• Title/Summary/Keyword: Merocyanine

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Photochromic Behavior and Its Stability of a New Bifunctional Dye Composed of Spirobenzopyran and a Cinnamoyl Moiety

  • Shen Kaihua;Kim Jae Hong;Kim Go Woon;Cho Min Ju;Lee Sang Kyu;Choi Dong Hoon
    • Macromolecular Research
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    • v.13 no.3
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    • pp.180-186
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    • 2005
  • A novel bifunctional dye composed of spirobenzopyran and a cinnamoyl moiety was prepared and its photochromic behavior under the illumination of monochromatic UV light was investigated. This colorless bifunctional dye exhibits typical photochromism in both the film and in solution, through the structural and geometrical transformation from spirobenzopyran to merocyanine accompanied by a photocrosslinking reaction between the cinnamoyl moieties. Two kinds of photochemical reaction were selectively achieved by irradiation with monochromatic UV light at wavelengths of 275 and 365 nm, respectively. The effect of the selective photochemical reaction on the photochromism of the dye and its decaying behavior was investigated.

Fabrication of Spiropyran-functionalized Photochromic Hydrogel Lenses

  • Lee, Cheol Woo;Badon, Isabel Wen;Kim, Boram;Ryu, Geun-Chang;Kim, Ho-Joong
    • Journal of Integrative Natural Science
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    • v.11 no.1
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    • pp.39-43
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    • 2018
  • Poly(hydroxyethyl methacrylate)-based hydrogels were surface-functionalized with spiropyran (SP) derivatives to obtain photochromic contact lenses. The contact lens reversibly changes from colorless to purple as response to UV light since colorless ring-closed SP state converts to purple ring-opened merocyanine (MC) state under UV light irradiation. The purple contact lens emits red light at 640 nm. Importantly, the presence of SP segments did not significantly affect the equilibrium water content (EWC) of the lens. SP-functionalized hydrogel lenses may find potential applications in developing light-adaptive ophthalmic materials.

Surface Modification Using Spiropyran-Derivative and Its Analysis of Surface Potential Induced by UV (스파이로파이란에 의한 표면 개질 및 자외선에 의해 유도된 표면 전위에 대한 분석)

  • Lee, Bong-Soo;Han, Dong-Keun;Son, Tae-Il;Jung, Young-Hwan
    • Journal of the Korean Chemical Society
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    • v.55 no.3
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    • pp.478-485
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    • 2011
  • Merocyanine derivatives transformed from spiropyran-containing compounds by irradiating the light of ultraviolet (UV) include zwitterion of phenolate anion and amine cation. Complexation of this phenolate anion on merocyaninemodified surface and Ni ion among metal ions led to a change of surface charge and it was measured with kelvin prove force microscopy (KFM). We found that the resultant surface potential decreased linearly as UV-exposed time increased, and finally were saturated. Also it was analyzed through XPS the immobilized amount of Ni ions was increased according to increase of UV-exposed time. It is considered that these properties could be applied for detection and a quantitative control of different metal ions. Further research is to aim construct specific scaffold/matrix which enable high selective, high sensitive and, especially, a quantitative immobilization of metal ions-binding biomaterials such as proteins and cells.

Observation of Electrical and Optical Images of Organic Thin Films Using SPM (SPM을 이용한 유기박막의 전기.광학 이미지 관찰)

  • Yoo, Seung-Yeop;Lee, Seung-Jun;Jin, Chel-Nam;Shin, Hoon-Kyu;Kwon, Young-Soo
    • Proceedings of the KIEE Conference
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    • 1999.07d
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    • pp.1777-1779
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    • 1999
  • SMM is a dynamic noncontact electric force microscopy that allows simultaneous access to the electrical properties of molecular system such as surface potential, surface charge, dielectric constant and conductivity along with the topography. SNOAM is a new tool for surface imaging which was introduced as one application of AFM. Operated with non-contact forces between the optical fiber and sample as well as equipped with the piezoscanners, the instrument reports on surface topology without damaging or modifying the surface for measuring of optical characteristic in the films. Here we report our recent results of its application to nanoscopic study of domain structures and electrical functionality in organic thin films by SMM. Furthermore, we have illustrated the SNOAM image in obtaining the merocyanine dye films as well as the optical image.

