Helicity‐Dependent Regiodifferentiation in the Excited‐State Quenching and Chiroptical Properties of Inward/Outward Helical Coumarins
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- Arindam Mukhopadhyay
- Department of Chemistry Indian Institute of Technology Kanpur 208016 India
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- Tousif Hossen
- Department of Chemistry Indian Institute of Technology Guwahati 781039 India
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- Indrajit Ghosh
- Department of Life Sciences and Chemistry Jacobs University Bremen Campus Ring 1 28759 Bremen Germany
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- Apurba Lal Koner
- Department of Chemistry Indian Institute of Science Education and Research Bhopal 462066 India
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- Werner M. Nau
- Department of Life Sciences and Chemistry Jacobs University Bremen Campus Ring 1 28759 Bremen Germany
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- Kalyanasis Sahu
- Department of Chemistry Indian Institute of Technology Guwahati 781039 India
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- Jarugu Narasimha Moorthy
- Department of Chemistry Indian Institute of Technology Kanpur 208016 India
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説明
<jats:title>Abstract</jats:title><jats:p>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⋅⋅⋅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 <jats:bold>6‐<jats:italic>in</jats:italic></jats:bold> turns out being the highest of the values reported for all hexahelicenes reported so far.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 23 (59), 14797-14805, 2017-09-21
Wiley
