• Journal of the Korean Chemical Society
• /
• v.39 no.5
• /
• pp.329-337
• /
• 1995

Energetic oxetane derivatives which undergo cationic polymerizations have been investigated theoretically by using ab initio HF/3-21G calculations. We have examined structures, charges, and molecular electrostatic potentials. The ring structure of oxetane has changed significantly due to (1) the introduction of large substituents in the ring or (2) the addition of either proton or BF3. This structural change is attributed to electrostatic interactions and/or steric repulsions. The nucleophilicity and basicity of oxetane derivatives can be explained by the negative charge and the minimum electrostatic potential value of O atom. The reactivity in the polymerization can be rationalized by (1) the basicity of O atom and (2) the difference between HOMO energy of oxetanes and LUMO energy of activated oxetane polymeric chains. Our calculations predict that 3-azidomethyl-3-methyl oxetane (AMMO) is more basic than 3-nitratomethyl-3-methyl oxetane (NMMO), and AMMO is more reactive toward both AMMO and NMMO polymeric chains. Our results are in good agreement with previous experimental data.

• Proceedings of the Polymer Society of Korea Conference
• /
• 2006.10a
• /
• pp.104-105
• /
• 2006

We succeeded the synthesis of new functional polymers by novel ring-opening addition reactions of bis(oxetane)s with diacyl chlorides, di(active ester)s, and di(carboxylic acid)s using quaternary onium salts as catalysts at appropriate conditions. Hyperbranched polyesters with many pendant hydroxy groups were also synthesized by the polyaddition of bis(oxetane)s with tricarboxylic acid, or by the self-polyadditions of $AB_2\;or\;A_2B$ type monomers containing oxetane group. The anionic ring-opening polymerization of (3-ethyl-3-hydroxymethyl)oxetane was examined using sodium tert-buthoxide to give hyperbranched poly(ether)s containing one oxetanyl group and many hydroxyl groups in the end of polymer chain.

• Applied Chemistry for Engineering
• /
• v.20 no.2
• /
• pp.159-164
• /
• 2009

Monomers of oxetane high explosives were theoretically examined in terms of reactivity, reaction mechanism and process of polymerization substituted by azido $(-CH_2N_3)$, nitrato $(-CH_2ONO_2)$ and hydrazino $(-CH_2N_2H_3)$ which belong to the 5th class hazardous materials and have explosiveness under acid catalyst using MINDO/3, MNDO, and AMI methods for formal charge, heat of formation, and energy level. Nucleophilicity and base of oxetane high explosives could be explained by negative charge size of oxetane oxygen atom and reactivity of oxetane in the growth stage of polymerization under acid catalyzer could be expected to be governed by positive charge size of axial carbon atom and low LUMO energy of electrophile. It could be estimated that carbenium ion was more beneficial in the conversion process of oxetane high explosives than that of stabilization energy (13.90~31.02 kcal/mole) of oxonium ion. In addition, concentration of oxonium ion and carbenium ion in equilibrium state influenced mechanism and it was also estimated that $S_N1$ mechanism reacts faster than that of $S_N2$ in prepolymer growth stage considering quick equilibrium based on form and calculation of polymerization under acid catalyzer.

• 한국정보디스플레이학회:학술대회논문집
• /
• 2005.07b
• /
• pp.1419-1420
• /
• 2005

We have synthesized a photo patternable blue lightemitting polyfluorene (PF) derivative containing cross-linkable oxetane units. Poly(9,9-bis-(4-octyloxyphenyl)- fluorene-2,7-diyl-alt-9,9-bis-((3-hexyloxy-3'- ethyl)-oxetane)-fluorene-2,7-diyl) has been synthesized by Suzuki coupling polymerization. The relationship between patterning property and several variables such as the intensity of the exposed UV light, the concentrations of additives, has been studied by using optical microscope UV/visible spectroscopy, photoluminescence and scanning electron microscope (SEM). We obtained fine patterns with 10 mm resolution using the polymer film after exposure and development. This patterning method using conjugated polymers can be applicable to make fine pixels for PLEDs and OFETs.

• Bulletin of the Korean Chemical Society
• /
• v.15 no.11
• /
• pp.928-930
• /
• 1994

• Journal of the Korean Chemical Society
• /
• v.37 no.6
• /
• pp.626-632
• /
• 1993

Oxetane derivatives (AMMO, BAMO, NMMO, BNMO) having energetic substituents were synthesized and characterized in order to improve the production yield and practical scale-up.

• Bulletin of the Korean Chemical Society
• /
• v.31 no.11
• /
• pp.3431-3433
• /
• 2010

• Proceedings of the Optical Society of Korea Conference
• /
• 2004.02a
• /
• pp.134-135
• /
• 2004

• Archives of Pharmacal Research
• /
• v.8 no.1
• /
• pp.39-41
• /
• 1985

Bromocycloetherification of a series of 3-and 4-olefinic alcohols using NBS-acetonitrile gave corresponding bromo-tetrahydrofuran with high regio and steroselectivity.

• Bulletin of the Korean Chemical Society
• /
• v.20 no.5
• /
• pp.531-534
• /
• 1999

Irradiation (300 nm UV light) of dibenzoylmethane and 1,4-naphthoquinone in dichloromethane gave 1,5-dike-tone as the major product, along with β-hydroxyketone as the minor product. Anthraquinone and anthrone also added photochemically to dibenzoylmethane to give 1,5-diketones as the major products. In contrast, tetrahalo-1,4-benzoquinones added to dibenzoylmethane to give two types of 1,5-diketones via oxetane and cyclobutane intermediates. Comparison of the potential energy values of the photoproducts reveals that the 1,5-diketones are more stable than the corresponding oxetanes or cyclobutanes due to the ring-strain of the bicyclic compounds.