7206-61-3Relevant articles and documents
Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles
Shoji, Taku,Yokoyama, Ryuji,Ito, Shunji,Watanabe, Masataka,Toyota, Kozo,Yasunami, Masafumi,Morita, Noboru
, p. 1099 - 1103 (2007)
Azulene reacts with highly electrophilic trifluoromethanesulfonates of N-containing heterocycles to give 1-dihydroheteroaryl and 1,3-bis(dihydroheteroaryl)azulene derivatives in a good yield. Treatment of the dihydroheteroarylazulene derivatives with KOH or tert-BuOK afforded 1-heteroaryl and 1,3-bis(heteroaryl)azulenes in a good yield.
Adj-diazuliporphyrins, a new family of dicarbaporphyrinoids with unprecedented mesoionic characteristics
Zhang, Zhenjun,Ferrence, Gregory M.,Lash, Timothy D.
, p. 101 - 104 (2009)
A diazulenylmethane dialdehyde reacted with dipyrrylmethanes in the presence of HCl or HBr, followed by oxidation with FeCl3, to give aromatic adj-diazuliporphyrins. The free base structures must exist as mesoionic species, although these porphyrinoids were isolated as salts of the monoprotonated macrocycles. Reaction with Pd(OAc)2 gave an unprecedented zwitterionic palladium(II) complex that was characterized by X-ray crystallography.
Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)-Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides
Lee, Seung Cheol,Son, Jeong-Yu,Kim, Jin Young,Eom, Hyeonsik,Jang, Seong Bin,Lee, Phil Ho
, p. 512 - 524 (2020/11/30)
A regioselective and chemodivergent synthetic approach for azulenolactones and azulenolactams as a new scaffold was demonstrated through Rh(III)-catalyzed reaction of N-methoxyazulene-1-carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act as a precursor of secondary carbene was described, leading to the selective formation of azulenolactones and azulenolactams bearing two substituents on a newly introduced double bond. This method demonstrated functionalization of less reactive 2-position of azulene to overcome the natural reactivity. (Figure presented.).
Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C-H Activation: Rhodium- And Iridium-Catalyzed Oxidative Cyclization of Azulene Carboxylic Acids with Alkynes for the Synthesis of Azulenolactones and Benzoazulenes
Maeng, Chanyoung,Son, Jeong-Yu,Lee, Seung Cheol,Baek, Yonghyeon,Um, Kyusik,Han, Sang Hoon,Ko, Gi Hoon,Han, Gi Uk,Lee, Kyungsup,Lee, Kooyeon,Lee, Phil Ho
supporting information, p. 3824 - 3837 (2020/02/28)
Rhodium-catalyzed oxidative [4 + 2] cyclization reactions through the C-H activation of azulene carboxylic acids as nonbenzenoid aromatic compounds with symmetrical and unsymmetrical alkynes were developed under aerobic conditions, which produced azulenolactone derivatives with a wide substrate scope and excellent functional group tolerance. Interestingly, azulenic acids in reaction with alkynes underwent iridium-catalyzed [2 + 2 + 2] cyclization accompanied by decarboxylation to afford tetra(aryl)-substituted benzoazulene derivatives. The reactivity order for C-H activation reaction is greater toward azulene-6-carboxylic acid, azulene-1-carboxylic acid, and azulene-2-carboxylic acid. For the first time, the expansion of azulenes having directing group as nonbenzenoid aromatic compounds for C-H activation was successful, indicating that nonbenzenoid aromatic compounds can be used as good substrates for the C-H activation reaction. Therefore, the research area of C-H activation will certainly expand to nonbenzenoid aromatic compounds in future.
Gold-Catalyzed Direct Alkynylation of Azulenes
Székely, Anna,Péter, áron,Aradi, Klára,Tolnai, Gergely L.,Novák, Zoltán
, p. 954 - 957 (2017/02/26)
A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives were synthesized bearing important functional groups for further functionalization.
Selective Dual-Channel Imaging on Cyanostyryl-Modified Azulene Systems with Unimolecularly Tunable Visible–Near Infrared Luminescence
Zhou, Yunyun,Zhuang, Yaping,Li, Xin,?gren, Hans,Yu, Lin,Ding, Jiandong,Zhu, Liangliang
supporting information, p. 7642 - 7647 (2017/06/06)
Although organic light-emitting molecules have received a growing attention and applicability in modern bioimaging science, the design and control of complex photoluminescent properties in unimolecularly selective imaging remains a challenging topic. Cons
Nitrile-group-containing azulene-styrene derivatives adopted as near infrared fluorescence probe as well as preparation method and application of nitrile-group-containing azulene-styrene derivative
-
Paragraph 0025, (2017/01/23)
The invention belongs to the technical field of fluorochrome and particularly relates to nitrile-group-containing azulene-styrene derivatives as well as a preparation method and an application of the nitrile-group-containing azulene-styrene derivatives. T
Preparation of azulene-derived fulvenedialdehydes and their application to the synthesis of stable adj -dicarbaporphyrinoids
Lash, Timothy D.,Lammer, Aaron D.,Idate, Aparna S.,Colby, Denise A.,White, Kristen
experimental part, p. 2368 - 2381 (2012/05/05)
A "2 + 2" strategy for synthesizing adj-dicarbaporphyrinoid systems has been developed. In a model study, an azulenylmethylpyrrole dialdehyde was condensed with a dipyrrylmethane in the presence of HCl, followed by oxidation with ferric chloride, to give
Photophysical, electrochemical, and photoelectrochemical properties of new azulene-based dye molecules
Zhang, Xue-Hua,Li, Chao,Wang, Wei-Bo,Cheng, Xue-Xin,Wang, Xue-Song,Zhang, Bao-Wen
, p. 642 - 649 (2007/10/03)
Four new azulene-based dye molecules, 3-(azulen-1-yl)-2-cyanoacrylic acid (Azu-1), 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid (Guai-1), 5-(azulen-1-yl)-2-cyanopenta-2,4-dienoic acid (Azu-2), and 5-(7-isopropyl-1,4- dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid (Guai-2), were synthesized and their photoelectrochemical properties were studied in dye-sensitized solar cells (DSSCs). All of them exhibit, in the visible region, a strong absorption band coming from the S0-S2 transition and a very weak band coming from the S0-S1 transition, and the transition assignments are supported by theoretical calculations using time-dependent density functional theory (TD-DFT) at the B3LYP/6-31G* level. In sensitization of nanocrystalline TiO2 electrodes, reducing their adsorption amount on the TiO2 surface (by co-adsorption with deoxycholic acid) mitigates dye aggregation and improves their photoelectric conversion efficiency greatly. Also, extending the conjugated side chain (Azu-2 vs. Azu-1 or Guai-2 vs. Guai-1) not only shifts their photoelectric response to longer wavelengths and therefore enhances the short-circuit photocurrent, but also increases the open-circuit photovoltage significantly. Moreover, it was found that the electron injection efficiencies varied remarkably with excitation wavelength, suggesting direct electron injection from the S2 state of these dye molecules. The Royal Society of Chemistry.
Synthesis and reactions of N-(azulen-1-ylmethylene)arylamines
Razus,Nitu,Carvaci,Birzan,Razus,Pop,Tarko
, p. 1227 - 1233 (2007/10/03)
N-(Azulen-1-ylmethylene)arylamines, 5, were obtained in a fast quantitative conversion and high yield from the condensation of the corresponding azulene-1-carbaldehydes with aromatic amines without solvent. The reactions of the Schiff bases obtained, 5, w
