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NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ

Yıl 2019, Cilt: 7 Sayı: 4, 742 - 748, 04.12.2019
https://doi.org/10.36306/konjes.654899

Öz

Naftalin-bağlı makro halkalı ligant (E)-N-(naftalin-9-ilmetilen)-2-(1,4,7,10-tetraazabisiklo[8.2.2] tetradekan-4-il)-etanamin (4) ve Cu(II), Ni (II), Zn (II) komplekslerinin sentez ve karakterizasyonları yapılmıştır. Schiff bazı kondenzasyon reaksiyonuyla elde edilen (E)-N-(naftalin-9-ilmetilen)-2-bromoetanamin (2) molekülü ve glioksal-köprülü tetraaza molekülünün reaksiyona tabi tutulmasıyla monokuaterner amonyum tuzu (3) elde edilmiştir. Daha sonra indirgenme reaksiyonu ile (E)-N-(naftalin-9-ilmetilen)-2-(1,4,7,10-tetraazabisiklo[8.2.2]tetradekan-4-il)-etanamin (4)makro halkalı ligantın sentezi tamamlanmıştır. Geçiş metal iyonlarına karşı seçici duyarlılığa sahip olması için konformasyonel olarak kısıtlandırılmış olan bu makro halkalı liganta (1,4,7,10-tetraazasiklododekan) floresans özellikteki naftalin bağlanmıştır. Bu makro halkalı ligantın ve komplekslerinin floresans özellikleri araştırılmıştır. Bulunan sonuçlara göre bu ligantın Zn(II) iyonlarına karşı seçici özellikte olduğu bulunmuştur.

