[Synthesis and optical properties of the helical oligonaphthalenes].
We have developed an efficient synthesis method for optically active oligonaphthalenes (from 2 mer to 16 mer), which are connected at their 1,4-positions, under oxidative homo coupling with a stoichiometric amount of CuCl(2) and amines. The absolute configuration of the newly formed axis bond was determined based on the CD spectra of oligonaphthalenes with 1) two pyrene rings on the central naphthalenes or 2) two tetraphenylporphyrins (TPP) on the top and bottom naphthalenes. The fluorescence quantum yields increased as the number of naphthalene units increased in methoxy derivatives 10-12, and the intramolecular energy transfer quantum yields of bispyrene derivatives 7-9 were around 20% regardless of the number of naphthalene units. Furthermore, the hexadecanaphthalene derivative 4b with two TPPs exhibited a clear exciton coupling over an interchromophore distance to ca. 66 A.
Takaishi
Kazuto
K
Institute for Chemical Research, Kyoto University, Japan. takaishi@fos.kuicr.kyoto-u.ac.jp
Tsubaki
Kazunori
K
Tanaka
Hiroyuki
H
Miura
Masaya
M
Kawabata
Takeo
T
D000588:Amines; D002625:Chemistry, Organic; D003300:Copper; D004735:Energy Transfer; D008027:Light; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014466:Ultraviolet Rays
D000588:Amines; D009281:Naphthalenes; D003300:Copper; C028419:cuprous chloride