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Spiroindolinonaphthoxazine 색소의 합성과 광물리적 성질에 관한 연구

A Study on Syntheses and Photophysical Properties of Spiroindolinonaphthoxazine Dye

HWAHAK KONGHAK, August 1995, 33(4), 497-502(6), NONE
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Abstract

광변색성 spiroindolinonaphthoxazine 색소를 1,3,3-trimethyl-2-methylene indoline 과 1-nitroso-2
-naphthol의 축합반응으로 합성하였다. 합성한 생성물을 TLC, 융점측정, UV, IR, 1H-NMR, 13C-NMR 및 원소분석으로 확인하였다. Spiroindolinonaphthoxazine의 광물리적 성질을 자외선-가시광선 분광계로 조사하였다. 에탄올 용액에서 소색체와 발색체는 각각 고유의 특성밴드들을 보였다. 소색체와 발색체 사이에 열적 평형이 존재하며, 다른 온도들에서의 발색체의 흡수스펙트럼으로부터 열적 평형반응의 표준엔탈피를 구하였다. Spiroindolinonaphtoxazine 수율의 향상을 위항 여러 촉매를 사용하여 접촉축합반응을 시도하였다. 5wt% Pd/C 촉매에서 무촉매 축합반응보다 약 2배의 수율을 얻었는데, 이 결과는 촉매공정에 의하여 spiroindolinonaphthoxazine 수율을 증대시킬 수 있음을 시사한다.
Photochromic spiroindolinonaphthoxazine dye was synthesized via condensation of 1,3,3-trimethyl-2-methylene indoline with 1-nitroso-2-naphthol. Spiroindolinonaphtoxazine prepared was characterized by means of TLC, melting point measurement, UV, IR, 1H-NMR, 13C-NMR, 13C-NMR, and elemental analysis. Photophysical properties of spiroindolinonaphthoxazine were investigated using UV-visible spectrophotometer. The color-less form and the colored metastable form in ethanol solution exhibited unique characteristic bands respectively. A thermal equilibrium existed between the colorless and colored forms, and the standard enthalpy of equilibrium could be obtained from the measurement of absorbance of the colored form at different temperatures. Catalytic condensation reactions were conducted on various catalysts in order to improve the yield of spiroindolinonaphthoxazine. 5wt% Pd/C catalyst resulted in the yield about two times higher then that for nonanalytic condensation. which suggests the possibility of improvement in spiroindolinonaphthoxazine yield by the catalytic process.

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References

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