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Analysis of Surface Morphology and Optical Transmission Features in LB Films by SNOAM (SNOAM에 의한 LB막의 표면모폴로지 및 광투과상 해석)

  • Lee, Seung-Jun;Jung, Sang-Burm;Yoo, Seung-Yeop;Sin, Hun-Gyu;Park, Jae-Chul;Kwon, Young-Soo
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • 2000.04b
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    • pp.108-111
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    • 2000
  • We will illustrate the topographical structure and optical structure of the merocyanine dye LB films obtained by the scanning near-field optical/atomic force microscopy (SNOAM). SNOAM was recognized as a powerful tool to modify the surface as well as to characterize the topography of the surface at atomic resolution, especially for optical reaction materials. SNOAM images showed that the topographical and optical structures of these films were not only depended on the chemical property but also physical property. In the continuous measurement on these dyes, the appearance of near-field optical transmission images showed a certain dependence on the kinds of dyes and the mutual mixing ratios of dyes. These experimental results suggest that there is a certain kind of interaction between these two dyes.

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Observation of Morphology, Surface potential and Optical Transmission Images in the Thin Film Using SPM (SPM을 이용한 박막의 모폴로지, 표면전위와 광투과이미지 관찰)

  • Shin, Hoon-Kyu;Kwon, Young-Soo
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • 2000.05b
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    • pp.327-330
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    • 2000
  • The scanning Maxwell-stress microscopy (SMM) is a dynamic noncontact electric force microscopy that allows simultaneous access to the electrical properties of molecular system such as surface potential, surface charge, dielectric constant and conductivity along with the topography. The Scanning near-field optical / atomic force microscopy (SNOAM) is a new tool for surface imaging which was introduced as one application of the atomic force microscope (AFM). Operated with non-contact forces between the optical fiber and sample as well as equipped with the piezoscanners, the instrument reports on surface topology without damaging or modifying the surface for measuring of optical characteristic in the films. We report our recent results of its application to nanoscopic study of domain structures and electrical functionality in organic thin films by SMM. Furthermore, we have illustrated the SNOAM image in obtaining the merocyanine dye films as well as the optical image.

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Preparation of Polymeric Self-Assembly and Its Application to Biomaterials

  • Cho, Chong-Su;Park, In-Kyu;Nah, Jae-Woon;Toshihiro Akaike
    • Macromolecular Research
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    • v.11 no.1
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    • pp.2-8
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    • 2003
  • The self-assembly of polymers can lead to supramolecular systems and is related to the their functions of material and life sciences. In this article, self-assembly of Langmuir-Blodgett (LB) films, polymer micelles, and polymeric nanoparticles, and their biomedical applications are described. LB surfaces with a well-ordered and layered structure adhered more cells including platelet, hepatocyte, and fibroblast than the cast surfaces with microphase-separated domains. Extensive morphologic changes were observed in LB surface-adhered cells compared to the cast films. Amphiphilic block copolymers, consisting of poly(${\gamma}$-benzyl L-glutamate) (PBLG) as the hydrophobic part and poly(ethylene oxide) (PEO) [or poly(N-isopropylacrylamide) (PNIPAAm)] as the hydrophilic one, can self-assemble in water to form nanoparticles presumed to be composed of the hydrophilic shell and hydrophobic core. The release characteristics of hydrophobic drugs from these polymeric nanoparticles were dependent on the drug loading contents and chain length of the hydrophobic part of the copolymers. Achiral hydrophobic merocyanine dyes (MDs) were self-assembled in copolymeric nanoparticles, which provided a chiral microenvironment as red-shifted aggregates, and the circular dichroism (CD) of MD was induced in the self-assembled copolymeric nanoparticles.

Synthesis and Photovoltaic Properties of Dendritic Photosensitizers containing Carbazole and Phenothiazine for Dye-sensitized Solar Cells (카바졸과 페노시아진을 이용한 염료감응형 태양전지의 염료 합성과 광적특성)

