The author of 《Fluorination of the tetraphenylethene core: synthesis, aggregation-induced emission, reversible mechanofluorochromism and thermofluorochromism of fluorinated tetraphenylethene derivatives》 were Zhang, Hao; Nie, Yong; Miao, Jinling; Zhang, Dengqing; Li, Yexin; Liu, Guangning; Sun, Guoxin; Jiang, Xuchuan. And the article was published in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2019. Synthetic Route of C6H6BFO2 The author mentioned the following in the article:
The Suzuki-Miyaura cross-coupling reactions of bromoalkenes R(X)C=C(R1)R2 (R = C6H5, Br; R1 = C6H5, 4-FC6H4; R2 = C6H5, 4-FC6H4; X = Br) with fluorophenylboronic acids R3C6H4B(OH)2 (R3 = 2-F, 3,4-(F)2, 2,4,6-(F)3, etc.) afforded 17 fluorinated tetraphenylethene (FTPE) compounds RC(R3)=C(R1)R2 that have only fluorine substituent(s) directly on the tetraphenylethene (TPE) core with different numbers and substitution positions of the fluorine atom(s). The X-ray structures of four FTPEs show that these FTPE derivatives have C-H…F and C-H…π hydrogen bonds in the crystal packing. DFT calculations indicate that both the HOMOs and LUMOs of the FTPEs essentially have lower energy levels than those of the parent TPE, and the energy gaps are highly dependent on the substitution pattern. These FTPEs exhibit aggregation-induced emission characteristics similar to most TPE derivatives but the aggregation process was found to be gradual and time-dependent. The emission wavelengths of both aggregates from tetrahydrofuran/H2O and solids, and the corresponding emission quantum yields of the solid samples vary with different substitution patterns. In addition, two examples of these FTPEs show reversible mechanofluorochromic and thermofluorochromic properties (the latter was only shown on silica gel), while the parent TPE does not exhibit mechanochromism under the same conditions. In addition to this study using (3-Fluorophenyl)boronic acid, there are many other studies that have used (3-Fluorophenyl)boronic acid(cas: 768-35-4Synthetic Route of C6H6BFO2) was used in this study.
(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Synthetic Route of C6H6BFO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics