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Jeong, Jong woo,Angupillai, Satheshkumar,Kim, Ick Jin,Jeong, Jaemyeng,Kim, Hak-Soo,So, Hee-Soo,Son, Young-A Elsevier 2016 Sensors and actuators. B Chemical Vol.237 No.-
<P><B>Abstract</B></P> <P>Two new naphthalimide-based chemodosimeters, <B>R1</B> and <B>R2</B>, for CN<SUP>−</SUP> anions were designed and synthesized. For the sensing event, the dicyanovinyl group and ethyl cyanoacrylate groups acted as the recognition sites in conjunction with the electron-withdrawing naphthalimide fluorophore group. Both receptors exhibited high sensitivity and selectivity, with apparent response signals that could be observed by the naked eye, even in the presence of various other interference anions. We used electronic and fluorescent spectroscopic techniques, NMR titration measurements and HRMS techniques to rationalize the sensing mechanisms of these two receptors. Upon the addition of CN<SUP>−</SUP>, the fluorescence of <B>R1</B> and <B>R2</B> was distinctly enhanced. Specifically, compared with <B>R2</B>, <B>R1</B> exhibited a higher affinity and a higher sensitivity (detection limit of 9.69nM) toward CN<SUP>−</SUP> in THF- H<SUB>2</SUB>O (3:7, v/v) mixture.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Michael addition based chemodosimeters were synthesized to sense CN<SUP>−</SUP>. </LI> <LI> The sensing of CN<SUP>−</SUP> ion has been attributed due to the restriction of PET transition. </LI> <LI> These chemodosimeters <B>R1</B> &<B>R2</B> have been sense CN<SUP>−</SUP> up to trace level (10<SUP>−9</SUP> M). </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
So, H.S.,Angupillai, S.,Son, Y.A. Elsevier Sequoia 2016 Sensors and actuators. B Chemical Vol.235 No.-
A new rhodamine-based probe (RTU) was prepared as a colorimetric/fluorescent probe for the selective detection of DCP (a mimic of the Soman nerve agent) with a broad pH range of 7-11.0. RTU contains two reactive sites: (i) a nucleophilic thiourea group able to undergo complexation with electrophilic phosphorous and (ii) a spirolactam carbonyl group that acts as a reactive site for phosphorous. RTU exhibits great photostability, high sensitivity, and good selectivity for DCP (in both the liquid and vapor phases) compared with other reactive species, such as metal ions and H<SUP>+</SUP>, under alkaline conditions. Upon mixing with DCP in 3% Et<SUB>3</SUB>N-DMF, the spirolactam of RTU opened, which triggered the dramatic enhancement of both fluorescence and absorbance intensity and a color change of the solution. The probe displays a linear response to DCP in the range from 2.0x10<SUP>-5</SUP> to 15x10<SUP>-5</SUP>M with a detection limit of 1.42x10<SUP>-7</SUP>M. The kinetics results indicate that RTU exhibits instantaneous sensing behavior within a few minutes. Its recognition behavior toward DCP was investigated by <SUP>1</SUP>H NMR, FAB-MS, and <SUP>31</SUP>P NMR. Portable kits were developed and tested to demonstrate the practical application of RTU in real-time monitoring.
