Systematic Synthesis
of Tetrathia[8]circulenes: The
Influence of Peripheral Substituents on the Structures and Properties
in Solution and Solid States
Posted on 2019-08-25 - 12:31
We developed the
diversity-oriented approach for the synthesis
of tetrathia[8]circulenes with a variety of peripheral substituents.
Iridium-catalyzed direct C–H borylation of tetrathienylene
provided 1,4,7,10-tetraboryltetrathienylene as a major product.
1,4,7,10-Tetraboryltetrathienylene served as an a key
intermediate to achieve the selective synthesis of octasubstituted
or tetrasubstituted tetrathia[8]circulenes via rhodium-catalyzed
annulation with symmetric internal alkynes or sequential Sonogashira–Hagihara
coupling and base-promoted intramolecular cyclization. A variety of
substituents were installed at the peripheral positions of tetrathia[8]circulenes
systematically. The self-assembling behavior of tetrathia[8]circulenes
was investigated using 1H NMR and AFM measurements. The
number and the chain length of alkyl groups exerted a significant
influence on the aggregation ability and the crystal packing structures
of tetrathia[8]circulenes in both solution and solid states. We also
found that the molecular arrangement of the self-assembled tetrathia[8]circulene
molecules affected the hole mobility assessed by the FP-TRMC method.
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Kato, Shohei; Akahori, Shuhei; Serizawa, Yuma; Lin, Xu; Yamauchi, Mitsuaki; Yagai, Shiki; et al. (2019). Systematic Synthesis
of Tetrathia[8]circulenes: The
Influence of Peripheral Substituents on the Structures and Properties
in Solution and Solid States. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.9b01655
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AUTHORS (11)
SK
Shohei Kato
SA
Shuhei Akahori
YS
Yuma Serizawa
XL
Xu Lin
MY
Mitsuaki Yamauchi
SY
Shiki Yagai
TS
Tsuneaki Sakurai
WM
Wakana Matsuda
SS
Shu Seki
HS
Hiroshi Shinokubo
YM
Yoshihiro Miyake