50670-58-1Relevant articles and documents
Structure-property relationships in multi-stimuli responsive BODIPY-biphenyl-benzodithiophene TICT rigidochromic rotors exhibiting (pseudo-)Stokes shifts up to 221 nm
Sharma, Sushil,Wei, Zimu,Grozema, Ferdinand C.,Sengupta, Sanchita
, p. 25514 - 25521 (2020)
Structure-property relationships of donor-π-acceptor (D-π-A) type molecular dyad (pp-AD) and triads (pp-ADA and Me-pp-ADA) based on benzodithiophene and BODIPY with biphenyl spacers have been reported. Rotors pp-AD and pp-ADA showed efficient twisted intramolecular charge transfer (TICT) with near infrared (NIR) emissions at ～712 nm and ～725 nm with (pseudo-)Stokes shifts of ～208 nm and ～221 nm, respectively, and prominent solvatochromism. A structurally similar triad, Me-pp-ADA, with tetramethyl substituents on the BODIPY core instead was TICT inactive and exhibited excitation energy transfer with a transfer efficiency of ～88% as revealed using steady state emission and transient absorption measurements. Rotors pp-AD and pp-ADA showed NIR emission with an enhancement in intensity with the addition of water in THF solution as well as a pronounced change in emission intensity with temperature and viscosity variations, which justify their utility as temperature and viscosity sensors. Furthermore, the linear correlation of lifetime with fluorescence intensity ratios of the donor and acceptor justifies the rigidochromic behaviour of these rotors. This journal is
Quaterphenylterpyridine: Synthesis and metal-ion complexation
Lee, Young Hoon,Fuyuhiro, Akira,Harrowfield, Jack M.,Kim, Yang,Sobolev, Alexandre N.,Hayami, Shinya
, p. 5862 - 5870 (2013)
A quaterphenylterpyridine ligand (qptpy) with the rodlike quaterphenyl unit attached in the 4′-position has been synthesised by a Pd-catalysed Suzuki cross-coupling reaction. A crystal structure determination on the complex [Zn(qptpy)Cl2]·dmf (
Highly twisted bipolar emitter for efficient nondoped deep-blue electroluminescence
Huang, Zhi,Wang, Bo,Zhang, Qing,Xiang, Songpo,Lv, Xialei,Ma, Lixiang,Yang, Bing,Gao, Yu,Wang, Lei
, p. 328 - 336 (2017)
Three novel bipolar deep-blue emitters, 1-(4-(tert-butyl)phenyl)-2-(4-(9,9-diphenylacridin-10(9H)-yl)phenyl)-1H-phenanthro[9,10-d]imidazole (DPACTPI), 1-(4-(tert-butyl)phenyl)-2-(4'-(9,9-diphenylacridin-10(9H)-yl)-[1,1'-biphenyl]-4-yl)-1H-phenanthro[9,10-d]imidazole (DPACPhTPI) and 2-(4-(9,9-diphenylacridin-10(9H)-yl)phenyl)-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazole (DPACFPPI), employing the donor 9,9-diphenyl-9,10-dihydroacridine (DPAC) and the acceptor, phenanthroimidazole, were designed and synthesized. The highly twisted conformations between DAPC and phenanthroimidazole in the molecules efficiently interrupt molecular π-conjugation and inhibit π-π intermolecular interactions, resulting in good thermal stability and efficient deep-blue emission. The three phenanthroimidazole derivatives in non-doped OLEDs exhibited deep-blue emission. In particular, DPACPhTPI-based nondoped device showed an excellent performance with maximum external quantum efficiency (EQE) of 3.50%, maximum current efficiency (CE) of 1.38 cd/A, maximum power efficiency (PE) of 1.40 lm/W and CIE coordinate of (0.156, 0.047), which is among the best results for OLEDs with a similar color. The high radiative exciton utilization could be resulted from hybridized local and charge transfer (HLCT).
