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Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds

Yıl 2018, Cilt: 20 Sayı: 2, 124 - 134, 01.12.2018
https://doi.org/10.25092/baunfbed.423270

Öz

In this study novel
fluorescence active, two triazine based thiazole derivatives,  (2R,2'R)-2,4,6-triamine-N2-[2-(4-benzothiazolyl)phenyl]-N4,N6-[di(butan-1-ol)]-1,3,5-triazine
and (1S,1'S,2R,2'R)-2,4,6-triamine-N2-[2-(4-benzothiazolyl)phenyl]-N4,N6-[di(1,2-diphenylethanol)]-1,3,5-triazine
with chiral aminoalcohol groups were synthesized conveniently. Their
enantiomeric recognition abilities toward the enantiomers of carboxylic acids
such as mandelic acid and 2-chloromandelic acid were examined in DMSO/H2O
(30:70) system using fluorescence spectroscopy. It was observed that DMSO
solutions of chiral selectors showed no fluorescence emission while the
emission increased 38 and 43 fold in 95% H2O for butan-1-ol and
diphenylethanol derivatives, respectively similar with the aggregation-induced
emission (AIE) characterized compounds. In the light of the experiment results,
it was determined that the R-isomers of carboxylic acids formed more favourable
complexes with the chiral selectors when compared to S-isomers.

