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One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated Perylene
Author(s) -
Fujita Ryuichi,
Hirakawa Miho,
Oyama Ryoko,
Matsuo Kyohei,
Hayashi Hironobu,
Yamauchi Mitsuaki,
Yamada Hiroko,
Aratani Naoki
Publication year - 2025
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202500042
Subject(s) - perylene , chemistry , dimer , one step , two step , organic chemistry , photochemistry , combinatorial chemistry , molecule , chemical engineering , engineering
Abstract One‐step Suzuki‐Miyaura cross‐coupling reaction of 2,5,8,11‐tetra‐borylated perylene with 2,6‐bis(trifluoromethyl)bromo‐benzene gave 2,2’‐linked perylene dimer for the first time in 7.3 % yield under the standard conditions. The single‐crystal X‐ray structure exhibits three independent dimers in the unit cell, reflecting the low rotational energy around 2,2’‐linkage. Excited state properties of 2,2’‐dimer were compared with the corresponding 3,3’‐linked congener. The facile synthetic method developed in this study could be a general route to access polycyclic aromatic hydrocarbon oligomers linked at less reactive positions.

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