Colorimetric anion sensor based on receptor having indole- and thiourea-binding sites

Murali, M. G.; Vishnumurthy, KA; Seethamraju, Sindhu; Ramamurthy, Praveen C.

doi:10.1039/c4ra01555j

Cited by 20 publications

(6 citation statements)

References 49 publications

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“…56 Recognition of anions also follows through electrostatic interactions 57 and coordination through metal ions, 58 etc. Hydrogen bonding involving NH and OH functional group 59,60 provides ample stabilization in the anion recognition and complex formation. It was found that the phenolic OH ionized and formed a strong complex in many receptor/anion complexes; however, the amide NH group mostly stabilized the complex via strong H-bond formation and was less susceptible to deprotonation compared to phenolic OH group present in the receptor.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Molecular Details of Acetate Binding to a New Diamine Receptor by NMR and FT-IR Analyses

et al. 2016

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Acetate anion plays an important role in several biochemical functions such as enzyme reaction, antibody response, and action of receptor molecules. This investigation reports the synthesis and molecular details of a unique receptor, 2-amino-N-(2-amino-benzyl)-benzamide (R) that senses selectively acetate via simultaneous involvement of one aromatic amine group and an amide proton of the receptor molecule. Solution-state NMR, steady-state fluorescence, and FT-IR examinations established that the acetate anion binds to the receptor with 1:1 ratio with high specificity. The binding was stabilized by two H-bond formations between the oxygen atoms of acetate anion and two H atoms, one from amide group and the other from the amine group of the receptor. The binding interaction caused significant changes in the chemical shift of the receptor protons, and the evaluated affinity constant, from the NMR measurements, was found to be 1.87 × 10(4) M(-1). Density functional theory (DFT) analysis further showed a significant rotation of one of the two aromatic rings leading to formation of a 10-member ring involving the acetate anion, amide proton, and the one amine group attached to aromatic ring. The H-bond patterns observed in the crystal structure were significantly changed due to complex formation. However, the changes in the geometrical arrangement in the complex caused a small but significant increase of the fluorescence emission. Acetate geometry and unique positioning of the amide and amine groups of the receptor render the recognition feasible, and DFT analysis estimated ∼30 kJ M(-1) stabilization due to 1:1 complexation. Such positioning and geometrical arrangement may make the receptor very specific to bind acetate anion, and as such R became a very relevant molecule in detection and function of the acetate anion present in complex biochemical systems.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Molecular Details of Acetate Binding to a New Diamine Receptor by NMR and FT-IR Analyses

et al. 2016

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“…Three 1D and 2D cobalt complexes were obtained. Solutions of complex 2 in DMF showed obvious color variation and fluorescence enhancement induced by the presence of acetate [20][21][22]. The thermal and gas adsorption properties of complexes 1 and 3 were investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, fluorescence, and sorption properties of cobalt coordination polymers of the N,N′-bis(4-pyridylmethyl)naphthalene diimide ligand

Liao

Pan

et al. 2015

Transition Met Chem

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Three cobalt coordination polymers, namely {[Co(4-pmntd) 2 (CF 3 SO 3 )(H 2 O)]Á(CF 3 SO 3 )Á(C 2 H 5 OH)Á0.5 (HCCl 3 )ÁH 2 O} n (1), {[Co(4-pmntd)(H 2 O) 4 ]Á(NO 3 ) 2 ÁH 2 O} n(2), and {[Co(4-pmntd)(pta)(CH 3 OH) 2 ]Á2(CHCl 3 )} n (3) (4-pmntd = N,N 0 -bis(4-pyridylmethyl)-naphthalene diimide; pta = terephthalate), have been synthesized by reactions of 4-pmntd with Co(CF 3 SO 3 ) 2 Á4H 2 O, Co(NO 3 ) 2 Á6H 2 O, and Co(pta), respectively. The complexes have been characterized by elemental analyses, powder X-ray diffraction, thermogravimetric analyses, IR spectroscopy, and singlecrystal X-ray diffraction. In complex 1, the ligand adopts U-mode, resulting in a dumbbell-like 2D (4, 4)-sql net structure in a non-interpenetrating edge-to-edge arrangement. The Z-mode ligand arrangement leads to 1D zigzag chains for complex 2, and a 2D twofold interpenetrating bat-like (4, 4)-sql net for complex 3. A solution of complex 2 in DMF showed a change in color and remarkably enhanced fluorescence upon the addition of two equivalents of acetate, whereas other anions did not induce a color change. Hence, complex 2 can act as a highly promising acetate-detecting reagent. Their thermal and the gas adsorption properties of complexes 1 and 3 were investigated.

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“…For instance, anthracene, 10,11 anthraquinone, 12,13 calixpyrrole, 14,15 dipyrrolylquinoxaline, 16 and other chromophore molecules have been used as chromogenic units, displaying various colors and/or uorescence. In addition, uoride-binding motifs such as urea, 17,18 thiourea, 19,20 hydrazide, 21,22 indole, 23,24 and imidazole 23,25 groups have been adopted for selective recognition of uoride. The receptor groups mostly recognize uoride by Hbonding or deprotonation of the -NH moiety.…”

Section: Introductionmentioning

confidence: 99%

A hydrazide organogelator for fluoride sensing with hyperchromicity and gel-to-sol transition

Park

Lee

et al. 2020

RSC Adv.

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Colorimetric anion sensor based on receptor having indole- and thiourea-binding sites

Abstract: A new colorimetric sensor having nitro-substituted indole and bisthiocarbonohydrazone units for selective fluoride and acetate ions has been designed and synthesized.

Cited by 20 publications

References 49 publications

Molecular Details of Acetate Binding to a New Diamine Receptor by NMR and FT-IR Analyses

Molecular Details of Acetate Binding to a New Diamine Receptor by NMR and FT-IR Analyses

Synthesis, fluorescence, and sorption properties of cobalt coordination polymers of the N,N′-bis(4-pyridylmethyl)naphthalene diimide ligand

A hydrazide organogelator for fluoride sensing with hyperchromicity and gel-to-sol transition

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