Kaynakça

  • Dong, J., Zhou, Y., Zhang, F. and Cui, Y., A Highly Fluorescent Metallosalalen-Based Chiral Cage for Enantioselective Recognition and Sensing, Chemistry A European Journal, 20, 6455-6461, (2014).
  • Zhao, C., Ouyang, K., Zhang, J. and Yang, N., Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion, Polymer, 93, 9-13, (2016).
  • Ghosh, K. and Majumdar, A., Isomeric chiral pyrrole diamides and their efficacy in enantioselective sensing of tartrate in sol-gel medium, Tetrahedron Letters, 57, 3629-3634, (2016).
  • Ikai, T., Yun, C., Kojima, Y., Suzuki, D., Maeda, K. and Kanoh, S., Development of Amylose- and -Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants, Molecules, 21, 1518-1529, (2016).
  • Seifert, H.M., Jiang, Y.-B. and Anslyn, E.V., Exploitation of the majority rules effect for the accurate measurement of high enantiomeric excess values using CD spectroscopy, Chemical Communications, 50, 15330-15332, (2014).
  • Wolf, C., Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods, Chemical Society Reviews, 34, 595-608, (2005).
  • Khose, V.N., John, M.E., Pandey, A.D., Borovkov, V. and Karnik, A.V., Chiral Heterocycle-Based Receptors for Enantioselective Recognition, Symmetry, 10, 34-108, (2018).
  • Bozkurt, S., Turkmen, M.B. and Soykan, C., Synthesis of new chiral calix[4]arene thiourea derivatives for enantiomeric recognition of carboxylate anions, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 84, 35-41, (2016).
  • Fu, Z.-H., Yan, L.-B., Zhang, X., Zhu, F.-F., Han, X.-L., Fang, J., Wang, Y.-W. and Peng, Y., A fluorescein-based chemosensor for relay fluorescence recognition of Cu(II) ions and biothiols in water and its applications to molecular logic gate and living cell imaging, Organic  Biomolecular Chemistry, 15, 4115-4121, (2017).
  • Pal, D., Moczar, I., Kormos, A., Baranyai, P. and Huszthy, P., Synthesis and enantiomeric recognition studies of optically active 5,5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives, Tetrahedron: Asymmetry, 27, 918-922, (2016).
  • Heo, J. and Mirkin, C.A., Pseudo-allosteric recognition of mandelic acid with an enantioselective coordination complex, Angewandte Chemie, International Edition, 45, 941-944, (2006).
  • Huang, H., Yang, W. and Deng, J., Chiral, fluorescent microparticles constructed by optically active helical substituted polyacetylene: preparation and enantioselective recognition ability, RSC Advances, 5, 26236-26245, (2015).
  • Wang, C., Wu, E., Wu, X., Xu, X., Zhang, G. and Pu, L., Enantioselective fluorescent recognition in the fluorous phase: enhanced reactivity and expanded chiral recognition, Journal of the American Chemical Society, 137, 3747-3750, (2015).
  • Bozkurt, S. and Türkmen, M.B., New chiral oxo-bridged calix[2]arene[2]triazine for the enantiomeric recognition of -racemic carboxylic acids, Tetrahedron: Asymmetry, 27, 443-447, (2016).
  • Li, G., Cao, J., Zong, W., Lei, X. and Tan, R., Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents, Organic Chemistry Frontiers, 3, 96-102, (2016).
  • Ikai, T., Suzuki, D., Kojima, Y., Yun, C., Maeda, K. and Kanoh, S., Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants, Polymer Chemistry, 7, 4793-4801, (2016).
  • Pu, L., Fluorescence of organic molecules in chiral recognition, Chemical Reviews, 104, 1687-1716, (2004).
  • Ooyama, Y., Sugino, M., Enoki, T., Yamamoto, K., Tsunoji, N. and Ohshita, J., Aggregation-induced emission (AIE) characteristic of water-soluble tetraphenylethene (TPE) bearing four sulfonate salts, New Journal of Chemistry, 41, 4747-4749, (2017).
  • Xiong, J.-B., Xie, W.-Z., Sun, J.-P., Wang, J.-H., Zhu, Z.-H., Feng, H.-T., Guo, D., Zhang, H. and Zheng, Y.-S., Enantioselective recognition for many different kinds of chiral guests by one chiral receptor based on tetraphenylethylene cyclohexylbisurea, Journal of Organic Chemistry, 81, 3720-3726, (2016).
  • Xu, K.-X., Jiao, S.-Y., Yao, W.-Y., Kong, H.-J., Zhang, J.-L. and Wang, C.-J., Syntheses and highly enantioselective fluorescent recognition of -hydroxyl/amino carboxylic acid anions in protic solutions, Sensors and Actuators B: Chemical, 177, 384-389, (2013).
  • Ghosh, K. and Sarkar, T., Anthracene-labeled pyridinium-based symmetrical chiral chemosensor for enantioselective recognition of L-tartrate, Tetrahedron Letters, 55, 1342-1346, (2014).
  • Halay, E. and Bozkurt ,S., Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles, Chirality, 30, 275-283, (2018).
  • Shi, H., Zhang, X., Gui, C., Wang, S., Fang, L., Zhao, Z., Chen, S. and Tang, B.Z., Synthesis, aggregation-induced emission and electroluminescence properties of three new phenylethylene derivatives comprising carbazole and (dimesitylboranyl)phenyl groups, Journal of Materials Chemistry C, 5, 11741-11750, (2017).
  • Zhang, H., Li, H., Wang, J., Sun, J., Qin, A. and Tang, B.Z., Axial chiral aggregation-induced emission luminogens with aggregation-annihilated circular dichroism effect, Journal of Materials Chemistry C, 3, 5162-5166, (2015).
  • Feng, H.-T., Zhang, X. and Zheng, Y.-S., Fluorescence turn-on enantioselective recognition of both chiral acidic compounds and -amino acids by a chiral tetraphenylethylene macrocycle amine, Journal of Organic Chemistry, 80, 8096-8101, (2015).

Triazin bazlı kiral floresans bileşiklerin sentezi ve enantiyomerik tanınma çalışmaları

Yıl 2018, Cilt: 20 Sayı: 2, 124 - 134, 01.12.2018
https://doi.org/10.25092/baunfbed.423270

Öz

Bu çalışmada yeni floresans aktif, iki adet triazin bazlı tiyazol
türevleri, (2R,2'R)-2,4,6-triamin-N2-[2-(4-benzotiyazolil)fenil]-N4,N6-[di(bütan-1-ol)]-1,3,5-triazin
ve (1S,1'S, 2R,2'R)-2,4,6-triamin-N2-[2-(4-benzotiyazolil)fenil]-N4,N6-[di(1,2-difenil
etanol)]-1,3,5-triazin uygun şekilde sentezlendi. İlgili bileşiklerin, mandelik
asit ve 2-kloromandelik asit gibi karboksilik asit enantiyomerlerine karşı
enantiyomerik tanıma yetenekleri, DMSO/H2O (30:70) sisteminde
floresans spektroskopisi aracılığıyla incelendi. Kiral seçicilerin DMSO
çözeltileri floresans emisyonu göstermez iken, %95 su yüzdesine çıkıldığında,
agregasyona bağlı emisyon karakterli bileşiklere benzer olarak emisyonun
sırasıyla bütan-1-ol ve difeniletanol türevleri için 38 ve 43 kat arttığı
gözlemlendi. Deney sonuçları ışığında, karboksilik asitlerin R-izomerlerinin,
S-izomerleri ile karşılaştırıldığında kiral seçiciler ile daha uygun
kompleksler oluşturduğu saptandı. 