Kim, Hak-Soo,Angupillai, Satheshkumar,Son, Young-A Elsevier 2016 Sensors and actuators. B, Chemical Vol.222 No.-
<P><B>Abstract</B></P> <P>A simple 4-nitrosalicylaldimine-based receptor equipped with rhodamine B moiety (RB-HN) has been designed and synthesized as an “OFF–ON–OFF” dual sensor for the detection of Cu<SUP>2+</SUP> and Al<SUP>3+</SUP> ions, which exhibits high sensitivity over other metal ions. The chemosensor RB-HN demonstrates selective optical recognition for Cu<SUP>2+</SUP> and fluorescence recognition for Al<SUP>3+</SUP> over commonly coexistent metal ions in DMSO–H<SUB>2</SUB>O media. The LODs of the RB-HN for Cu<SUP>2+</SUP> and Al<SUP>3+</SUP> were 4.726×10<SUP>−7</SUP> and 4.43×10<SUP>−7</SUP> M, respectively. A coordination mode with 1:1 stoichiometry was proposed between RB-HN and Cu<SUP>2+</SUP>/Al<SUP>3+</SUP> by the <SUP>1</SUP>H NMR binding studies. The RB-HN complex with Cu<SUP>2+</SUP> and Al<SUP>3+</SUP> ions exhibits “turn on–off” behavior and is highly reversible with EDTA. In addition, the UV–vis and fluorescence changes of RB-HN by the inputs of Cu<SUP>2+</SUP> and Al<SUP>3+</SUP> have been used to construct a combinational logic circuit at the molecular level. Moreover, a novel selective and sensitive solid sensor (PEGDMA-RB-HN) was designed to detect and extract Al<SUP>3+</SUP> ions from aqueous solution. Furthermore, the sensitivity of the solid sensor was demonstrated by confocal laser scanning microscopy (CLSM) and scanning electron microscopy (SEM). The extracting capacity of the solid sensor was validated with ICP-AES, and it was significantly lower than the WHO recommendations for drinking water.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Dual response receptor RB-HN material has been synthesized to detect Cu<SUP>2+</SUP> and Al<SUP>3+</SUP> ion in DMSO/water medium. </LI> <LI> RB-HN shows high reversibility with EDTA and reflect “OFF–ON–OFF” recognizing property. </LI> <LI> Molecular logic gate has been developed as INHIBIT logic gate with a YES logic function. </LI> <LI> At first PEGDMA encapsulated RB-HN has been used to detect and extract the Al<SUP>3+</SUP> ion from aqueous medium. </LI> </UL> </P>
Kim, Myeong Jin,Angupillai, Satheshkumar,Min, Kyeongsu,Ramalingam, Manivannan,Son, Young-A. American Chemical Society 2018 ACS APPLIED MATERIALS & INTERFACES Vol.10 No.29
<P>The topochemical polymerization of diacetylenes (DAs) is closely related to the length of their alkyl chain. DA monomers have two types of alkyl chain side groups: the inner alkyl chain and the outer alkyl chain, that is, the peripheral alkyl chain. Herein, we designed and synthesized a series of DA monomers that possess bis-amide linkages with different peripheral alkyl chains (<I>n</I> = 6-9; <B>DA1-DA4</B>). The peripheral alkyl chain length of these DA monomers exhibits an odd/even effect on topochemical polymerization. The polymerization of DAs was achieved only when <I>n</I> is an odd number, whereas no polymerization occurred when n is an even number. The odd/even effect on the topochemical polymerization was also investigated using ab initio density functional theory calculations. The thermochromic reversibility of polydiacetylenes (PDAs) was investigated using UV-vis absorption spectroscopy at temperatures ranging from 20 to 60 °C. Monomer <B>DA2</B> was used as a single-component ink solution in a fountain pen that can be transformed into thermochromic letters on conventional paper. Furthermore, a PDA-embedded polyethylene oxide film was included to monitor the thermochromic reversibility and was found to exhibit excellent thermochromic reversibility between 20 and 100 °C and stability, enabling storage for a few months without deformation. Finally, a green-colored patterned polymer film is readily obtained by a subtractive color (blue and yellow) mixing method and exhibits high thermochromic reversibility at temperatures between 20 and 100 °C.</P> [FIG OMISSION]</BR>
Kim, H.S.,Angupillai, S.,Jeong, Y.M.,Park, J.S.,Kim, C.H.,Son, Y.A. Elsevier Sequoia 2017 Sensors and actuators. B Chemical Vol.240 No.-
Two novel through-bond energy transfer (TBET) based naphthoquinone derivatives, R1 and R2, have been designed and synthesized with characteristics of a dyad (rhodamine-quinone) and a triad (rhodamine-quinone-rhodamine), respectively. Probes R1 and R2 selectively sense Hg<SUP>2+</SUP> ions over other common interference metal ions in aqueous-methanol medium with a broad pH range (6.0-8.0). By the combination of dual functions, (i.e., fluorescence off-on (rhodamine) and TBET off-on (through a conjugation linker) processes), the proposed TBET-probes exhibit very large pseudo-Stokes shifts, with a wavelength difference ~210nm, and high energy transfer efficiency for the detection of Hg<SUP>2+</SUP> with a detection limit of 41nM. The fluorescence intensity of the triad (R2) is nearly 2 orders of magnitude greater than that of the dyad R1 due to the existence of two rhodamine fragments. The OFF-ON fluorescence effect of the TBET cassettes regains the ON-OFF mode by subsequent addition of the I<SUP>-</SUP> ion. The optical restoring behavior of the R1/R2-Hg<SUP>2+</SUP> complex with I<SUP>-</SUP> could be potentially be applied as an INHIBIT molecular logic gate with the combination of YES and NOT functions. Finally, the Hg<SUP>2+</SUP> ion sensing ability of TBET probes R1 and R2 was utilized in a HeLa cell imaging application, and the probe R1 was used to monitor the Hg<SUP>2+</SUP> ion in live zebrafish.
