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 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Photoinversion of cisoid/transoid binaphthyls. / Takaishi, Kazuto; Muranaka, Atsuya; Kawamoto, Masuki; Uchiyama, Masanobu.
In: Organic Letters, Vol. 14, No. 1, 06.01.2012, p. 276-279.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Photoinversion of cisoid/transoid binaphthyls
AU - Takaishi, Kazuto
AU - Muranaka, Atsuya
AU - Kawamoto, Masuki
AU - Uchiyama, Masanobu
PY - 2012/1/6
Y1 - 2012/1/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84855472746&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84855472746&partnerID=8YFLogxK
U2 - 10.1021/ol203053q
DO - 10.1021/ol203053q
M3 - Article
C2 - 22148882
AN - SCOPUS:84855472746
VL - 14
SP - 276
EP - 279
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 1
ER -