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Soluble and Planar 2,9‐Diazaperopyrenes through Reductive Aromatization of Perylene Diimides: Tunable Emission and Aggregation Behaviors
Author(s) -
Nakamura Yasutaka,
Nakazato Takumi,
Kamatsuka Takuto,
Shinokubo Hiroshi,
Miyake Yoshihiro
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902123
Subject(s) - perylene , aromatization , aryl , chemistry , photochemistry , nickel , planar , catalysis , organic chemistry , molecule , alkyl , computer graphics (images) , computer science
Reductive aromatization of perylene diimides with acid anhydrides in the presence of Mn or Zn metals provides soluble and planar 2,9‐diazaperopyrenes with ester groups at 1,3,8,10‐positions. The pivaloxy groups at the peripheral positions can be transformed into a variety of aryl groups through nickel‐catalyzed cross‐coupling of ester groups. Emission colors of diazaperopyrenes are tunable by the peripheral substituents. The peripheral substituents also affect the aggregation behaviors of 2,9‐diazaperopyrenes in the solution and solid states.