Kaynakça

  • Dong, J., Zhou, Y., Zhang, F. and Cui, Y., A Highly Fluorescent Metallosalalen-Based Chiral Cage for Enantioselective Recognition and Sensing, Chemistry A European Journal, 20, 6455-6461, (2014).
  • Zhao, C., Ouyang, K., Zhang, J. and Yang, N., Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion, Polymer, 93, 9-13, (2016).
  • Ghosh, K. and Majumdar, A., Isomeric chiral pyrrole diamides and their efficacy in enantioselective sensing of tartrate in sol-gel medium, Tetrahedron Letters, 57, 3629-3634, (2016).
  • Ikai, T., Yun, C., Kojima, Y., Suzuki, D., Maeda, K. and Kanoh, S., Development of Amylose- and -Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants, Molecules, 21, 1518-1529, (2016).
  • Seifert, H.M., Jiang, Y.-B. and Anslyn, E.V., Exploitation of the majority rules effect for the accurate measurement of high enantiomeric excess values using CD spectroscopy, Chemical Communications, 50, 15330-15332, (2014).
  • Wolf, C., Stereolabile chiral compounds: analysis by dynamic chromatography and stopped-flow methods, Chemical Society Reviews, 34, 595-608, (2005).
  • Khose, V.N., John, M.E., Pandey, A.D., Borovkov, V. and Karnik, A.V., Chiral Heterocycle-Based Receptors for Enantioselective Recognition, Symmetry, 10, 34-108, (2018).
  • Bozkurt, S., Turkmen, M.B. and Soykan, C., Synthesis of new chiral calix[4]arene thiourea derivatives for enantiomeric recognition of carboxylate anions, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 84, 35-41, (2016).
  • Fu, Z.-H., Yan, L.-B., Zhang, X., Zhu, F.-F., Han, X.-L., Fang, J., Wang, Y.-W. and Peng, Y., A fluorescein-based chemosensor for relay fluorescence recognition of Cu(II) ions and biothiols in water and its applications to molecular logic gate and living cell imaging, Organic  Biomolecular Chemistry, 15, 4115-4121, (2017).
  • Pal, D., Moczar, I., Kormos, A., Baranyai, P. and Huszthy, P., Synthesis and enantiomeric recognition studies of optically active 5,5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives, Tetrahedron: Asymmetry, 27, 918-922, (2016).
  • Heo, J. and Mirkin, C.A., Pseudo-allosteric recognition of mandelic acid with an enantioselective coordination complex, Angewandte Chemie, International Edition, 45, 941-944, (2006).
  • Huang, H., Yang, W. and Deng, J., Chiral, fluorescent microparticles constructed by optically active helical substituted polyacetylene: preparation and enantioselective recognition ability, RSC Advances, 5, 26236-26245, (2015).
  • Wang, C., Wu, E., Wu, X., Xu, X., Zhang, G. and Pu, L., Enantioselective fluorescent recognition in the fluorous phase: enhanced reactivity and expanded chiral recognition, Journal of the American Chemical Society, 137, 3747-3750, (2015).
  • Bozkurt, S. and Türkmen, M.B., New chiral oxo-bridged calix[2]arene[2]triazine for the enantiomeric recognition of -racemic carboxylic acids, Tetrahedron: Asymmetry, 27, 443-447, (2016).
  • Li, G., Cao, J., Zong, W., Lei, X. and Tan, R., Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents, Organic Chemistry Frontiers, 3, 96-102, (2016).
  • Ikai, T., Suzuki, D., Kojima, Y., Yun, C., Maeda, K. and Kanoh, S., Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants, Polymer Chemistry, 7, 4793-4801, (2016).
  • Pu, L., Fluorescence of organic molecules in chiral recognition, Chemical Reviews, 104, 1687-1716, (2004).
  • Ooyama, Y., Sugino, M., Enoki, T., Yamamoto, K., Tsunoji, N. and Ohshita, J., Aggregation-induced emission (AIE) characteristic of water-soluble tetraphenylethene (TPE) bearing four sulfonate salts, New Journal of Chemistry, 41, 4747-4749, (2017).
  • Xiong, J.-B., Xie, W.-Z., Sun, J.-P., Wang, J.-H., Zhu, Z.-H., Feng, H.-T., Guo, D., Zhang, H. and Zheng, Y.-S., Enantioselective recognition for many different kinds of chiral guests by one chiral receptor based on tetraphenylethylene cyclohexylbisurea, Journal of Organic Chemistry, 81, 3720-3726, (2016).
  • Xu, K.-X., Jiao, S.-Y., Yao, W.-Y., Kong, H.-J., Zhang, J.-L. and Wang, C.-J., Syntheses and highly enantioselective fluorescent recognition of -hydroxyl/amino carboxylic acid anions in protic solutions, Sensors and Actuators B: Chemical, 177, 384-389, (2013).
  • Ghosh, K. and Sarkar, T., Anthracene-labeled pyridinium-based symmetrical chiral chemosensor for enantioselective recognition of L-tartrate, Tetrahedron Letters, 55, 1342-1346, (2014).
  • Halay, E. and Bozkurt ,S., Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles, Chirality, 30, 275-283, (2018).
  • Shi, H., Zhang, X., Gui, C., Wang, S., Fang, L., Zhao, Z., Chen, S. and Tang, B.Z., Synthesis, aggregation-induced emission and electroluminescence properties of three new phenylethylene derivatives comprising carbazole and (dimesitylboranyl)phenyl groups, Journal of Materials Chemistry C, 5, 11741-11750, (2017).
  • Zhang, H., Li, H., Wang, J., Sun, J., Qin, A. and Tang, B.Z., Axial chiral aggregation-induced emission luminogens with aggregation-annihilated circular dichroism effect, Journal of Materials Chemistry C, 3, 5162-5166, (2015).
  • Feng, H.-T., Zhang, X. and Zheng, Y.-S., Fluorescence turn-on enantioselective recognition of both chiral acidic compounds and -amino acids by a chiral tetraphenylethylene macrocycle amine, Journal of Organic Chemistry, 80, 8096-8101, (2015).
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Erkan Halay

