Intramolecular Chirality Transfer in trans-5,6-Diaryl-5,6-dihydro-1,10-phenanthroline-5,6-diols: Solvato- and Halochromic Responses by Circular Dichroism

Not only the configuration at the C5 and C6 stereocenters but also the intra/intermoleculer hydrogen-bonding mode are determinant for the sense of mobile helicity of the dihydrophenanthroline unit in the title diols in solution. Thus, drastic changes in chiroptical signals are induced through confor...

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Bibliographic Details
Published inChemistry letters Vol. 39; no. 7; pp. 695 - 697
Main Authors Suzuki, Takanori, Miura, Youhei, Nehira, Tatsuo, Kawai, Hidetoshi, Fujiwara, Kenshu
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.07.2010
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
AXIAL CHIRALITY
POINT CHIRALITY
ELECTROCHIROPTICAL RESPONSE
DYNAMIC REDOX BEHAVIOR
SPECTRAL CHANGES
STRONG CHIROPTICAL SIGNALS
ELECTRON-DONORS
BIPHENYL CORE
HYDROGEN-BONDS
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Summary:Not only the configuration at the C5 and C6 stereocenters but also the intra/intermoleculer hydrogen-bonding mode are determinant for the sense of mobile helicity of the dihydrophenanthroline unit in the title diols in solution. Thus, drastic changes in chiroptical signals are induced through conformational switching of 1 upon addition of protic solvent and/or acid.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2010.695