Atropisomers of meso-conjugated uracyl porphyrin derivatives and their assembling structures.
[reaction: see text] We have synthesized a 5,15 meso-substituted methyluracyl porphyrin derivative bearing 6-methyluracyl units directly at the meso positions. The atropisomerization was regulated by steric replusion between the methyl substituents. When the atropisomers were mixed with alkylated melamine as a complementary hydrogen-bonding unit, the hydrogen-bonded assemblies were analyzed by diffusion-ordered spectroscopy (DOSY) in solution, which clarified that the alphabeta isomer formed a face-to-face dimer, whereas the alphabeta isomer took a zigzag structure.
Arai
Satoshi
S
Department of Applied Chemistry, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
Niwa
Daisuke
D
Nishide
Hiroyuki
H
Takeoka
Shinji
S
D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry; D014025:Titanium / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D011166:Porphyrins; D013440:Sulfides; D014498:Uracil; C093850:methylphenylsulfide; D006861:Hydrogen Peroxide; D014025:Titanium