An efficient novel acetate anion receptor based on isatin

Abstract

Um receptor para reconhecimento de ânions derivado da tiouréia foi sintetizado combinandose indolina-2,3-diona e 1,3-diaminotiouréia. A interação pode ser facilmente monitorada acompanhando-se as mudanças no espectro de absorção na região do UV-vis induzidas pela complexação de um dado ânion. Por exemplo, verificou-se que o fluoreto liga-se ao receptor na proporção de 1:2, mas esta muda para 1:1 no caso dos ânions di-hidrogenofosfato e acetato. Este último apresenta a maior constante de afinidade dentre eles indicando um melhor reconhecimento molecular pelo novo receptor. Finalmente, a natureza da interação entre o novo receptor e o ânion acetato foram explorados utilizando-se espectroscopia de 1 H-RMN.An anion recognition receptor, a kind of thiourea derivative, was designed and synthesized by combining indoline-2,3-dione and 1,3-diaminothiourea. The anion recognition can be easily monitored by anion complexation induced changes in UV-vis absorption spectra. In particular, the binding ratio between the receptor and fluoride is 1:2 but in the case of dihydrogenphosphate and acetate are 1:1. Moreover, the affinity constants revealed that the receptor can recognize acetate well. Finally, 1 H NMR experiments were carried out to explore the nature of interaction between this new receptor and acetate.

Self‐association, tautomerism and E–Zisomerization of isatin–phenylsemicarbazones – spectral study and theoretical calculations

“…Due to the relatively strong hydrogen bond acceptor ability of –C=O and donor ability of –NH structural fragments, molecules containing a semicarbazone or urea skeleton are included in the group of compounds mentioned above. The complementarity of such molecules and the strength of their inter‐molecular hydrogen bonds often lead to the formation of associates, to their ability to interact with anions and to the formation of complexes with various metal cations . The conformational arrangement of these molecules often affects the stability of the forming associates and/or complexes, respectively.…”

Isatin‐Triazole‐Tethered, Tetrahydropyridine‐Based Chemosensors for Selective Recognition of Fe3+ Ions and Molecular Logic Gate Behavior

“…al have reported isatin pentafluorophenyl hydrazone (I) and N, N'-di-(indolino-2-one-3-yl)-1,3-diminothiourea (II) based colorimetric sensors for binding of fluoride and acetate ions. [15,16] N Gucchait et al have reported a rhodamine-isatin based fluorescent chemosensor 17 for the detection of Cr 3 + ions and A. Paramanik et al have reported the isatin based spiro compounds (III) for detection of Cu 2 + ions (Figure 1). [18,19] These reports indicate that chemosensors containing isatin scaffold are excellent candidate for detection of metal ions.…”

“…al and H. Su et. al have reported isatin pentafluorophenyl hydrazone ( I ) and N, N’‐di‐(indolino‐2‐one‐3‐yl)‐1,3‐diminothiourea ( II ) based colorimetric sensors for binding of fluoride and acetate ions [15,16] . N Gucchait et al .…”

Instantaneous and Selective Bare Eye Detection of Inorganic Fluoride Ion by Coumarin–Pyrazole‐Based Receptors

“…Our group is engaged in synthesis of biologically significant heterocyclic derivatives and scanty reports of heterocycles as selective naked eye fluoride receptors motivated us to develop a new fluoride ion receptor R1 which could provide a distinctive solution to mitigate the above said problems. Literature survey revealed that coumarin unit has been condensed with thiazole moiety to construct chromophoric units .…”