期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 10, 页码 2987-2995出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002671
关键词
azobenzene; macrocycles; molecular devices; photochromism; template synthesis
资金
- Swiss National Science foundation (SNSF)
- Fonds der Chemischen Industrie
We report an efficient synthesis of cyclotris[(E)-3'-(biphenyl-3-yldiazenyl)] compounds (CTBs). An unsubstituted CTB molecule is accessible in four steps in 10% yield overall, whereas a hexa(methoxymethyl ether) CTB analogue was prepared in nine steps (26% yield). The final macrocyclization step was accomplished in up to 80% yield by using a metal-template effect. Furthermore, the photochromic properties were investigated, and all four isomers were detected and characterized by NMR spectroscopy. A strong influence from the solvent and the irradiation wavelength on the switching process was observed. Irradiation in pyridine yielded the highest amount of the all-Z isomer in the photostationary state. For a full conversion to the all-E isomer, the reaction has to be heated to 45 degrees C. The isomerization to the all-E isomer is slow at room temperature, with a half-life time of the all-Z isomer of more than nine days in dimethyl sulfoxide (DMSO). Conditions were established to access each possible isomer as the major component in the photostationary state.
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