Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles


HALAY E., BOZKURT S.

Chirality, cilt.30, sa.3, ss.275-283, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 30 Sayı: 3
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/chir.22792
  • Dergi Adı: Chirality
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.275-283
  • Anahtar Kelimeler: aggregation-induced emission, chiral recognition, chiral thiazole derivatives, fluorescence spectroscopy, hydrogen bonding, triazine
  • Uşak Üniversitesi Adresli: Evet

Özet

Hydrogen bonding and π-π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such information, triazine-based chiral, fluorescence active novel thiazole derivatives L1 and L2 were designed and synthesized from (S)-(−)-2-amino-1-butanol and (1S,2R)-(+)-2-amino-1,2-diphenylethanol. The structural establishment of these compounds was made by spectroscopic methods such as FTIR, 1H, and 13C NMR. While the solution of these compounds in DMSO did not show any fluorescence emission, it was observed that the emission increased 44-fold for L1 and 55-fold for L2 in 95% water, similar to the aggregation-induced emission (AIE) characterized compounds. In this regard, enantioselective capabilities of these compounds against carboxylic acids were tested, and in experiments carried out at a ratio of 40/60 DMSO/H2O, it was determined that R-2ClMA increased the fluorescence emission of L1 chiral receptor by 2.59 times compared to S-isomer.