期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 59, 页码 14797-14805出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701787
关键词
circular dichroism; electron transfer; fluorescence; helicenes; hydrogen bonds
资金
- Science and Engineering Research Board (SERB), New Delhi [SB/S2/JCB-52/2014]
- Alexander von Humboldt Foundation, Germany
- Council of Scientific and Industrial Research (CSIR), New Delhi
Influence of helicity on the excited-state as well as chiroptical properties of two sets of regiohelical coumarins that are differentiated by inward and outward disposition of the pyran-2-one ring has been investigated. A subtle difference in the helicities manifests in divergent excited-state properties and significant differences in the dipole moments. The latter permit heretofore unprecedented regiodifferentiation in the O-H center dot center dot center dot O hydrogen-bond assisted electron-transfer quenching by phenols. Furthermore, the enantiopure hexahelical coumarins exhibit strong Cotton effects and lend themselves to a very high differentiation in the specific rotations and anisotropic dissymmetry factors. The specific rotation observed for 6-in turns out being the highest of the values reported for all hexahelicenes reported so far.
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