期刊
CHEMICAL SCIENCE
卷 4, 期 2, 页码 612-621出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc21307a
关键词
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资金
- Natural Sciences and Engineering Research Council of Canada
Reactions of indigo-N,N'-diarylimine ('Nindigo') derivatives with BF3 center dot Et2O give mono-or bis-BF2 chelate complexes 2 or 3 respectively. The product distribution between 2 and 3 is sensitive to the auxiliary base and solvent. Although the bis-BF2 complexes 3 are isolable, they gradually decompose in solution to the corresponding mono-BF2 species 2; this process is accelerated by water. The instability of 3 is believed to be due to ring stain effects based on structural analyses of 2. Electrochemical studies of 2 reveal one quasi-reversible oxidation process and two irreversible reductions, whereas derivatives of 3 possess a reversible oxidation and two sequential reversible reductions. The electronic spectra of 2 and 3 contain intense (epsilon similar to 3 x 10(4) M-1 cm(-1)) long-wavelength absorptions near 650 nm and 750 nm respectively. Both series of compounds are weakly emissive in the near-infrared. Time-dependent DFT calculations reveal the electronic transitions to be pi-pi* in nature.
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