101327-84-8Relevant articles and documents
Introduction of benzo[h]quinoline and 1,10-phenanthroline subunits by friedl?nder methodology
Riesgo, Elvira C.,Jin, Xiaoqing,Thummel, Randolph P.
, p. 3017 - 3022 (1996)
An improved preparation of 8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedl?nder condensation of the quinoline derivative with a series of acetylaromatics provides the corresponding 2-aryl-1,10-phenanthrolines. Condensation of either amino aldehyde with 1,3-diacetylbenzene or 2,6-diacetylpyridine provides the expected Friedl?nder product. Similar chemistry is described for reactions of the amino aldehydes with 1,4-diacetylbenzene, 4,4′-diacetylbiphenyl, 1,5-diacetylanthracene, 1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione, and tetracyclo-[6.3.0.0.4,1105,9]undecane-2,7-dione (TCU-2,7-dione).
BN-Phenanthrenes: Synthesis, Reactivity, and Optical Properties
Zhang, Chen,Zhang, Lei,Sun, Chao,Sun, Wenfang,Liu, Xuguang
, p. 3476 - 3480 (2019)
Two series of BN-phenanthrenes, including the parental compounds, have been synthesized in an efficient manner from commercially available materials. Both parental BN-phenanthrenes are strongly fluorescent in solution. Their absorption and emission spectr
Novel functionalized indigo derivatives for organic electronics
Klimovich, Irina V.,Zhilenkov, Alexander V.,Кuznetsova, Lidiya I.,Frolova, Lubov A.,Yamilova, Olga R.,Troyanov, Sergey I.,Lyssenko, Konstantin A.,Troshin, Pavel A.
, (2020/11/24)
A series of nine novel indigo derivatives, including diiodoindigo, octahalogenated indigoids and compounds with extended π-conjugated system, were synthesized, characterized and investigated as semiconductor materials in organic field-effect transistors (OFETs). Among them, 6,6′-diiodoindigo demonstrated the ambipolar behavior with balanced p-type and n-type mobilities. The complete substitution of hydrogens at the indigo core with halogen atoms led to low electron mobilities in OFETs. An extension of the conjugated system through the introduction of small aromatic substituents (thiophene and phenyl) resulted in predominant p-type behavior. Fusion of aromatic rings resulted in z-shaped dibenzoindigo, which showed poor charge transport properties due to the non-optimal arrangement of molecules along each other in the crystal lattice. The acquired data fulfilled the previously reported model based on the relationship between the chemical nature of substituents and their positions at the indigo core, optoelectronic properties of materials and their performance in OFETs. The results of this study will be useful for rational design of a new generation of the indigo-based semiconductors for biocompatible organic electronics.
A facile synthesis of 2-methylquinolines via Pd-catalyzed aza-Wacker oxidative cyclization
Zhang, Zuhui,Tan, Jiajing,Wang, Zhiyong
, p. 173 - 175 (2008/09/18)
(Chemical Equation Presented) A novel Pd-catalyzed Wacker-type oxidative cyclization under air is described. By using this cyclization, a series of 2-methylquinolines are readily prepared with good yields under mild conditions.
