18937-92-3Relevant articles and documents
Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way
Zhao, Long,Prendergast, Matthew B.,Kaiser, Ralf I.,Xu, Bo,Ablikim, Utuq,Ahmed, Musahid,Sun, Bing-Jian,Chen, Yue-Lin,Chang, Agnes H. H.,Mohamed, Rana K.,Fischer, Felix R.
, p. 17442 - 17450 (2019)
Polycyclic aromatic hydrocarbons (PAHs) represent the link between resonance-stabilized free radicals and carbonaceous nanoparticles generated in incomplete combustion processes and in circumstellar envelopes of carbon rich asymptotic giant branch (AGB) stars. Although these PAHs resemble building blocks of complex carbonaceous nanostructures, their fundamental formation mechanisms have remained elusive. By exploring these reaction mechanisms of the phenyl radical with biphenyl/naphthalene theoretically and experimentally, we provide compelling evidence on a novel phenyl-addition/dehydrocyclization (PAC) pathway leading to prototype PAHs: triphenylene and fluoranthene. PAC operates efficiently at high temperatures leading through rapid molecular mass growth processes to complex aromatic structures, which are difficult to synthesize by traditional pathways such as hydrogen-abstraction/acetylene-addition. The elucidation of the fundamental reactions leading to PAHs is necessary to facilitate an understanding of the origin and evolution of the molecular universe and of carbon in our galaxy.
Rhodium-Catalyzed Synthesis of Chiral Monohydrosilanes by Intramolecular C?H Functionalization of Dihydrosilanes
Ma, Wenpeng,Liu, Li-Chuan,An, Kun,He, Tao,He, Wei
, p. 4245 - 4251 (2021)
The preparation of chiral monohydrosilanes remains a rarely achieved goal. To this end a Rh-catalyzed desymmetrization of dihydrosilanes by way of intramolecular C(sp2)?H functionalization under simple and mild conditions has now been developed
Monobenzofused 1,4-azaborines: Synthesis, characterization, and discovery of a unique coordination mode
Xu, Senmiao,Haeffner, Fredrik,Li, Bo,Zakharov, Lev N.,Liu, Shih-Yuan
, p. 6795 - 6799 (2014)
We report the first general synthesis of boron-substituted monobenzofused 1,4-azaborines using ring-closing metathesis of an enamine-containing diene as a key synthetic strategy. As part of our investigations, we discovered that the B-C3 moiety in a 1,4-a
A Guide for the Design of Functional Polyaromatic Organophosphorus Materials
Hindenberg, Philip,López-Andarias, Alicia,Rominger, Frank,de Cózar, Abel,Romero-Nieto, Carlos
, p. 13919 - 13928 (2017)
The impact of integrating six-membered phosphorus heterocycles into a poly(hetero)aromatic materials is investigated. Mechanistic studies reveal the key synthetic requirements to embed the latter phosphorus heterocycles in polyaromatic molecules. DFT calc
Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
, p. 9047 - 9052 (2021/12/06)
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
Dephosphinylative [4 + 2] Benzannulation of Phosphinyl Ynamines: Application to the Modular Synthesis of Polycyclic Aromatic Amines
Okuda, Yasuhiro,Fujimoto, Mayo,Akashi, Haruo,Orita, Akihiro
supporting information, p. 17651 - 17666 (2021/12/13)
A series of 9-amino-10-halophenanthrenes were synthesized through a one-pot process, including dephosphinylative Sonogashira–Hagihara coupling of 2-bromobiphenyls with air-stable phosphinyl ynamines, followed by halonium-promoted [4 + 2] benzannulation of the resulting 2-(aminoethynyl)biphenyls. Nonsubstituted and methyl-substituted 2-bromobiphenyls rapidly underwent the Sonogashira–Hagihara aminoethynylation and the halogenative Friedel–Crafts benzannulation to provide the corresponding amino(halo)phenanthrenes in high yields, while electron-sufficient and -deficient substrates did slowly undergo the former and the latter to result in low yields, respectively. This protocol worked well for the syntheses of highly π-extended aminophenanthrenes and aminobenzonaphthothiophenes with different optical properties. Further application of this approach between 2,2″- and 2′,5′-dibromo-p-terphenyls with phosphinyl ynamines led to the regioselective formation of 6,13-diamino-5,12-dihalo- and 5,12-diamino-6,13-dihalo-dibenz[a,h]anthracenes via dual aminoethynylation and [4 + 2] benzannulation. The obtained analogues showed different ultraviolet–visible absorption and photoluminescence spectra with different emission quantum yields in CH2Cl2 solution and the powder state.
Organic electroluminescent compound
-
Paragraph 0049-0053; 0069-0070, (2020/11/11)
The invention provides an organic electroluminescent compound. The organic electroluminescent compound has a structure as shown in a formula (I) or formula (II) which is described in the specification. In the formulas, R1 to R4 are selected from the group consisting of H, halogen, cyano groups, C1-C20 chain alkyl groups, C1-C20 halogenated chain alkyl groups, C3-C20 cycloalkyl groups, C3-C20 halogenated cycloalkyl groups, C1-C20 alkoxy groups, C1-C20 silicyl groups, aryloxy groups with a cyclization carbon number of 6 to 30, aryl groups with a cyclization carbon number of 6 to 30, and heterocyclic aryl groups with a cyclization carbon number of 6 to 30; and Ar1 and Ar2 are independently selected from the group consisting of aryl groups with a cyclization carbon number of 6 to 30, and heterocyclic aryl groups with a cyclization carbon number of 6 to 30. The organic electroluminescent compound of the invention has excellent electron blocking properties and a high glass transition temperature. An OLED device prepared from the organic electroluminescent compound of the invention shows lower operating voltage, higher current efficiency and longer service life; therefore, the OLED device has good application value and excellent market potential.
Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization
Seo, Tamae,Kubota, Koji,Ito, Hajime
supporting information, p. 9884 - 9889 (2020/05/19)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity of the crystalline monoarylated products relative to the liquid starting materials should be attributed predominantly to the low diffusion efficiency of the former in the reaction mixture, which results in a selective monoarylation. The present study sheds light on a novel approach using in situ phase transitions in solids to design selective organic transformations that are difficult to achieve via conventional solution-based synthesis.
HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME
-
Paragraph 0182-0184, (2020/05/14)
The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.
NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
-
Paragraph 0165-0168, (2020/05/29)
Organic electroluminescent devices with lowered driving voltages, and enhanced efficiencies and lifetimes are provided.
