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Accessing π‐expanded heterocyclics beyond dibenzothiophene: Syntheses and properties of phenanthrothiophenes
Author(s) -
Venkateswarlu Samala,
Prakoso Suhendro Purbo,
Kumar Sushil,
Tao YuTai
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201900509
Subject(s) - chemistry , regioselectivity , thiophene , dibenzothiophene , antiparallel (mathematics) , chloride , catalysis , crystallography , stereochemistry , combinatorial chemistry , organic chemistry , magnetic field , physics , quantum mechanics
A series of phenanthrothiophenes are designed and synthesized from polyarylthiophenes through regioselective Scholl reactions in one step using iron chloride as catalyst. The molecular structures of these heteroarenes displayed multiple twisted fjords, which perturb the shapes of the polycyclic frameworks to pack in slipped to near‐perfect face‐to‐face styles in parallel or antiparallel packings. Field‐effect transistor devices using single crystals of 6,12‐difluorodiphenanthro[9, 10‐b:9′, 10′]thiophene gave a hole mobility of 0.22 cm 2 V −1 s −1 .