• Journal of Photoscience
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• v.4 no.2
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• pp.49-52
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• 1997

Irradiation (300 nm) of 1, 2-benzoquinones 1 and diphenylacetylene 2 in dichloromethane yielded two isomeric quinone methides, 6 and 7. The same types of quinone methides, 9 and 10 (or 12 and 13) were obtained from the photocycloadditions of 9, 10-phenanthrenequinone 8 (or acenaphthenequinone 11) to diphenylacetylene 2. One-way photoisomerizations were observed between each isomeric adducts, (6, 7), (9, 10) and (12, 13).

• Bulletin of the Korean Chemical Society
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• v.10 no.1
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• pp.57-60
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• 1989

UV irradiation of anthraquinone and diphenylacetylene in benzene gave 1:1 photoadduct (7) and cyclization product (8). The photoreaction of anthrone and diphenylacetylene in dichloromethane afforded the photooxidation products (7, 8, and 9) in air. The photoproduct (7) underwent the cyclization reaction during the purification by the column chromatography (silica gel). When irradiated with 350 nm UV light, the product (11) of benzil reacted with diphenylacetylene to give a photoadduct(12).

• Bulletin of the Korean Chemical Society
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• v.19 no.12
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• pp.1295-1297
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• 1998

• Bulletin of the Korean Chemical Society
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• v.15 no.12
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• pp.1124-1126
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• 1994

• Journal of the Korean Chemical Society
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• v.37 no.8
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• pp.757-764
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• 1993

The photochemical precursors, 1,1,1,3,3,3-hexamethyl-2-phenyltrisilane(2) and 2,3-dicarbomethoxy-1,4,5,6,7-pentaphenyl-7-silanorbornadiene(5) were synthesized in the yield of 10% and 73%, respectively. Irradiation of 2 at 254 nm in the presence of triethylsilane gave 1,1,1-triethyl-2-phenyldisilane (6) in 44% yield which was the product of phenylsilylene insertion into the Si-H bond. Irradiation of 2 in the presence of diphenylacetylene gave 1-phenyl-1-silacyclopenta-2,4-diene(4) in 68% yield together with 1,2-diphenyl-1,2-disilacyclohexa-2,5-diene(26%) which were formed from [2＋2] addition of the silacyclopropene to diphenylacethylene and formed from dimerization of silacyclopropene, respectively. From the neat photolysis of precursor 2,1,5-dihydrosilanthrene(11), intermolecular C-H insertion product of phenylsilylene and 1,2-diphenyltrisilane(12), Si-H insertion product of phenylsilylene to the precursor were obtained in the yield of 5% and 7%, respectively. In the same experimental condition, both photolyses of 5 in the presence of triethylsilane and methanol showed that the intramolecular 1,5-sigmatropic rearrangement of precursor 5 to give the formation of silylenolether was more favorable process than the generation of phenylsilylene.

• Analytical Science and Technology
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• v.31 no.5
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• pp.179-184
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• 2018

Diphencyprone (DPCP) is frequently used as a compounded preparation in dermatology for the treatment of alopecia and recalcitrant warts based on the immune reaction of skin allergy. However, DPCP is a non-recognized agent in Pharmacopoeia, because there are no criteria or analytical method for quality control of its powder and formulation. DPCP is unstable under light irradiation because as it easily decomposes to diphenylacetylene (DPA). This study aims to develop a simultaneous HPLC analytical method for analyzing DPCP and DPA in the raw materials and compounded preparation. The method required a C18 column ($250{\times}4.6mm$, $5{\mu}m$) at $40^{\circ}C$ with a mobile phase of (A) 0.01 M phosphoric acid in water and (B) acetonitrile at UV 220 nm. DPA conversion to DPCP in the powder and compounded preparations was accelerated after light exposure for 60 min. In addition, this resulted in different patterns depending on the wavelength of light and the formulation. That is, DPCP in compounded preparation was more unstable than that in the powder. However, the DPCP formulation in amber bottles was observed to remain stable, although the measured concentrations of DPCP were somewhat different from the nominal concentration of the compounded preparations. The control of the exact concentration is required for effective disease treatment, depending on the state of the patient. In conclusion, these results will be useful for the recognition of DPCP in Pharmacopoeia and new DPCP formulation development to prevent photodecomposition.

• Journal of Photoscience
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• v.5 no.4
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• pp.143-148
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• 1998

Photoaddition reactions of ο-benzoquinones to some organic molecules were ivestigated to yield three types of photoadducts. Irradiation (350nm UV light) of a dichloromethane solution of tetrahal-1, 2- benzoquinones and 1, 4-diphenylbutadiene yielded 1, 3-dienes, which was found to be used to synthesize 1-phenylphenanthrenes. The 1, 3-dienes were also produced, when irradiated tetrahalo--1, 2-benzoquinones and 1,4-dipenylbut-1-en-3-yne in the similar conditions, which was applied to get 9-phenylphenanthrenes. An enolic compound come from the tautomerization of dibenzoylmethane was found to add to ο-benzoquinones to give, 1, 4-dioxenes and 1, 5-diketones as the major products. Although depenylbutadiyne did not add to ο-benzoquinones, diphenylacetylene added to ο-benzoquinones to give $\rho$-quinomethanes as well as two isomeric $\rho$-quinomethanes. One-way photoisomerism was observed for two isomeric $\rho$-quinomethanes.

• Proceedings of the Korean Vacuum Society Conference
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• 2014.02a
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• pp.125-125
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• 2014

In 1991, Prof. Toshio Masuda of Kyoto University for the first time synthesized a representative of diphenylacetylene polymer derivatives, poly[1-phenyl-2-(p-trimethylsilyl)phenylacetylene] [PTMSDPA]. This polymer is highly soluble nevertheless a ultra-high molecular weight (Mw) of > $1.0{\times}10^6$ which showed excellent chemical, physical, mechanical properties [1]. As one of the most interesting features of PTMSDPA, Prof. Katsumi Yoshino of Osaka Univ. reported that this polymer emits an intense fluorescence (FL) in a visible region because of the effective exciton confinement within the resonant structure between the polyene pi-conjugated chain and side phenyl full-aromatic bulky groups [2]. Very recently, Prof. Ben-Zhong Tang of Hong-Kong Institute of Science and Technology clarified the idea that the FL emission of disubstituted acetylene polymer derivatives originates from intramolecular excimer due to the face-to-face stacking of the side phenyl groups [3]. Thus, to know what influence to intramolecular excimer emission in the film as well as to further understand how the intramolecular excimer forms in the film became more crucial in order to further precisely design the optimized molecular structure for highly emissive, substituted acetylene polymers in the solid state. In recent studies, we have focused our interests on the origin of the FL emission in order to expand our knowledge to developments of novel sensor applications. It was found that the intramolecular phenyl-pheyl stack structure of PTMSDPA in film was variable in response to various external chemical stimuli. Using PTMSDPA and its derivatives, we have developed various potential applications such as latent fingerprint identification, viscosity sensor, chemical-responsive actuator, gum-like soft conjugated polymer, and bioimaging. The details will be presented in the 49th KVS Symposium held in Pyong Chang city.