10135-00-9Relevant articles and documents
Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine
Shigeno, Masanori,Fujii, Yuki,Kajima, Akihisa,Nozawa-Kumada, Kanako,Kondo, Yoshinori
, p. 443 - 451 (2019)
Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.
Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
Fredrich, Sebastian,Bonasera, Aurelio,Valderrey, Virginia,Hecht, Stefan
, p. 6432 - 6440 (2018)
Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.
Naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene-based semiconductors for organic field-effect transistors
Li, Zhaoguang,Zhang, Ji,Zhang, Kai,Zhang, Weifeng,Guo, Lei,Huang, Jianyao,Yu, Gui,Wong, Man Shing
supporting information, p. 8024 - 8029 (2015/08/06)
A novel series of air-stable and highly extended π-conjugated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene derivatives, NBTBT-n (n = 6, 8, 10, and 12) and NBTBTF-10, was developed. The influence of various alkoxy-side groups including straight chain with different chain lengths and branched chain on the FET device performance was also investigated. There was a progressive enhancement in the NBTBT-based OFET device performance with an increase in the annealing temperature. The OFET devices based on NBTBT-10 fabricated by vacuum deposition exhibited the best performance with a hole mobility of 0.25 cm2 V-1 s-1 and an on/off ratio of 105-106 after annealing at 220 °C. In addition, fluorinated naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene, NBTBTF-10, showed good p-type transistor behaviour with a hole mobility of 0.24 cm2 V-1 s-1 and an on/off ratio of 106-107 which was achieved at a lower annealing temperature of 140 °C, suggesting the important contribution of the dipole-dipole interactions induced by the fluorine atoms in the molecular packing. As a result, the naphtho[2,1-b:3,4-b′]bisthieno[3,2-b][1]benzothiophene framework shows promise as a useful building block to construct organic semiconductors for next-generation high performance organic electronics.