Atropisomers of meso-conjugated uracyl porphyrin derivatives and their assembling structures

Satoshi Arai; Daisuke Niwa; Hiroyuki Nishide; Shinji Takeoka

doi:10.1021/ol062394q

Atropisomers of meso-conjugated uracyl porphyrin derivatives and their assembling structures

Satoshi Arai, Daisuke Niwa, Hiroyuki Nishide, Shinji Takeoka^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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 αα isomer formed a face-to-face dimer, whereas the αβ isomer took a zigzag structure.

Original language	English
Pages (from-to)	17-20
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	1
DOIs	https://doi.org/10.1021/ol062394q
Publication status	Published - 2007 Jan 4

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062394q

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abstract = "(Chemical Equation Presented) 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 αα isomer formed a face-to-face dimer, whereas the αβ isomer took a zigzag structure.",

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AU - Nishide, Hiroyuki

AU - Takeoka, Shinji

PY - 2007/1/4

Y1 - 2007/1/4

N2 - (Chemical Equation Presented) 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 αα isomer formed a face-to-face dimer, whereas the αβ isomer took a zigzag structure.

AB - (Chemical Equation Presented) 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 αα isomer formed a face-to-face dimer, whereas the αβ isomer took a zigzag structure.

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Atropisomers of meso-conjugated uracyl porphyrin derivatives and their assembling structures

Abstract

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