• Title/Summary/Keyword: Spirolactam

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Study of HOMO and LUMO Energy Levels for Spirolactam Ring Moiety Using Electrochemical Approach

  • Kim, Hyungjoo;Lee, Sehoon;Son, Young-A
    • Textile Coloration and Finishing
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    • v.25 no.2
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    • pp.83-88
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    • 2013
  • Rhodamine dyes have been studied in various scientific areas due to their excellent photophysical properties. In particular, these rhodamine dyes are one of the most famous fluorophores as signal unit in chemosensor study. This is related to spirolactam ring system in rhodamine dyes. When the spirolactam ring is closed, there is nonfluorescence and colorless. Whereas, ring-opening of the corresponding spirolactam induces strong fluorescence and color. These absorption and emission changes are related to structural changes as well as electron energy potential levels such as HOMO and LUMO values. In this study, two different structures of rhodamine 6G hydrazide depending on the spirolactam ring system were investigated using absorption measurement, electrochemical measurement and computational calculations.

Electrochemical Study on Rhodamine 6G-Indole Based Dye for HOMO and LUMO Energy Levels

  • Kim, Hyungjoo;Lee, Do-Hyun;Son, Young-A
    • Textile Coloration and Finishing
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    • v.25 no.1
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    • pp.7-12
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    • 2013
  • The energy levels are very important to investigate properties of organic dye materials. These values of energy levels can be calculated and compared with absorption spectra, cyclic voltammetric measurement and computer simulative calculation. In this study, absorption and emission changes were observed by complexation between rhodamine 6G based dye and mercury. This is related to spirolactam ring system of rhodamine 6G based dye. According to structural change of this dye, HOMO and LUMO energy levels were investigated and determined by their values with different approaches.

Characteristics of HOMO and LUMO Energy Potentials toward Rhodamine 6G-Naphthaldehyde Chemosensor

  • Kim, Hyungjoo;Lee, Do-Hyun;Son, Young-A
    • Textile Coloration and Finishing
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    • v.25 no.1
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    • pp.1-6
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    • 2013
  • Nowdays, the computational simulation of molecular energy potentials and the empirical evidence using electrochemical reduction/oxidation values are very significant factors to predict of molecule's energy potentials. The prepared chemosensor herein consists of spirolactam ring system in the structure, providing intra-structural change with metal cation binding. In this study, rhodamine 6G-Naphthaldehyde chemosensor was determined and compared with HOMO/LUMO energy levels by computational calculation and cyclic voltammogram method.

Synthesis and Fluorescent Properties of New Rhodamine B Containing Phenothiazine Moiety (새로운 로다민 B 페노시아진 유도체의 합성과 형광 특성)

  • Son, Moon Su;Chang, Seung Hyun
    • Journal of Environmental Science International
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    • v.24 no.7
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    • pp.955-960
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    • 2015
  • A colorimetric chemosensors $Sn^{2+}$ have been designed and synthesized by three steps. The spirolactam ring-opening process of rhodamine B is one of the most useful mechanisms for controlling fluorescence properties. Herein, new fluorescent chemosensors 1 and 2 based on rhodamine B containing phenothiazine derivertive were synthesized. They exhibit selective fluorescence enhancement behaviour in the presence of $Sn^{2+}$ ion. Complexation between these compounds and the metal cations were confirmed through continuous variation method. It is observed that compounds 1, 2, and $Sn^{2+}$ ion are complexed by 1:1 formation. Especially the proposed compounds 1 and 2 exhibit quick, simple and facile synthetic route.

Synthesis of Novel Fluorescent Dye Based on Fluorescein

  • Hwang, Ji-Yong;Son, Young-A
    • Textile Coloration and Finishing
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    • v.26 no.3
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    • pp.272-276
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    • 2014
  • The functional materials have been developed as a promising research topic toward the end uses for organic materials and applications. In this study, fluorescein based dye was synthesized by three step reaction. We have designed and synthesized the colorimetric dye through the reactions of fluorescein and methoxy group and ethylene diamine and squaric acid. The structure of the non-fluorescent spirolactam was elucidated by $^1H$-NMR, LC-Mass and FT-IR analyzes. Further studies are in progress to understand the effects of various substituent during the recognition process and to develop fluorescein based sensors for cations or anions.