Kaynakça

  • Abdulwahaab,B.H., Burke,B.P., Domarkas, J.,Silversides,J.D., Prior,T.J., Archibald,S.J., 2016, “Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry”, J. Org. Chem., Cilt 81, ss. 890−898.
  • Amorim, M.T.S., Chaves, S., Delgado, R., de Silva, J.J.R.F., 1991, “Oxatriaza macrocyclicligants:studies of protonation and metal complexation”, Dalton Trans., Cilt 11, ss., 3065–3072.
  • Aoki, S., Zulkefeli, M., Shiro, M., Kohsako, M., Takeda, K., Kimura, E., 2005, “ALuminescence Sensorof Inositol 1,4,5-Triphosphate and Its Model Compound by Ruthenium-Templated Assembly ofa Bis(Zn2+-Cyclen) Complex Having a 2,2”-Bipyridyl Linker (Cyclen=1,4,7,10-Tetraazacyclododecane)”, J. Am. Chem. Soc., Cilt 127, ss. 9129–9139.
  • Aoki, S., Kagata, D., Shiro, M., Takeda, K., Kimura, E., 2004, “Metal Chelation-Controlled TwistedIntramolecular Charge Transfer and Its Application to Fluorescent Sensing ofMetal Ions andAnions”, J. Am. Chem. Soc., Cilt 126, ss. 13377–13390.
  • Aoki, S., Sakurama, K., Ohshima, R., Matsuo, N., Yamada, Y., Takasawa, R., Tanuma, S., Takeda, K.,Kimura, 2008, “Design and synthesis of a caged Zn2+ probe, 8-benzenes-sulphonyloxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant1,4,7,10-tetraazacyclododecane, and itshydrolytic uncaging upon complexation with Zn2+”, E., Inorg. Chem., Cilt 47, ss. 2747–2754.
  • de Silva, A.P., Gunaratne, H.Q., McCoy, C.P., 1996, “Direct visual indication of pHwindows: “off–on–off” fluorescent PET (photoinduced electron transfer) sensors/switches”, Chem. Commun., ss. 2399.
  • Fabbrizzi, L., Licchelli, M., Pallavicini, P., Parodi, L., 1998, “Controllable IntramolecularMotions ThatGenerate Fluorescent Signals for a Metal Scorpionate Complex”, Angew.Chem. Int. Ed., Cilt 37, ss. 800.
  • Gunnlaugsson, T., Davis, A.P., Glynn, M., 2001, “Fluorescent photoinduced electron transfer(PET)sensing of anions using charge neutral chemosensors”, Chem. Commun., ss.2556.
  • Huang, Zheng, Liu, Yan-Hong, Zhang, Yi-Mei, Zhang Ji, Liu, Qiang, Yu, Xiao-Qi, 2015, “Cyclen-based cationic lipids containing a pH-sensitive moiety as gene delivery vectors”, Org. Biomol. Chem. Cilt 13, ss. 620-630.
  • Koike, T., Watanabe, T., Aoki, S., Kimura, E., Shiro, M., 1996, “A Novel BiomimeticZinc(II)−Fluorophore, Dansylamidoethyl−Pendant Macrocyclic Tetraamine 1,4,7,10-Tetraazacyclododecane (Cyclen)”, J. Am. Chem. Soc., Cilt 118, ss. 2696–2703.
  • Obalı, A.Y., Uçan, H.İ., 2012, “Aromatic Chromophore-Tethered Schiff Base Ligands and Their Iron(III)/Chromium(III) Salen and Saloph Capped Complexes”, Journal of Fluorescence, Cilt 22, ss.1357-1370.
  • Obalı, A.Y., Uçan, H.İ., 2015, “Novel dipodal Schiff base compounds: Synthesis, characterization and spectroscopic studies”, Journal of Molecular Structure, Cilt 1081, ss. 74-78.
  • Le Baccon, M., Chuburu, F., Toupet, L., Handel, H., Soibinet, M., Dechamps-Olivier, I., Barbier, J.P., Aplincourt, M.,2001, “Bis-aminals: efficient tools for bis-macrocycle synthesis”, New J. Chem., Cilt 25, ss. 1168.
  • Shiraishi Y., Sumiya S., Kohno Y., and Hirai T., 2008, “A Rhodamine−Cyclen Conjugate as aHighlySensitive and Selective Fluorescent Chemosensor for Hg(II)”, J. Org. Chem., Cilt 73, ss. 8571–8574.
  • Weisman, G.R., Ho,S.C.H. and Johnson, V., 1980, “Tetracyclic Tetraamines by Glyoxal-Macrocyclic Tetraamine Condensation”, Tetrahedron Lett., Cilt 21, ss. 335.

Synthesis of Naphthalene-Bonded Macrocyclic Complexes And Investigation Of Spectroscopic Behaviours

Yıl 2019, Cilt: 7 Sayı: 4, 742 - 748, 04.12.2019
https://doi.org/10.36306/konjes.654899

Öz

Synthesis and characterizations of naphthalene-bonded macrocyclic ligand (E)-N-(naphthalene-9-ylmethylene)-2-(1,4,7,10-tetraazabicyclo[8.2.2]tetradecan-4-yl)-ethanamine (4)and Cu(II), Ni (II), Zn (II) complexes were performed. By the reaction of (E)-N-(naphthalene-9-ylmethylene)-2-bromoethylamine (2), which was obtained by the Schiff base condensation reaction, and the glyoxal-bridged tetraaza molecule, the monoquaternary ammonium salt (3) was obtained. The synthesis of (E)-N-(naphthalene-9-ylmethylene)-2-(1,4,7,10-tetraazabicyclo[8.2.2]tetradecan-4-yl)-ethanamine (4) macrocyclic ligand was then completed by the reduction reaction. Fluorescence naphthalene group was bonded to this conformationally constrained macrocyclic ligand (1,4,7,10-tetraazacyclododecane) because of getting selectivity towards transition metal ions. The fluorescence properties of this macro cyclic ligand and its complexes were investigated. According to the results, it was found that this ligand was selective towards Zn (II) ions.

