81344-89-0Relevant academic research and scientific papers
Photomechanical Luminescence from Through-Space Conjugated AIEgens
Fan, Jianzhong,Guo, Jingjing,Liu, Xinzhi,Tang, Ben Zhong,Zhao, Zujin
supporting information, p. 8828 - 8832 (2020/03/04)
Transforming molecular motions into the macroscopic scale is a topic of great interest to nanoscience. The photomechanical effect is a promising strategy to achieve this goal. Herein, we report an intriguing photomechanical luminescence driven by the photodimerization of 2-phenylbenzo[b]thiophene 1,1-dioxide (P-BTO) in molecular crystals and elucidate the working mechanism and substituent effect through crystallographic analysis and theoretical calculations. Striking splitting, hopping, and bending mechanical behaviors accompanied by a significant blue fluorescence enhancement are observed for P-BTO crystals under UV light, which is attributed to the formation of photodimer 2P-BTO. Although 2P-BTO is poorly π-conjugated because of the central cyclobutane ring, it exhibits prominent through-space conjugation and aggregation-induced emission (AIE), affording strong solid-state blue fluorescence at 415 nm with an excellent quantum yield of up to 96.2 %.
Iridium-Catalyzed Asymmetric Hydrogenation of Benzo[b]thiophene 1,1-Dioxides
Tosatti, Paolo,Pfaltz, Andreas
supporting information, p. 4579 - 4582 (2017/04/11)
An efficient iridium-catalyzed asymmetric hydrogenation of substituted benzothiophene 1,1-dioxides is described. The use of iridium complexes with chiral pyridyl phosphinite ligands provides access to highly enantiomerically enriched sulfones with substituents at the 2- and 3-position. Sulfones of this type are of interest as core structures of agrochemicals and pharmaceuticals. Moreover, they can be further reduced to chiral 2,3-dihydrobenzothiophenes.
Addition Reactions of Benzothiophen. Part 3. Addition and Ring-opening Reactions with Phenolic Ethers
Clark, Peter David,Ewing, David F.,Kerrigan, Frank,Scrowston, Richard M.
, p. 615 - 622 (2007/10/02)
In the presence of aluminium chloride, anisole, phenetole, diphenyl ether, and (methylthio)benzene are added rapidly across the 2,3-bond in benzothiophen to give, inter alia, a mixture of 2- and 3-(p-substituted aryl)-2,3-dihydrobenzothiophens (3) and (4).Contrary to expectation, the 2-isomer predominates in all cases, and the addition is irreversible.Reaction with anisole also leads to a novel ring-opened product, viz. (E)-4-methoxy-2'-methylthiostilbene (9a), which was synthesised unambigiuously.It is believed that benzothiophen is S-methylated by PhOMe-AlCl3 in a 'push-pull' reaction, and that the resulting positive charge is delocalised into the ring, thus allowing the 2-position to participate in electrophilic attack on a second molecule of anisole.The resulting quadrivalent sulphur intermediate achieves stabilisation by means of a rapid ring-opening reaction.Other aromatic methyl ethers give analogous products, but phenetole diphenyl ether, and (methylthio)benzene do not promote ring-opening.The ring-opening reaction is aided by the addition of MeBr- or EtBr-AlCl3; even phenetole will then undergo ring-opening.Under these conditions the S-alkyl group in the ring-opened product comes from the starting ether, and not from the added MeBr or EtBr.
