Abstract
Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.
| Original language | English |
|---|---|
| Pages (from-to) | 276-279 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 6 2012 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Takaishi, K., Muranaka, A., Kawamoto, M., & Uchiyama, M. (2012). Photoinversion of cisoid/transoid binaphthyls. Organic Letters, 14(1), 276-279. https://doi.org/10.1021/ol203053q