期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 37, 页码 9434-9441出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900968
关键词
chirality; fluorescence; molecular response systems; redox chemistry; solvatochromism
资金
- MEXT
- Hokkaido University
3,3,4,4-Tetaaryldihydro[5]helicenes (1) and 1,1'-binaphthyl-2,2'-diyl-bis(diarylcarbenium)s (2(2+)) can be reversibly interconverted upon electron transfer, which is accompanied by a vivid color change (electrochromism) as well as by the formation/cleavage of a C-C bond (dynamic redox behavior). Because only the neutral donor 1 exhibits strong fluorescence, electrochemical input can further modify the fluorescent properties of the pair. Due to the configurational stability of the helicity in 1 and axial chirality in 2(2+), the redox reaction of optically pure material proceeds stereospecifically, which induces a chiroptical change such as circular dichroism (CD) as an additional output. The CD spectra of dications 2(2+) exhibit solvent dependency (chiro-solvatochromism), which is accompanied by solvatochromic behavior based on the pi-pi interaction of the two cationic chromophores as well as coordinative interaction of the Lewis basic solvent to the Lewis acidic triarylcarbenium moieties. Thus, the present system is endowed with multi-input functionality for modifying multiple output signals.
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