• Clean Technology
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• v.17 no.4
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• pp.325-328
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• 2011

Atom-efficient preparation of 9, 9'-bis[4-(2'-hydroxy-3'-acryloyloxypropoxy) phenyl]fluorene (3), the extensively used building block for fluorene-containing acrylic epoxy polymers has been described. The epoxide ring opening esterification of 9, 9-bis[4-(glycidyloxy)phenyl]fluorene (1) with acrylic acid was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts. While the coupling reactions depend greatly on the kind of the onium salts, the reaction of 9, 9-bis[4-(glycidyloxy)phenyl]fluorene (1) with acrylic acid proceed most efficiently in the presence of a catalytic amount of tetrabutylphosphonium bromide at $110^{\circ}C$ with 90% yield. This reaction is a cleaner reaction that minimizes the use of reactants and the production of chemical wastes.

• Clean Technology
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• v.18 no.3
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• pp.325-328
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• 2012

The condensation reaction of 9,9'-bis(4-hydroxyphenyl)fluorene with epichlorohydrin to prepare 9,9'-bis[4(glycidyloxy) phenyl]fluorene (2), an important building block for fluorene-containing epoxy polymers, has been studied. The reaction is found to be quite sensitive to several experimental conditions such as reaction temperature and time, added amount of epichlorohydrin, the presence of catalysts and the use of co-solvent. Several conditions for obtaining the best yield in the reaction are: the reaction temperature is below 373 K and the reaction time is shorter than 1.5 h, and the ammonium salts act as a catalyst. Also, the use of ternary solvent (toluene, DMSO, water) has been proved to be crucial to maintain the reaction temperature and for an easy purification. Thus, the reaction proceeds in an environment-friendly manner where the use of reactants and the production of chemical wastes is minimized.

• Proceedings of the Korean Environmental Sciences Society Conference
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• 2016.10a
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• pp.146-146
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• 2016

• Journal of Environmental Health Sciences
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• v.37 no.2
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• pp.159-164
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• 2011

We describe a method for effectively pretreating soil highly that has been contaminated with fluorene (${\gg}$ 120 mg/kg soil), i.e., we apply Fenton oxidation in which ethanol is added to increase fluorene removal. To obtain maximum fluorene removal efficiency, a minimum of 1.0 ml of ethanol, 0.35 ml of $H_2O_2$, and 0.2 ml of 0.5M $Fe^{2+}$ was needed per 1 g of fluorene-contaminated soil. Under optimal Fenton oxidation conditions, 13% of 9-fluorene was generated during Fenton oxidation of 43% fluorene. The biodegradability of 9-fluorenone was subsequently confirmed to be much more rapid than that of fluorene, i.e., biodegradability of 96% versus 35% over 31 days. These results demonstrate that the proposed treatment method can be effectively applied to remove fluorene prior to disposal at industrial waste sites.

• Polymer(Korea)
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• v.25 no.3
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• pp.327-333
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• 2001

Acetylene substituted fluorenes such as 2-ethynylfluorene and 2,7-diethynyl-fluorene were synthesized and thin films were prepared by the vacuum deposition. Curing of these fluorene derivatives could be achieved by heat treatment and UV irradiation. The curing temperature of 2-ethynylfluorene and 2,7-diethynylfluorene were found to be 231 and $198^{\circ}C$, respectively. The cured poly(2-ethynylfluorene) and poly(2,7-diethynylfluorene) started to decompose at 280 and $ 385^{\circ}C$, respectively. Fluorescent characteristics of the cured films were similar to those of monomers, but fluorescent efficiency of the film was decreased about 3 to 10 fold.

• Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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• 2008.06a
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• pp.465-465
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• 2008

Conjugated polymers have attracted much scientific and technological research interest during the past few decades because of their potential use such as polymer light-emitting diodes (PLEDs).1,2 Particularly, lots of phenylene-based polymers such as polyfluorene and its derivatives have been synthesized because of their high photoluminescence quantum efficiencies and thermal stabilities. However, troublesome long wavelength emission in polymer film of polyfluorenes on heating during device formation or operation has been the crucial problem for practical applications. The source of the long wavelength emission was initially believed to be solely due to excimer emission as a result of polymer aggregation. It has also recently been correlated with emissions from ketonic defects in the fluorene units. Many efforts have been made to reduce the tendency to red-shifted emission. Here, we report for the first time the design and synthesis of novel 9,9-spiro bifluornene-based polymers containing heteroatoms such as N, S in its molecular skeleton. Especially, the 9,9-spiro bifluornene-based polymers containing N atom showed stable blue electroluminescence, which did not show spectral change upon thermal annealing.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.23 no.7
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• pp.539-544
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• 2010

We have synthesized new blue electroluminescent polyalkylfluorene-based copolymers [poly(F-co-Py)x:y, where x:y = 99:1 or 95:5 mole ratios] containing the hole-injecting pyrazole derivative [3,3'-(4,6-bis(octyloxy)-1,3-phenylene)bis(1,5-diphenyl-4,5-dihydro-1H-pyrazole] through Ni(0) mediated polymerization, and their electroluminescent properties were investigated. Electroluminescent (EL) devices were fabricated with ITO / PEDOT:PSS (110 nm) / copolymers or PF homopolymer (80 nm) / Ca (50 nm) / Al (200 nm) configuration. Each EL device constructed from the copolymer exhibited significantly enhanced brightness and efficiency compared with a device constructed from the PF homopolymer. The EL device constructed with poly(F-co-Py)99:1 exhibited the highest luminous efficiency and brightness (0.95 cd/A and $2,907\;cd/m^2$, respectively). The achieved luminous efficiency was an excellent result, providing almost a 4-fold improvement on the efficiency obtainable with the a PF homopolymer device. This enhanced efficiency of the copolymer devices results from their improved hole injection and more efficient charge carrier balance, which arises from the HOMO level (~5.83 eV) of the poly(F-co-Py)99:1 copolymer, which is higher than that of the PF homopolyme (~5.90 eV).

• Clean Technology
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• v.16 no.4
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• pp.239-244
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• 2010

The carboxylation of the fluorenyl epoxide with a spiro framework, 9,9'-Bis(4-oxiranylmethoxyphenyl) fluorine (2) was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts to produce the corresponding five-membered cyclic carbonate (3) in an efficient and environmentally benign fashion. The coupling reactions depend greatly on the kind of the halide anions and alkyl chain length of the onium salts. While the reaction was sensitive to the reaction temperature, the reaction trends suggest that the catalytic efficiency of the quaternary ammonium halides may correlate strongly with the melting points of the halides. The reactions using a catalytic amount (2 mol %) of quaternary ammonium bromide with an n-butyl chain at 75.9 bar of $CO_2$ and 393 K give the highest yield of the cyclic carbonate (92%).