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Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study
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  • Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study
  • Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study
저자명
Nourmohammadian. Farahnaz,Abdi. Ali Ashtiani
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2013년|34권 6호|pp.1727-1734 (8 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

Synthesis and characterization of some novel symmetric bis-azospiropyrans are reported in this study. These bis-azospiropyrans are bifunctional chromophores with two spiropyrans linked by a bis-azo extended aromatic system that produce more color strength (large molar absorption coefficient in mero forms) due to appending two azospiropyran chromophores on one molecule. Comparing to the molar absorption coefficients of the conventional spiropyran chromophores (${varepsilon}=0.31{ imes}10^4;M^{-1}{cdot}cm^{-1}$) and mono-azospiropyran chromophores ($1.35{ imes}10^4;M^{-1}{cdot}cm^{-1}$), the novel synthesized photochromes showed astonishingly increased molar absorption coefficients ($2.3-3.8{ imes}10^4;M^{-1}{cdot}cm^{-1}$) at the same conditions. Such high molar absorption coefficients confers high sensitivity to light and more color intensity of mero form, that leads to improvement of their light sensitivity and better discrimination of spiro (OFF) form from mero (ON) ones in molecular switches. The structures were deduced from their MS, FT-IR, and $^1H$-NMR spectroscopic data and CHN analysis. All the synthesized photochemically bifunctional compounds revealed fluorescent emission in their colorless form which was faded out after exposing to UV light. Fluorescence quantum yield values of the mero forms were 0.25-0.81 and two high fluorescence quantum yield values (0.60 and 0.81) were found in these series.