• Transactions on Electrical and Electronic Materials
• /
• v.16 no.3
• /
• pp.162-167
• /
• 2015

To investigate the effect of fluoro groups substitution on poly(p-phenylenevinylene) derivatives, poly(2,3,5,6- tetrafluoro-p-phenylenevinylene-alt-N-ethylhexyl-3,6-carbazolevinylene), PCTF-PPV, and poly[2,3,5,6-tetrafluoro-p-phenylenevinylene-alt-2-methoxy-5-(2-ethylhexyloxy)-p-phenylenevinylene], PMTF-PPV, were synthesized by the well-known Wittig condensation polymerization process. To compare the influences of fluoro groups, no fluoro groups containing model polymers, poly(p-phenylenevinylene-alt-N-ethylhexyl-3,6-carbazolevinylene), PCPPPV and poly[p-phenylenevinylene-alt-2-methoxy-5-(2-ethylhexyloxy)-p-phenylenevinylene], p-PMEH-PPV, were also synthesized. The resulting polymers were completely soluble in common organic solvents and exhibited good thermal stability up to 300℃. The polymers showed UV-visible absorbance and photoluminescence (PL) in the ranges of 259~452 nm and 500~580 nm, respectively. The tetrafluorophenyl containing PCTF-PPV and PMTF-PPV showed relatively red-shifted PL peaks at 521 nm and 580 nm, respectively, compared to that of non-fluoro groups containing polymers (PCP-PPV: 500 nm and p-PMEH-PPV: 539 nm). The single-layer light-emitting diode was fabricated in a configuration of ITO/polymer/Al. Electroluminescene (EL) emissions of PCP-PPV, PCTF-PPV, p-PMEH-PPV and PMTF-PPV were shown at 507, 524, 556, and 616 nm, respectively.

• Bulletin of the Korean Chemical Society
• /
• v.34 no.4
• /
• pp.1108-1114
• /
• 2013

Photochemical reactions of fluoro- vs. nonfluoro-substituted polymethylenoxy chain linked phthalimide were carried out to explore how electronegative fluorine atoms inside the donor chain influence photocyclization reaction efficiencies and to briefly determine the alkali metal binding properties of the photoproducts. The results of this study show that the fluorine-substituted donor chain linked phthalimide undergoes inefficient photocyclization via single electron transfer (SET)-induced excited state pathways to generate 14-membered cyclic amidol compared to nonfluoro-analog due to low electron donor ability of the terminal oxygen donor site. These results show that photoinduced intramolecular SET processes arising from ${\alpha}$-silyl ether electron donors to phthalimides are largely dependent on the kinds of substituents inside donor chain. Finally, a preliminary study with the cyclic amidols generated in this effort showed that they have weak alkali metal cation binding properties regardless of absence/presence of fluoro-substituents.

• Nuclear Engineering and Technology
• /
• v.4 no.4
• /
• pp.294-300
• /
• 1972

CNDO/2 and INDO calculations have been carried out on varying geometries of methyl chloro-and fluoro-formates. Results show that the configuration in which halogen atom is trans to methyl group is the most stable. Atomic charges and overlap population show that the trans form is stabilized by conjugation of carbonyl double bend with the unshared pairs of the ether oxygen and by electrostatic attraction of carbonyl oxygen to methyl group. Dipole moments of the trans forms agree reasonably well with the experimental values but showed that any generalizations made with dipole moments from bond moments should be accepted with considerable reservations.

• Archives of Pharmacal Research
• /
• v.10 no.4
• /
• pp.239-244
• /
• 1987

An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methylithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparting geranyl fluoride, neryl fluoride, cinnamyl fluoride, E, E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(ptolyl)-2-heptene.