Yu, H.,Lee, J.Y.,Angupillai, S.,Wang, S.,Feng, S.,Matsumoto, S.,Son, Y.A. Pergamon 2015 Spectrochimica acta. Part A, Molecular and biomole Vol.151 No.-
<P>Turn 'off-on' chemosensor 2-(-2-((3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)imino)ethylidene)-N-phenylhydrazine-1-carbothioamide (RBS) was designed and synthesized. Using the naked eye, RBS showed favorable observation characteristics with both Cu2+ and F- ions. The various modes of sensitivity shown by RBS toward the Cu2+ and F- ions were investigated by spectral techniques, including UV-Vis, fluorescence and H-1 NMR spectroscopy. The Job's plot indicated the formation of 1:1 complex between RBS and Cu2+/F-. The binding constant of the RBS-guest(-) complexes were found to be 1.3 x 10(4) and 6.2 x 10(3) M-1 for the RBS-Cu2+ and RBS-F-, respectively. (C) 2015 Elsevier B.V. All rights reserved.</P>
Ku, Kyo-Sun,Muthukumar, Palanisamy,Angupillai, Satheshkumar,Son, Young-A Elsevier 2016 Sensors and actuators. B Chemical Vol.236 No.-
<P><B>Abstract</B></P> <P>In this paper, a novel fluorescent probe based on a rhodamine 6G derivative (RG-HN) was designed and synthesized for the recognition of Al<SUP>3+</SUP>. The synthesized RG-HN showed high selectivity towards Al<SUP>3+</SUP> in CH<SUB>3</SUB>CN in the presence of other competitive metal ions. The addition of Al<SUP>3+</SUP>into RG-HN led to a visible color change and an off-on fluorescence change due to the opening of the spirolactam ring. The detection limit was calculated based on 3δ/k and found to be 2.6×10<SUP>−8</SUP> M. The Job’s plot and LCMS spectrum clearly suggested the formation of a 2:1 complex of RG-HN with Al<SUP>3+</SUP>. Further, RG-HN thin films were prepared and used as probes for the detection of Al<SUP>3+</SUP> in completely aqueous media. RG-HN thin film showed a visible color change after immersing in Al<SUP>3+</SUP> in water. Changes in the morphology of the RG-HN thin film upon sensing of Al<SUP>3+</SUP> were studied by scanning electron microscopy.</P> <P><B>Highlights</B></P> <P> <UL> <LI> A new rhodamine 6G based chemosensor (RG-HN) was synthesized and its chemical structure was confirmed by <SUP>1</SUP>HNMR, <SUP>13</SUP>CNMR and ESI-mass. </LI> <LI> RG-HN showed good selectivity towards Al<SUP>3+</SUP>. </LI> <LI> RG-HN thin film was prepared by dip-coating method. </LI> <LI> RG-HN thin film recognizes Al<SUP>3+</SUP> in 100% of aqueous media. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Kim, C.,Hwang, J.Y.,Ku, K.S.,Angupillai, S.,Son, Y.A. Elsevier Sequoia 2016 Sensors and actuators. B, Chemical Vol.228 No.-
A conventional colorimetric/fluorescent chemosensor R2PP was used to detect the Al<SUP>3+</SUP> ion in CH<SUB>3</SUB>CN/DMSO (2:8, v/v) medium at nanomolar level (LOD=8.5x10<SUP>-9</SUP>M). The 2:1 binding stoichiometry of the metal complex was established on the basis of combined UV-vis and fluorescence spectroscopy and ESI-MS. The binding sites were confirmed by FT-IR and <SUP>1</SUP>H NMR spectroscopy and ESI mass analysis. This conventional chemosensor R2PP was renovated from non-aqueous medium to aqueous medium by R2PP blended polyurethane electrospun (ES) nanofibers. This ES nanofibers has selectively sense the Al<SUP>3+</SUP> over other transition metal cations in solid state. The ES nanofibers could detect Al<SUP>3+</SUP> onsite and in real time, and the color of the nanofibers changed rapidly after they were immersed in an aqueous solution (video S1). In addition, the R2PP blended nanofibers exhibits reversibility and 'OFF-ON-OFF' sensing behavior with Na<SUB>2</SUB>EDTA. Finally, the R2PP-nanofiber kit has been successfully utilized to detect Al<SUP>3+</SUP> in real sample testing.