Kaynakça

  • Abdulwahaab,B.H., Burke,B.P., Domarkas, J.,Silversides,J.D., Prior,T.J., Archibald,S.J., 2016, “Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry”, J. Org. Chem., Cilt 81, ss. 890−898.
  • Amorim, M.T.S., Chaves, S., Delgado, R., de Silva, J.J.R.F., 1991, “Oxatriaza macrocyclicligants:studies of protonation and metal complexation”, Dalton Trans., Cilt 11, ss., 3065–3072.
  • Aoki, S., Zulkefeli, M., Shiro, M., Kohsako, M., Takeda, K., Kimura, E., 2005, “ALuminescence Sensorof Inositol 1,4,5-Triphosphate and Its Model Compound by Ruthenium-Templated Assembly ofa Bis(Zn2+-Cyclen) Complex Having a 2,2”-Bipyridyl Linker (Cyclen=1,4,7,10-Tetraazacyclododecane)”, J. Am. Chem. Soc., Cilt 127, ss. 9129–9139.
  • Aoki, S., Kagata, D., Shiro, M., Takeda, K., Kimura, E., 2004, “Metal Chelation-Controlled TwistedIntramolecular Charge Transfer and Its Application to Fluorescent Sensing ofMetal Ions andAnions”, J. Am. Chem. Soc., Cilt 126, ss. 13377–13390.
  • Aoki, S., Sakurama, K., Ohshima, R., Matsuo, N., Yamada, Y., Takasawa, R., Tanuma, S., Takeda, K.,Kimura, 2008, “Design and synthesis of a caged Zn2+ probe, 8-benzenes-sulphonyloxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant1,4,7,10-tetraazacyclododecane, and itshydrolytic uncaging upon complexation with Zn2+”, E., Inorg. Chem., Cilt 47, ss. 2747–2754.
  • de Silva, A.P., Gunaratne, H.Q., McCoy, C.P., 1996, “Direct visual indication of pHwindows: “off–on–off” fluorescent PET (photoinduced electron transfer) sensors/switches”, Chem. Commun., ss. 2399.
  • Fabbrizzi, L., Licchelli, M., Pallavicini, P., Parodi, L., 1998, “Controllable IntramolecularMotions ThatGenerate Fluorescent Signals for a Metal Scorpionate Complex”, Angew.Chem. Int. Ed., Cilt 37, ss. 800.
  • Gunnlaugsson, T., Davis, A.P., Glynn, M., 2001, “Fluorescent photoinduced electron transfer(PET)sensing of anions using charge neutral chemosensors”, Chem. Commun., ss.2556.
  • Huang, Zheng, Liu, Yan-Hong, Zhang, Yi-Mei, Zhang Ji, Liu, Qiang, Yu, Xiao-Qi, 2015, “Cyclen-based cationic lipids containing a pH-sensitive moiety as gene delivery vectors”, Org. Biomol. Chem. Cilt 13, ss. 620-630.
  • Koike, T., Watanabe, T., Aoki, S., Kimura, E., Shiro, M., 1996, “A Novel BiomimeticZinc(II)−Fluorophore, Dansylamidoethyl−Pendant Macrocyclic Tetraamine 1,4,7,10-Tetraazacyclododecane (Cyclen)”, J. Am. Chem. Soc., Cilt 118, ss. 2696–2703.
  • Obalı, A.Y., Uçan, H.İ., 2012, “Aromatic Chromophore-Tethered Schiff Base Ligands and Their Iron(III)/Chromium(III) Salen and Saloph Capped Complexes”, Journal of Fluorescence, Cilt 22, ss.1357-1370.
  • Obalı, A.Y., Uçan, H.İ., 2015, “Novel dipodal Schiff base compounds: Synthesis, characterization and spectroscopic studies”, Journal of Molecular Structure, Cilt 1081, ss. 74-78.
  • Le Baccon, M., Chuburu, F., Toupet, L., Handel, H., Soibinet, M., Dechamps-Olivier, I., Barbier, J.P., Aplincourt, M.,2001, “Bis-aminals: efficient tools for bis-macrocycle synthesis”, New J. Chem., Cilt 25, ss. 1168.
  • Shiraishi Y., Sumiya S., Kohno Y., and Hirai T., 2008, “A Rhodamine−Cyclen Conjugate as aHighlySensitive and Selective Fluorescent Chemosensor for Hg(II)”, J. Org. Chem., Cilt 73, ss. 8571–8574.
  • Weisman, G.R., Ho,S.C.H. and Johnson, V., 1980, “Tetracyclic Tetraamines by Glyoxal-Macrocyclic Tetraamine Condensation”, Tetrahedron Lett., Cilt 21, ss. 335.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Aslıhan YILMAZ OBALI Bu kişi benim
SELÇUK ÜNİVERSİTESİ, FEN FAKÜLTESİ
Türkiye

