Deboronation-induced ratiometric emission sensing of fluoride by 1,3,5-tris-(o-carboranyl-methyl)benzene |
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| Authors: | Dong Kyun You Ji Hye Lee Hyonseok Hwang Hyoshik Kwon Myung Hwan Park Kang Mun Lee |
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| Affiliation: | 1. Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University, Chuncheon, Gangwon 24341, Republic of Korea;2. Department of Chemistry Education, Chungbuk National University, Cheongju, Chungbuk 28644, Republic of Korea |
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| Abstract: | 1,3,5-Tris-(o-carboranyl-methyl)benzene (closo-1) and its nido-form (nido-1) were synthesized and fully characterized. The solid-state molecular structure of closo-1 was determined by single-crystal X-ray diffraction analysis. Compound closo-1 exhibited an intense single emission in various organic solvents that was red-shifted with increasing solvent polarity. The positive solvatochromic effect and theoretical calculation results at the first excited (S1) optimized structure of closo-1 strongly suggest that this emissive band can be assigned to an intramolecular charge transfer. Meanwhile, nido-1 showed a pronounced red-shift of the emissive band compared to that of closo-1 and aroused low-energy emission. The specific emissive features of nido-1 were attributed to the elevation of its HOMO level, estimated by cyclic voltammetry. The photophysical changes by conversion from closo-1 to nido-1 allowed the emissive color-tunable sensing of fluoride. Thus, the tris-o-carboranyl compound showed great potential as a chemodosimeter for fluoride anion sensing, detectable by the naked-eye. |
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| Keywords: | Fluoride Color change |
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