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Dinaphtho[1,8‐ bc :1′,8′‐ fg ][1,5]dithiocine Bisimide
Author(s) -
Tanaka Yuki,
Tajima Keita,
Fukui Norihito,
Shinokubo Hiroshi
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000722
Subject(s) - chemistry , perylene , heteroatom , sulfur , dihedral angle , derivative (finance) , crystallography , computational chemistry , molecule , organic chemistry , ring (chemistry) , hydrogen bond , financial economics , economics
V‐shaped π‐systems are attractive research targets in organic chemistry and materials science. Our group has recently demonstrated that the conceptual insertion of a heteroatom into a perylene bisimide (PBI) core is an effective guideline for the design of non‐planar PBI derivatives. Here we report the synthesis and properties of dinaphtho[1,8‐ bc :1′,8′‐ fg ][1,5]dithiocine bisimide (DNDTBI), which represents a doubly sulfur‐inserted PBI derivative. The X‐ray diffraction analysis revealed that DNDTBI adopted a V‐shaped structure with a dihedral angle of 67°. DNDTBI exhibited higher electron‐donating ability than singly sulfur‐inserted PBI derivative owing to the antibonding interaction between the two neighboring sulfur atoms. The inversion barrier of the flipping motion of DNDTBI was ca. 30 kcal mol −1 , indicating the rigid nature of the V‐shaped structure.