Yayımlanma Tarihi 4 Aralık 2019
Yayınlandığı Sayı Yıl 2019 Cilt: 7 Sayı: 4

Kaynak Göster

Bibtex @araştırma makalesi { konjes654899, journal = {Konya Journal of Engineering Sciences}, eissn = {2667-8055}, address = {Konya Teknik Üniversitesi Mühendislik ve Doğa Bilimleri Fakültesi Dekanlığı, Alaeddin Keykubat Yerleşkesi, Akademi Mah. Yeni İstanbul Cad. No:369 Posta Kodu:42130 Selçuklu-Konya / TÜRKİYE}, publisher = {Konya Teknik Üniversitesi}, year = {2019}, volume = {7}, number = {4}, pages = {742 - 748}, doi = {10.36306/konjes.654899}, title = {NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ}, key = {cite}, author = {Yılmaz Obalı, Aslıhan} }
APA Yılmaz Obalı, A. (2019). NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ . Konya Journal of Engineering Sciences , 7 (4) , 742-748 . DOI: 10.36306/konjes.654899
MLA Yılmaz Obalı, A. "NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ" . Konya Journal of Engineering Sciences 7 (2019 ): 742-748 <https://dergipark.org.tr/tr/pub/konjes/issue/50455/654899>
Chicago Yılmaz Obalı, A. "NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ". Konya Journal of Engineering Sciences 7 (2019 ): 742-748
RIS TY - JOUR T1 - NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ AU - AslıhanYılmaz Obalı Y1 - 2019 PY - 2019 N1 - doi: 10.36306/konjes.654899 DO - 10.36306/konjes.654899 T2 - Konya Journal of Engineering Sciences JF - Journal JO - JOR SP - 742 EP - 748 VL - 7 IS - 4 SN - -2667-8055 M3 - doi: 10.36306/konjes.654899 UR - https://doi.org/10.36306/konjes.654899 Y2 - 2019 ER -
EndNote %0 Konya Mühendislik Bilimleri Dergisi NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ %A Aslıhan Yılmaz Obalı %T NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ %D 2019 %J Konya Journal of Engineering Sciences %P -2667-8055 %V 7 %N 4 %R doi: 10.36306/konjes.654899 %U 10.36306/konjes.654899
ISNAD Yılmaz Obalı, Aslıhan . "NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ". Konya Journal of Engineering Sciences 7 / 4 (Aralık 2019): 742-748 . https://doi.org/10.36306/konjes.654899
AMA Yılmaz Obalı A. NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ. KONJES. 2019; 7(4): 742-748.
Vancouver Yılmaz Obalı A. NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ. Konya Journal of Engineering Sciences. 2019; 7(4): 742-748.
IEEE A. Yılmaz Obalı , "NAFTALİN-BAĞLI MAKROHALKALI KOMPLEKSLERİN SENTEZİ VE SPEKTROSKOPİK DAVRANIŞLARININ İNCELENMESİ", Konya Journal of Engineering Sciences, c. 7, sayı. 4, ss. 742-748, Ara. 2019, doi:10.36306/konjes.654899