Formation of cubane-like photodimers from 2-naphthalenecarbonitrile.
Irradiation of 2-naphthalenecarbonitrile (2-NpCN) in solution with a light lambda > 280 nm results in the formation of three rigid cubane-like photodimers, anti-head-to-head 1, anti-head-to-tail 2, and syn-head-to-tail 3, which are not in line with the previously recognized regioselectivity. These cubane-like photodimers have been well characterized by spectroscopic investigation and/or X-ray crystal structural analysis in this work. Moreover, the separation of the optically pure enantiomers of 1, 2, and 3 has been achieved by HPLC resolution.
Liao
Gui-Hong
GH
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, the Chinese Academy of Sciences, Beijing 100190, People's Republic of China.
Luo
Lin
L
Xu
Hong-Xia
HX
Wu
Xiao-Ling
XL
Lei
Lei
L
Tung
Chen-Ho
CH
Wu
Li-Zhu
LZ
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D003500:Cyclization; D019281:Dimerization; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000528:radiation effects*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D010777:Photochemistry; D013237:Stereoisomerism; D014466:Ultraviolet Rays
D009281:Naphthalenes; D009570:Nitriles; C532787:2-naphthalenecarbonitrile