Selahattin Bozkurt

Yayımlanma Tarihi 1 Aralık 2018
Gönderilme Tarihi 30 Mart 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 20 Sayı: 2

Kaynak Göster

APA Halay, E., & Bozkurt, S. (2018). Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 20(2), 124-134. https://doi.org/10.25092/baunfbed.423270
AMA Halay E, Bozkurt S. Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds. BAUN Fen. Bil. Enst. Dergisi. Aralık 2018;20(2):124-134. doi:10.25092/baunfbed.423270
Chicago Halay, Erkan, ve Selahattin Bozkurt. “Synthesis and Enantiomeric Recognition Studies of Triazine-Based Chiral Fluorescent Compounds”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 20, sy. 2 (Aralık 2018): 124-34. https://doi.org/10.25092/baunfbed.423270.
EndNote Halay E, Bozkurt S (01 Aralık 2018) Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 20 2 124–134.
IEEE E. Halay ve S. Bozkurt, “Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds”, BAUN Fen. Bil. Enst. Dergisi, c. 20, sy. 2, ss. 124–134, 2018, doi: 10.25092/baunfbed.423270.
ISNAD Halay, Erkan - Bozkurt, Selahattin. “Synthesis and Enantiomeric Recognition Studies of Triazine-Based Chiral Fluorescent Compounds”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 20/2 (Aralık 2018), 124-134. https://doi.org/10.25092/baunfbed.423270.
JAMA Halay E, Bozkurt S. Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds. BAUN Fen. Bil. Enst. Dergisi. 2018;20:124–134.
MLA Halay, Erkan ve Selahattin Bozkurt. “Synthesis and Enantiomeric Recognition Studies of Triazine-Based Chiral Fluorescent Compounds”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 20, sy. 2, 2018, ss. 124-3, doi:10.25092/baunfbed.423270.
Vancouver Halay E, Bozkurt S. Synthesis and enantiomeric recognition studies of triazine-based chiral fluorescent compounds. BAUN Fen. Bil. Enst. Dergisi. 2018;20(2):124-3.