• Journal of the Korean Chemical Society
• /
• v.37 no.2
• /
• pp.249-254
• /
• 1993

N-p-nitrophenyl poly(m-phenylene isophthalamide) was obtained from treatment of poly(m-phenylene isophthalamide) with sodium hydride in dimethyl sulfoxide followed by the addition of 1-fluoro-4-nitrobenzene in 43 wt% yield. Its inherent viscosity was 0.606 g/cm${\cdot}$sec determined from a solution of 0.125 g of the above polymer dissolved in 25 ml of 98% sulfuric acid at $30^{\circ}C.$ In order to synthesize poly(m-phenylene isophthalamide), 1,3-phenylenediamine is allowed to react with isophthaloyl chloride in chloroform in the presence of triethylamine and added triethylamine hydrochloride. The value of inherent viscosity is 0.560 g/cm${\cdot}$sec measured at the same condition. The substitution ratio of N-p-nitrophenyl poly(m-phenylene isophthalamide) was to be 16.7∼47.0% by using the $^1H-NMR$ integration. When the higher inherent viscosity of poly(m-phenylene isophthalamide) was used, lower substitution ratio would be calculated.

• Polymer(Korea)
• /
• v.25 no.6
• /
• pp.796-802
• /
• 2001

Novel monomer for polybenzimidazole was prepared and polymerized via aromatic nucleophilic substitution reaction. Thus, N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was synthesized from the reaction of 4-methoxy-N-naphthyl-1,2-phenylenediamine and 4-fluorobenzoyl chloride. N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was converted to 2-(4-fluorobenzoyl)-5-hydroxy-1-naphthylbenzimidazole by ring closure and demethylation reaction. Polymerization was done in N-cyclohexyl-2-pyrrolidinone (CHP) containing potassium car bonate. The resulting polymer was soluble in N-methyl-2-pyrrolidinone (NMP) and had inherent viscosity of 0.38 dL/g (NMP at $30^{\circ}C$). The glass transition temperature ($T_g$ ) of the polybenzimidazole was $270^{\circ}C$. The thermogravimetric analysis (TGA) thermograms of this polymer showed 5% weight losses at $550^{\circ}C$ in nitrogen and at $540^{\circ}C$ in air.

• The Korean Journal of Nuclear Medicine
• /
• v.33 no.6
• /
• pp.527-536
• /
• 1999

Purpose: Radiotracers that bind to the central benzodiazepine receptor are useful for the investigation of various neurological and psychiatric diseases. [C-11]Flumazenil, a benzodiazepine antagonist, is the most widely used radioligand for central benzodiazepine receptor imaging by PET. We synthesized 3-(2-[F-18]fluoro)flumazenil, a new fluorine-18 ($t_{1/2}$= 110 min) labeled analogue of benzodiazepine receptor imaging agent, and evaluated in vivo for biodistribution in mice. Materials and Methods: Flumazenil (Ro 15-1788) was synthesized by a modification of the reported method. Precursor of 3-(2-[F-18]fluoro)flumazenil, the tosylated flumazenil derivative was prepared by the tosylation of the ethyl ester by ditosylethane. [F-18] labeling of tosyl substitued flumazenil precursor was performed by adding F-18 ion at $85^{\circ}C$ in the hot ceil for 20 min. The reaction mixture was trapped by C18 cartridge, washed with 10% ethanol, and eluted by 40% ethanol. Bidistribution in mice was determined after intravenous injection. Results: The total chemical yield of tosylated flumazenil derivative was ${\sim}40%$. The efficiency of labeling 3-(2-[F-18]fluoro)flumazenil was 66% with a total synthesis time of 50 min. Brain uptakes of 3-(2-[F-18]fluoro)flumazenil at 10, 30, 60 min after injection, were $2.5{\pm}0.37,\;2.2{\pm}0.26,\;2.1{\pm}0.11$ and blood activities were $3.7{\pm}0.43,\;3.3{\pm}0.07,\;3.3{\pm}0.09%ID/g$, respectively. Conclusion: We synthesized a tosylated flumazenil derivative which was successfully labeled with no-carrier-added F-18 by nucleophilic substitution.

