One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated Perylene
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.
Authors
- Ryoko Oyama (ORCID: https://orcid.org/0000-0001-9289-0837)
- Hiroko Yamada (ORCID: https://orcid.org/0000-0002-2138-5902)
- Mitsuaki Yamauchi (ORCID: https://orcid.org/0000-0003-0005-5960)
- Naoki Aratani (ORCID: https://orcid.org/0000-0002-3181-6526)
- Hironobu Hayashi (ORCID: https://orcid.org/0000-0002-7872-3052)
- Kyohei Matsuo (ORCID: https://orcid.org/0000-0002-2472-9459)
- Ryuichi Fujita
- M. Hirakawa
Institutions
- National Institute for Materials Science (JP)
- Kyoto University (JP)
- Kyoto Bunkyo University (JP)
- Instituto de Investigaciones Químicas (ES)
- National Institute for Mathematical Sciences (KR)
- Nara Institute of Science and Technology (JP)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2025-02-21
- DOI
- https://doi.org/10.1002/ejoc.202500042
- Citations
- 1
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Japan Society for the Promotion of Science