence behaviour were fluorescein antracene and azlactone derivatives. The synthetic routes and purification methods of the selected compounds were discussed. The starting materials have been synthesized and then fluorescein, antracene and azlactone derivatives have been prepared. The selected derivative of fluorescein was methyl ether-ester, the fluorescein free acid was reacted with diazomethane. 9,10-Diaryl anthracene derivatives were prepared by the addition to carbonyl groups of 2-methyl anthraquinon with grignard reactives. The azlacton derivatives were formed by the condensation of the appropriate aromatic aldehydes with o-toluyl glisine and benzoyl glisine and then cyclization reaction was made. The structure of all molecules, which were synthesized was identified by their UV, mass, IR and NMR spectra. The yield, boiling and melting points and spectroscopic data were also determined and analyzed for these molecules. The compounds which were synthesized have been widely examined by134 1H and 1^C NMR spectroscopy. Also, the absorption and emission spectra have taken and their luminescence activities have been investigated. As seen the molecular structures of fluorescein and anthracene derivatives, ortho substituted aryl groups on these compound are expected to have restricted rotation around bond of attachement. Thus the rotational enantiomers of these compounds are expected to be detected in NMR spectroscopy due to magnetic non-equivalence of isotopic proton and carbon nuclei. The resolution of some of these isomers may become possible in chiral chromatography. This subject has been succeeded on fluorescein methyl- ether-ester. The *H NMR and **C NMR spectra of fluorescein methylether-ester have been detected the isomeric signals arising from the internal hindered rotation about the Cg-Cj bond. In this molecule, the Cg-Cj bond rotational axis have been served as an asymetric center and formed enantiomeric rot mers as a result of 180° rotation. The isomers have been separated on T.A.C. column. Then by using UV detector and polarimetric detector have been detected the isomeric peaks. The emission spectrum of this compound has been taken in different temperatures in relation to emission intensity. The same studies with NMR spectroscopy have been made on 2-methyl-9,10-diaryl anthracene and azlactone derivatives. But the isomeric signals of these compoundswere not seen in *H NMR or TC NMR spectra. So, in this study, the conformational isomers of restricted rotation about appropriate single bond were not detected at room temperature. A low temperature study is expected to show restricted rotational isomers. The emission spectra of azlactone derivatives has been studied and discussed for the substituent effects on emission intensities in derivatives
133 SUMMARY The structures of condensed aromatic systems are known very well for their formation of electron donor-acceptor (EDA) charge transfer complexes. The chiral condensed aromatic systems and chiral recognation of some EDA complexes of heteroaromatics and investigation of streoisomeric forms by *H and "C NMR spectroscopy and by chiral chromatography techniques have been widely studied by Mannschreck and his groups. Some of the condensed aromatic ring systems are known to exert luminescence. Thus in this project some chiral condensed aromatic ring systems have been synthesized. Heterocyclic selected compounds with high luminescence behaviour were fluorescein antracene and azlactone derivatives. The synthetic routes and purification methods of the selected compounds were discussed. The starting materials have been synthesized and then fluorescein, antracene and azlactone derivatives have been prepared. The selected derivative of fluorescein was methyl ether-ester, the fluorescein free acid was reacted with diazomethane. 9,10-Diaryl anthracene derivatives were prepared by the addition to carbonyl groups of 2-methyl anthraquinon with grignard reactives. The azlacton derivatives were formed by the condensation of the appropriate aromatic aldehydes with o-toluyl glisine and benzoyl glisine and then cyclization reaction was made. The structure of all molecules, which were synthesized was identified by their UV, mass, IR and NMR spectra. The yield, boiling and melting points and spectroscopic data were also determined and analyzed for these molecules. The compounds which were synthesized have been widely examined by134 1H and 1^C NMR spectroscopy. Also, the absorption and emission spectra have taken and their luminescence activities have been investigated. As seen the molecular structures of fluorescein and anthracene derivatives, ortho substituted aryl groups on these compound are expected to have restricted rotation around bond of attachement. Thus the rotational enantiomers of these compounds are expected to be detected in NMR spectroscopy due to magnetic non-equivalence of isotopic proton and carbon nuclei. The resolution of some of these isomers may become possible in chiral chromatography. This subject has been succeeded on fluorescein methyl- ether-ester. The *H NMR and **C NMR spectra of fluorescein methylether-ester have been detected the isomeric signals arising from the internal hindered rotation about the Cg-Cj bond. In this molecule, the Cg-Cj bond rotational axis have been served as an asymetric center and formed enantiomeric rot mers as a result of 180° rotation. The isomers have been separated on T.A.C. column. Then by using UV detector and polarimetric detector have been detected the isomeric peaks. The emission spectrum of this compound has been taken in different temperatures in relation to emission intensity. The same studies with NMR spectroscopy have been made on 2-methyl-9,10-diaryl anthracene and azlactone derivatives. But the isomeric signals of these compoundswere not seen in *H NMR or TC NMR spectra. So, in this study, the conformational isomers of restricted rotation about appropriate single bond were not detected at room temperature. A low temperature study is expected to show restricted rotational isomers. The emission spectra of azlactone derivatives has been studied and discussed for the substituent effects on emission intensities in derivatives.