• Journal of the Korean Ceramic Society
• /
• v.26 no.5
• /
• pp.601-608
• /
• 1989

Electrical properties of ZrF4-based heavy metla fluoride glasses were measured by the ac complex impedance method. The effects of alkali and chloride ions addition into fluoro zirconate glasses on the electrical conductivity were examined. The electrical conductivities of fluoride glasses show Arrhenian behavior in the temperature range of the experiment and were decreased by the addition of sodium fluoride up to 15mol%. Mixed alkali substitution resulted in conductivity minimum at intermediate composition which is commonly observed as mixed alkali effect' in alkali oxide glasses. Chloride ion substituted for fluoride ion was found to lower the conductivity.

• 한국신재생에너지학회:학술대회논문집
• /
• 2010.11a
• /
• pp.90.1-90.1
• /
• 2010

The design and fabrication of a metallic bipolar plate-gasket assembly for polymer electrolyte fuel cells (PEMFCs) is defined. This bipolar plate-gasket assembly was prepared by inserting a previously prepared bipolar plate in the specially designed gasket mold. For this aim, a proprietary fluoro-silicone based rubber was injected directly into the bipolar plate borders. Gaskets obtained like this showed the chemically / physically stable and the good sealibilty in typically operating PEM fuel cell conditions. And also, this bipolar plate-gasket assembly shows lots of advantages with respect to traditional PEMFCs stack assembling systems: useful application to automative stacking due to easy handling, reduced fabrication time, possibility of quality control and failed elements substitution. This bipolar plate-gasket assembly was evaluated in the short fuel cell stack and met the leakage requirement for normal operation both in short-term and in long-term operation. Especially, it was confirmed that this gasket could be applied successfully even in the high pressure FEM fuel cell systems(over 2.0 bar in absolute pressure).

• Nuclear Medicine and Molecular Imaging
• /
• v.40 no.4
• /
• pp.218-227
• /
• 2006

Purpose: The HSV1-tk reporter gene system is the most widely used system because of its advantage that direct monitoring is possible without the introduction of a separate reporter gene in case of HSV1-tk suicide gene therapy. In this study, we investigate the usefulness of the reporter probe (substrate), $9-(4-[^{18}F]Fluoro-3-hydroxymethylbutyl)$guanine ($[^{18}F]FHBG$) for non-invasive reporter gene imaging using PET in HSV1-tk expressing hepatoma model. Materials and Methods: Radiolabeled FHBG was prepared in 8 steps from a commercially available triester. The labeling reaction was carried out by NCA nucleophilic substitution with $K[^{18}F]/K2.2.2.$ in acetonitrile using N2-monomethoxytrityl-9-14-(tosyl)-3-monomethoxytritylmethylbutyl]guanine as a precursor, followed by deprotection with 1 N HCl. Preliminary biological properties of the probe were evaluated with MCA cells and MCA-tk cells transduced with HSV1-tk reporter gene. In vitro uptake and release-out studies of $[^{18}F]FHBG$ were performed, and was analyzed correlation between $[^{18}F]FHBG$ uptake ratio according to increasing numeric count of MCA-tk cells and degree of gene expression. MicroPET scan image was obtained with MCA and MCA-tk tumor bearing Balb/c-nude mouse model. Results: $[^{18}F]FHBG$ was purified by reverse phase semi-HPLC system and collected at around 16-18 min. Radiothemical yield was about 20-25%) (corrected for decay), radiochemical purity was >95% and specific activity was around >55.5 $GBq/{\mu}\;mol$. Specific accumulation of $[^{18}F]FHBG$ was observed in HSV1-tk gene transduced MCA-tk cells but not in MCA cells, and consecutive 1 hour release-out results showed more than 86% of uptaked $[^{18}F]FHBG$ was retained inside of cells. The uptake of $[^{18}F]FHBG$ was showed a highly significant linear correlation ($R^2=0.995$) with increasing percentage of MCA-tk numeric cell count. In microPET scan images, remarkable difference of accumulation was observed for the two type of tumors. Conclusion: $[^{18}F]FHBG$ appears to be a useful as non-invasive PET imaging substrate in HSV1-tk expressing hepatoma model.