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

Year 2018, Volume: 20 Issue: 2, 124 - 134, 01.12.2018

Erkan Halay , Selahattin Bozkurt

https://doi.org/10.25092/baunfbed.423270

Abstract

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.

Keywords

Chiral recognition , fluorescence , triazine , thiazole , hydrogen bonding , carboxylic acid , aggregation-induced emission

Triazin bazlı kiral floresans bileşiklerin sentezi ve enantiyomerik tanınma çalışmaları

Abstract

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. 

Keywords

Kiral tanınma , floresans , triazin , tiyazol , hidrojen bağı , karboksilik asit , kümelenmeye dayalı emisyon

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