133 SUMMARY The structures of condensed aromatic systems are known very well for their formation of electron donor-acceptor (EDA) charge transfer complexes. The chiral condensed aromatic systems and chiral recognation of some EDA complexes of heteroaromatics and investigation of streoisomeric forms by *H and "C NMR spectroscopy and by chiral chromatography techniques have been widely studied by Mannschreck and his groups. Some of the condensed aromatic ring systems are known to exert luminescence. Thus in this project some chiral condensed aromatic ring systems have been synthesized. Heterocyclic selected compounds with high luminescence behaviour were fluorescein antracene and azlactone derivatives. The synthetic routes and purification methods of the selected compounds were discussed. The starting materials have been synthesized and then fluorescein, antracene and azlactone derivatives have been prepared. The selected derivative of fluorescein was methyl ether-ester, the fluorescein free acid was reacted with diazomethane. 9,10-Diaryl anthracene derivatives were prepared by the addition to carbonyl groups of 2-methyl anthraquinon with grignard reactives. The azlacton derivatives were formed by the condensation of the appropriate aromatic aldehydes with o-toluyl glisine and benzoyl glisine and then cyclization reaction was made. The structure of all molecules, which were synthesized was identified by their UV, mass, IR and NMR spectra. The yield, boiling and melting points and spectroscopic data were also determined and analyzed for these molecules. The compounds which were synthesized have been widely examined by134 1H and 1^C NMR spectroscopy. Also, the absorption and emission spectra have taken and their luminescence activities have been investigated. As seen the molecular structures of fluorescein and anthracene derivatives, ortho substituted aryl groups on these compound are expected to have restricted rotation around bond of attachement. Thus the rotational enantiomers of these compounds are expected to be detected in NMR spectroscopy due to magnetic non-equivalence of isotopic proton and carbon nuclei. The resolution of some of these isomers may become possible in chiral chromatography. This subject has been succeeded on fluorescein methyl- ether-ester. The *H NMR and **C NMR spectra of fluorescein methylether-ester have been detected the isomeric signals arising from the internal hindered rotation about the Cg-Cj bond. In this molecule, the Cg-Cj bond rotational axis have been served as an asymetric center and formed enantiomeric rot mers as a result of 180° rotation. The isomers have been separated on T.A.C. column. Then by using UV detector and polarimetric detector have been detected the isomeric peaks. The emission spectrum of this compound has been taken in different temperatures in relation to emission intensity. The same studies with NMR spectroscopy have been made on 2-methyl-9,10-diaryl anthracene and azlactone derivatives. But the isomeric signals of these compoundswere not seen in *H NMR or TC NMR spectra. So, in this study, the conformational isomers of restricted rotation about appropriate single bond were not detected at room temperature. A low temperature study is expected to show restricted rotational isomers. The emission spectra of azlactone derivatives has been studied and discussed for the substituent effects on emission intensities in derivatives.
Açıklama
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Anahtar Kelimeler
Kimya, Chemistry, Antrasen, Anthracene, Azlakton, Azlacton, Floresan, Fluorescence, Organik bileşikler, Organic compounds, Saflaştırma, Purification, Spektroskopi, Spectroscopy
