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Wavelength‐Dependent Efficiency of Sequential Photooxygenation: C=C Bond Cleavage on Open‐Cage C 60 Derivatives
Author(s) -
Hashikawa Yoshifumi,
Murata Yasujiro
Publication year - 2018
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800464
Subject(s) - photooxygenation , cage , bond cleavage , chemistry , photochemistry , wavelength , cleavage (geology) , triple bond , materials science , optoelectronics , double bond , polymer chemistry , organic chemistry , singlet oxygen , catalysis , mathematics , combinatorics , composite material , fracture (geology) , oxygen
We have studied the efficiency of the C=C double bond cleavage on open‐cage fullerene C 60 derivatives by singlet oxygen using four different LED lamps including UV, blue, green, and red radiation. The results indicate that red radiation is the most efficient for this photochemical oxidation owing to the sufficient penetration of the longer‐wavelength light. By applying this method to a 2‐methoxyethoxymethyl‐substituted azafulleroid derivative, we demonstrated the sequential double photooxygenation which provides a symmetric diketo imide derivative having a 15‐membered‐ring opening via stepwise cleavage of two C=C double bonds. Using a H 2 ‐encapsulating derivative, we further examined the size of the opening by comparison with the structural isomer, based on H 2 ‐release experiments and theoretical calculations.