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Synthesis, Photophysical Properties, and Self‐Organization of Difurobenzosilole Derivatives
Author(s) -
Li Liangchun,
Li Shuhong,
Zhao CuiHua,
Xu Caihong
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201400061
Subject(s) - dibenzofuran , chemistry , toluene , thermal stability , electrophile , silicon , furan , electron deficiency , suzuki reaction , photochemistry , combinatorial chemistry , organic chemistry , catalysis , palladium
A facile synthetic route was developed to fuse furan rings to a dibenzosilole core for the construction of difurobenzosilole derivatives through an electrophilic double cyclization reaction. Only silafluorene derivatives with electron‐donating groups on the periphery participated in this cyclization. Suzuki–Miyaura coupling and deiodination of the diiododifurobenzosiloles resulted in highly emissive silicon‐bridged dibenzofuran compounds. These obtained compounds exhibited very high luminescent quantum yields (93 to about 99 %) and good thermal stability. Single crystals of the silicon‐bridged dibenzofuran compound with a marginal phenyl group were easily grown and analyzed by single‐crystal X‐ray diffraction, whereas the deiodinated silicon‐bridged dibenzofuran compound showed a high tendency to self‐organize into 1D microfibers in various solvents such as hexane, toluene, and THF.