Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 13, Pages 5254-5258Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914414
Keywords
circularly polarized luminescence; conformational transformations; cyclophanes; naphthalenediimide dimers; optical thermometry
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Funding
- KAKENHI from JSPS [26102009]
- MEXT NIMS Molecule and Material Synthesis Platform program
- NIMS
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The design and synthesis of an enantiomeric pair of 1,8-diethynylanthracene-bridged naphthalenediimide (NDI)-based cyclophanes (Cyclo-NDIs) are reported. Each enantiomer of Cyclo-NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (g(lum)=+/- 8x10(-3)). We have further investigated the modulation of through-space electronic communication between co-facially oriented NDIs in a discrete Cyclo-NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer- versus dimer-like features of Cyclo-NDI, as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature-dependent optical response in the Cyclo-NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to -80 degrees C).
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