18246-28-1Relevant articles and documents
Macrocyclic Oligothiophene with Stereogenic [2.2]Paracyclophane Scaffolds: Chiroptical Properties from π-Transannular Interactions
Hasegawa, Masashi,Kobayakawa, Kosuke,Matsuzawa, Hideyo,Nishinaga, Tohru,Hirose, Takashi,Sako, Katsuya,Mazaki, Yasuhiro
, p. 3267 - 3271 (2017)
The enantiomers of a new cyclic oligothiophene, bridged by two pseudo-ortho[2.2]paracyclophanes, were synthesized as a new class of the chiral π-conjugated system. Single-crystal X-ray diffraction analysis revealed a twisted structure for these oligothiophenes induced by a torsion of the cyclophane moieties. The embedding oligothiophenes into the inherent planar chirality provided a significant enhancement in circular dichroism (CD) spectra thanks to the large magnetic/electric transition dipole moments. In the dicationic state, an intramolecular π dimer was formed due to the strong interactions of the oligothiophenes. We further recorded unprecedented wide ranges of CD spectra in 250–1800 nm region. The transitions are reasonably described by the exciton coupling of the oligothiophenes.
Deprotonative C-H silylation of functionalized arenes and heteroarenes using trifluoromethyltrialkylsilane with fluoride
Sasaki, Midori,Kondo, Yoshinori
, p. 848 - 851 (2015)
A highly selective C-H silylation reaction of functionalized arenes and heteroarenes was developed using Ruppert-Prakash reagent (TMSCF3) activated by alkali metal fluoride. TMSCF3 is considered to play dual roles as a precursor of a mild base and also as a silicon electrophile. The silylation is compatible with sensitive functional groups such as halogen and nitro groups.
COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (HETEROARYLENE SPACER MOIETY)
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Page/Page column 40; 41, (2013/03/26)
The inventions disclosed and described herein relate to new and efficient generic methods for making a wide variety of compounds having HAr - Z - Har tricyclic cores, wherein HAr is an optionally substituted five or six membered heteroaryl ring, and Hal is a halogen, and Z is a bridging radical, such as S, Sc, NR5, C(O), C(O)C(O), Si(R5)2, SO, S02, PR5, BR5, C(R5)2 or P(O)Rs and both HAr are covalently bound to one another. The synthetic methods employ a "Base-Catalyzed Halogen Dance" reaction to prepare a metallated compound comprising a five or six membered heteroaryl ring comprising a halogen atom, and then oxidatively coupling the reactive intermediate compound. The compounds of Formula (II) and/or oligomer or polymers comprising repeat units having Formula (II) can be useful for making semi-conducting materials, and/or electronic devices comprising those materials. Acyl compounds can be prepared. Heteroarylene substituents can be used. The core tricyclic core can be coupled to itself. The Z group also can be strong electron-withdrawing groups such as C=C(CN)2 or [C=C(CN)212. Organic electronic devices can be made including field-effect transistors. Formula (II).