  • Kim, MyeongSeok;Jung, DaeYoung;Kim, JaeHong
    • 한국신재생에너지학회:학술대회논문집
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    • 2010.06a
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    • pp.89.1-89.1
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    • 2010
  • Since Gratzel and co-workers developed a new type of solar cell based on the nanocrystalline $TiO_2$ electrode, dye-sensitized solar cells (DSSCs) have attracted considerable attention on account of their high solar energy-to-conversion efficiencies (11%), their easy manufacturing process with low cost production compared to conventional p-n junction solar cells. The mechanism of DSSC is based on the injection of electrons from the photoexcited dye into the conduction band of nanocrystalline $TiO_2$. The oxidized dye is reduced by the hole injection process from either the hole counter or electrolyte. Thus, the electronic structures, such as HOMO, LUMO, and HOMO-LUMO gap, of dye molecule in DSSC are deeply related to the electron transfer by photoexcitation and redox potential. To date, high performance and good stability of DSSC based on Ru-dyes as a photosensitizer had been widely addressed in the literatures. DSSC with Ru-bipyridyl complexes (N3 and N719), and the black ruthenium dye have achieved power conversion efficiencies up to 11.2% and 10.4%, respectively. However, the Ru-dyes are facing the problem of manufacturing costs and environmental issues. In order to obtain even cheaper photosensitizers for DSSC, metal-free organic photosensitizers are strongly desired. Metal-free organic dyes offer superior molar extinction coefficients, low cost, and a diversity of molecular structures, compared to conventional Ru-dyes. Recently, novel photosensitizers such as coumarin, merocyanine, cyanine, indoline, hemicyanine, triphenylamine, dialkylaniline, bis(dimethylfluorenyl)-aminophenyl, phenothiazine, tetrahydroquinoline, and carbazole based dyes have achieved solar-to-electrical power conversion efficiencies up to 5-9%. On the other hand, organic dye molecules have large ${\pi}$-conjugated planner structures which would bring out strong molecular stacking in their solid-state and poor solubility in their media. It was well known that the molecular stacking of organic dyes could reduce the electron transfer pathway in opto-electronic devices, significantly. In this paper, we have studied on synthesis and characterization of dendritic organic dyes with different number of electron acceptor/anchoring moieties in the end of dendrimer. The photovoltaic performances and the incident photon-to-current (IPCE) of these dyes were measured to evaluate the effects of the dendritic strucuture on the open-circuit voltage and the short-circuit current.

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Photovoltaic Properties of Dendritic Photosensitizers containing multi-chromophore for Dye-sensitized Solar Cells (multi-chromophore를 가지는 유기염료의 DSSC 광전변환거동)

  • Kim, MyeongSeok;Cheon, Jong Hun;Jung, DaeYoung;Kim, JaeHong
    • 한국신재생에너지학회:학술대회논문집
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    • 2011.05a
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    • pp.117.2-117.2
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    • 2011
  • Since Gratzel and co-workers developed a new type of solar cell based on the nanocrystalline TiO2 electrode, dye-sensitized solar cells (DSSCs) have attracted considerable attention on account of their high solar energy-to-conversion efficiencies (11%), their easy manufacturing process with low cost production compared to conventional p-n junction solar cells. The mechanism of DSSC is based on the injection of electrons from the photoexcited dye into the conduction band of nanocrystalline TiO2. The oxidized dye is reduced by the hole injection process from either the hole counter or electrolyte. Thus, the electronic structures, such as HOMO, LUMO, and HOMO-LUMO gap, of dye molecule in DSSC are deeply related to the electron transfer by photoexcitation and redox potential. To date, high performance and good stability of DSSC based on Ru-dyes as a photosensitizer had been widely addressed in the literatures. DSSC with Ru-bipyridyl complexes (N3 and N719), and the black ruthenium dye have achieved power conversion efficiencies up to 11.2% and 10.4%, respectively. However, the Ru-dyes are facing the problem of manufacturing costs and environmental issues. In order to obtain even cheaper photosensitizers for DSSC, metal-free organic photosensitizers are strongly desired. Metal-free organic dyes offer superior molar extinction coefficients, low cost, and a diversity of molecular structures, compared to conventional Ru-dyes. Recently, novel photosensitizers such as coumarin, merocyanine, cyanine, indoline, hemicyanine, triphenylamine, dialkylaniline, bis(dimethylfluorenyl)-aminophenyl, phenothiazine, tetrahydroquinoline, and carbazole based dyes have achieved solar-to-electrical power conversion efficiencies up to 5-9%. On the other hand, organic dye molecules have large ${\pi}$-conjugated planner structures which would bring out strong molecular stacking in their solid-state and poor solubility in their media. It was well known that the molecular stacking of organic dyes could reduce the electron transfer pathway in opto-electronic devices, significantly. In this paper, we have studied on synthesis and characterization of dendritic organic dyes with different number of electron acceptor/anchoring moieties in the end of dendrimer. The photovoltaic performances and the incident photon-to-current (IPCE) of these dyes were measured to evaluate the effects of the dendritic strucuture on the open-circuit voltage and the short-circuit current.

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