Design and Synthesis of Novel Rhodamine-based Chemosensor Probe Toward Cu2+ Cation

  • Son, Young-A
    • Textile Coloration and Finishing
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    • v.26 no.1
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    • pp.7-12
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    • 2014
  • Nowdays, fluorescent rhodamine chemosensors have attracted a worldwide interest due to its ability to selectively detect heavy and transition metal cations. Due to the importance in environmental and biological toxic effects, the developments of fluorescent chemosensors have been received considerable attention in recent. Especially, a rhodamine-based chemosensor probes have been proved to be useful by exhibiting the efficient "off-on" fluorescence switching toward selected metal cations. This fluorophore can undergo the transformation from non-fluorescent and colorless spirolactam derivative to fluorescent ring-open form. In this study, a new fluorescent chemosensor was synthesized using rhodamine B through two-step procedures, and its selectivity and related optical property were characterized. Selectivity and sensitivity was found toward $Cu^{2+}$ guest molecules and then related optical properties of rhodamine B based fluorescent chemosensor compound were characterized using discussed. In addition, computational calculation was used to determine the HOMO/LUMO values.

Determination of Mercury Ion in Contaminated Soil by Rhodamine B Hydrazide (형광화학센서를 이용한 용출기반 토양 수은 오염조사)

  • Kim, Kyungtae;Park, Junboum
    • Journal of Soil and Groundwater Environment
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    • v.21 no.3
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    • pp.1-5
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    • 2016
  • Rhodamine B Hydrazide as a novel fluorescent and colorimetric probe exhibiting remarkably selective fluorescence enhancement toward Hg2+ ion over other 16 metal ions is herein introduced. The probe reacts with Hg2+ ion followed by its spirolactam ring-opening to give a remarkable enhancement of absorption maximum at 550 nm as well as an enhanced fluorescence intensity at 580 nm in aqueous media. Upon titration with Hg2+ ion in various concentration of 10~200 uM, we found that the probe shows a marked color change from colorless to pink, enabling naked-eye detection toward mercury ion. In addition, in the presence of Hg2+ ion, the probe gave rise to change from non-florescence to strong orange fluorescence (Off-On) with a good linearity of R2=0.97. This preliminary results demonstrate that the fluorescent chemosensor we herein introduced can open a new strategy for marked selective and sensitive detection of mercury ions in contaminated soil containing various metal ions.

Turn-On Type Fluorogenic and Chromogenic Probe for the Detection of Trace Amount of Nitrite Ion in Water

  • Saleem, Muhammad;Abdullah, Razack;Hong, In Seok;Lee, Ki-Hwan
    • Bulletin of the Korean Chemical Society
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    • v.34 no.2
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    • pp.389-393
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    • 2013
  • A rhodamine B-based fluorescent probe for nitrite ion ($NO{_2}^-$) has been designed, synthesized, characterized and its properties for recognition of $NO{_2}^-$ were studied. Nearly non fluorescent probe upon reaction with nitrite ion significantly triggered the fluorescence. Fluorescence response is based on ring opening of the spirolactam of rhodamine B phenyl hydrazide showing maximum absorbance at 552 nm and maximum emission at 584 nm. Probe 3 exhibited high sensitivity and extreme selectivity for nitrite ion over other common ions and oxidants ($Cl^-$, $ClO^-$, $ClO{_2}^-$, $ClO{_3}^-$, $ClO{_4}^-$, $SO{_4}^{2-}$, $SiO{_3}^{2-}$, $NO{_3}^{2-}$, $CO{_3}^{2-}$) examined in methanol water (1:1, v/v) at pH 7.0. The probe might be a new efficient tool for detection of nitrite ion in natural water and biological system.