42196-97-4Relevant academic research and scientific papers
9-vinylanthracene based fluorogens: Synthesis, structure-property relationships and applications
Liu, Mengjie,Onchaiya, Sawaros,Tan, Lewis Yi Fong,Haghighatbin, Mohammad A.,Luu, Tracey,Owyong, Tze Cin,Hushiarian, Roozbeh,Hogan, Conor F.,Smith, Trevor A.,Hong, Yuning
, (2017)
Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using fluorometric analyses, these dyes were confirmed to show AIE behavior upon forming aggregates at high concentrations, in viscous solvents, and when poorly solubilized. Their photophysical properties were then further correlated with their structural features, using density functional theory (DFT) calculation. Finally, we demonstrated their potential applications in monitoring pH changes, quantifying globular proteins, as well as cell imaging with confocal microscopy.
On the Relationship between Molecular Geometry and Excited-State Properties of 9-Anthrylalkenes
Becker, Hans-Dieter,Andersson, Kjell
, p. 4542 - 4549 (1983)
The excited-state properties of a series of 1-substituted and 1,1-disubstituted 2-(9-anthryl)alkenes have been investigated in terms of their fluorescence spectra and photochemical isomerizations.Large Stokes shifts of up to 10000 cm-1 between absorption and emission maxima are attributed to geometrical differences between the ground state and the emitting excited state.The : ratio of the photostationary state was found to depend markedly on the nature of the 1-substituent.Photochemical isomerization of 1,3- and 1,5-bis(9-anthryl)-substituted trans olefins results in the formation of intramolecular or cycloaddition products.The cycloaddition reactions of carbonyl-substituted anthracenes are suggested to involve the triplet excited state.
N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions
Li, Dan,Tian, Qingqiang,Wang, Xuetong,Wang, Qiang,Wang, Yin,Liao, Siwei,Xu, Ping,Huang, Xin,Yuan, Jianyong
supporting information, p. 2041 - 2052 (2021/05/25)
A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.
Two trans-1-(9-anthryl)-2-phenylethene derivatives as blue-green emitting materials for highly bright organic light-emitting diodes application
Zhou, Nonglin,Shao, Xiaona,Wang, Shirong,Xiao, Yin,Li, Xianggao
, p. 228 - 238 (2017/08/08)
1-(9-Anthryl)-2-phenylethene (t-APE) is a blue-green material with high fluorescence quantum yield (Фf 0.44). However, it is easily crystallized. Herein, Two asymmetric blue-green emitting materials based on t-APE, (E)-9-(4-(2-(anthracen-9-yl)vinyl)phenyl)-10-(naphthalen-1-yl)anthracene (6) and (E)-9-(4-(2-(anthracen-9-yl)vinyl)phenyl)-10-(naphthalen-2-yl)anthracene (7) were firstly designed and synthesized. The two compounds possess high thermal stability, morphological durability, and bipolar characteristics. The non-doped blue-green organic light-emitting diodes (OLEDs) using 6 and 7 as emitting layers showed emission at 495 nm, full width at half maximum of 80 nm, maximum brightness of 13,814, 10,579 cd m?2, maximum current efficiency of 3.62, 7.16 cd A?1, and Commission Internationale de L'Eclairage (CIE) coordinate of (0.20, 0.43), respectively. Furthermore, when employing 6 and 7 as blue-green emitting layers and rubrene doped in tris-(8-hydroxyquinolinato)aluminum (Alq3) as the orange emitting layers to fabricate white OLEDs (WOLEDs), the WOLEDs exhibit a maximum brightness of 10,984, 14,652 cd m?2, maximum current efficiency of 2.04, 2.70 cd A?1, and CIE coordinate of (0.30, 0.40), (0.37, 0.47), Color Rendering Index (CRI) of 65, 60, stable EL spectra, respectively. This study demonstrates that the t-APE-type derivatives have the excellent properties for the emitting materials of OLEDs.
Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives
Ismail, Tabasum,Shafi, Syed,Srinivas, Jada,Sarkar, Dhiman,Qurishi, Yasrib,Khazir, Jabeena,Alam, Mohammad Sarwar,Kumar, Halmuthur Mahabalarao Sampath
, p. 97 - 102 (2016/01/25)
Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.
Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents
Link, Achim,Fischer, Christian,Sparr, Christof
supporting information, p. 12163 - 12166 (2015/10/12)
A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.
Synthesis and photochemical transformations of a few olefin-appended 11,12-dibenzoyldibenzobarrelenes
Jacob, Ambily Mary,George, Gisha,Jacob, Jomon P.,Mathew, Eason M.
, p. 199 - 202 (2015/06/02)
Several olefin-appended dibenzobarrelenes have been synthesised by Diels-Alder reaction between 9-alkenylanthracenes and dibenzoylacetylene under carefully controlled conditions and their photochemistry was examined. Olefin appendages acted as efficient quenchers of the triplet state of these barrelenes.
Synthesis and characterization of para-pyridine linked NHC palladium complexes and their studies for the Heck-Mizoroki coupling reaction
Liu, Ya-Ming,Lin, Yi-Chun,Chen, Wen-Ching,Cheng, Jen-Hao,Chen, Yi-Lin,Yap, Glenn P. A.,Sun, Shih-Sheng,Ong, Tiow-Gan
experimental part, p. 7382 - 7389 (2012/07/31)
This paper describes the synthesis of 1-(pyridine-4-ylmethyl) NHC and their Pd(ii) and Ag(i) complexes, which are fully characterized. Interestingly, we have also synthesized a Pd complex 3a-CO3 using a more direct treatment of K2CO3 with PdCl2. 3a-CO 3 represents the first reported solid structure of a Pd η2-carbonato complex stabilized by an NHC framework. 3a-CO 3 can be easily converted to a PdCl2 derivative by treating it with chloroform. We have found these palladium complexes mediate the Heck-Mizoroki coupling with a low catalyst loading. Furthermore, we also expand such catalytic manifold toward constructing fused polyaromatic substrates, a highly useful class of compounds in optoelectronic chemistry.
Highly chemo- and stereoselective palladium-catalyzed transfer semihydrogenation of internal alkynes affording cis -alkenes
Li, Jie,Hua, Ruimao,Liu, Tao
supporting information; experimental part, p. 2966 - 2970 (2010/06/19)
DMF (N,N-dimethylformamide)/KOH was found to be an efficient hydrogen source in the Pd(OAc)2-catalyzed transfer semihydrogenation of various functionalized internal alkynes to afford cis-alkenes in good to high yields with excellent chemo- and stereoselectivity. This catalytic process was also applied to the synthesis of analogues of combretastatin A-4.
A new efficient tetraphosphine/palladium catalyst for the Heck reaction of aryl halides with styrene or vinylether derivatives
Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
, p. 2191 - 2194 (2007/10/03)
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system efficiently catalyses the Heck reaction of aryl halides with styrene and vinylether derivatives. High turnover numbers can be obtained for the reaction of several aryl halides with styrene and styrene derivatives. Lower turnover numbers have been observed in the presence of vinylethers.