Functionalised phosphonate ester supported lanthanide (Ln = La, Nd, Dy, Er) complexes
Koehne, Ingo,Lik, Artur,Gerstel, Miriam,Bruhn, Clemens,Reithmaier, Johann Peter,Benyoucef, Mohamed,Pietschnig, Rudolf
supporting information, p. 16683 - 16692 (2020/12/18)
A series of phosphonate ester supported lanthanide complexes bearing functionalities for subsequent immobilisation on semiconductor surfaces are prepared. Six phosphonate ester ligands (L1-L6) with varying aromatic residues are synthesised. Subsequent com
Synthesis, characterization and catalytic performance of palladium supported on pyridine-based covalent organic polymer for Suzuki-Miyaura reaction
Han, Yi,Di, Jia-Qi,Zhao, Ai-Dong,Zhang, Zhan-Hui
, (2019/08/22)
A bipyridine-based covalent organic polymer (COP) was successfully synthesized by condensation of trimesoyl chloride (TMC) and 2,2′-bipyridine-5,5′-diamine (Bpy) under ambient conditions. This material was modified by coordination of PdCl2 to COP framework, affording a hybrid material, Pd@TMC-Bpy COP, which was applied as a highly efficient heterogeneous catalyst for Suzuki-Miyaura reaction under ligand-free conditions in ethyl lactate. The catalyst could be reused for five times without obvious loss of its activity.
Aminal-Linked Covalent Organic Frameworks through Condensation of Secondary Amine with Aldehyde
Jiang, Shu-Yan,Gan, Shi-Xian,Zhang, Xi,Li, Hui,Qi, Qiao-Yan,Cui, Fu-Zhi,Lu, Jian,Zhao, Xin
supporting information, p. 14981 - 14986 (2019/10/22)
New linkage chemistry will endow covalent organic frameworks (COFs) with not only structural diversity but also fascinating properties. However, to develop a new type of linkages has been a great challenge. We herein report the first two COFs using aminal
Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Dughera, Stefano
, p. 5758 - 5769 (2018/09/10)
Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.
VP1 crystal structure-guided exploration and optimization of 4,5-dimethoxybenzene-based inhibitors of rhinovirus 14 infection
Da Costa, Laurène,Roche, Manon,Scheers, Els,Coluccia, Antonio,Neyts, Johan,Terme, Thierry,Leyssen, Pieter,Silvestri, Romano,Vanelle, Patrice
, p. 453 - 462 (2016/04/19)
Human rhinoviruses (HRV) are the predominant cause of common colds and flu-like illnesses, but are also responsible for virus-induced exacerbations of asthma and chronic obstructive pulmonary disease. However, to date, no drug has been approved yet for clinical use. In this study, we present the results of the structure-based lead optimization of a class of new small-molecule inhibitors that we previously reported to bind into the pocket beneath the canyon of the VP1 protein. A small series of analogues that we designed based on the available structure and interaction data were synthesized and evaluated for their potency to inhibit the replication of HRV serotype 14. 2-(4,5-Dimethoxy-2-nitrophenyl)-1-(4-(pyridin-4-yl)phenyl)ethanol (3v) was found to be a potent inhibitor exhibiting micromolar activity (EC50 Combining double low line 3.4 ± 1.0 μM) with a toxicity for HeLa cells that was significantly lower than that of our previous hit (LPCRW-0005, CC50 Combining double low line 104.0 ± 22.2 μM; 3v, CC50 > 263 μM).
Synthesis of a terphenyl substituted 4-aza-2,3-didehydropodophyllotoxin analogues as inhibitors of tubulin polymerization and apoptosis inducers
Kamal, Ahmed,Tamboli, Jaki R.,Lakshma Nayak,Adil,Vishnuvardhan,Ramakrishna
, p. 2714 - 2723 (2014/05/06)
A series of terphenyl based 4-aza-2,3-didehydropodophyllotoxin conjugates (8a-r) were synthesized by a straightforward one-step multicomponent synthesis that demonstrated anticancer activity against five human cancer cell lines (lung, colon, renal, prostate and cervical). All the tested compounds showed potent anticancer activity with IC50 values ranging from 0.87 to 16.59 μM. Among them compounds 8n and 8p showed significant anticancer activity in lung cancer cells with IC50 values 0.91 and 0.87 μM, respectively. Flow cytometric analysis revealed that these compounds induced cell cycle arrest in G2/M phase in A549 cell line leading to caspase-3 dependent apoptotic cell death. The tubulin polymerization assay and immunofluorescence analysis showed that these compounds effectively inhibit microtubule assembly at both molecular and cellular levels in A549 cells. Further, Hoechst staining, DNA fragmentation analysis also suggested that these compounds induced cell death by apoptosis. Overall, the current study demonstrated that the synthesis of terphenyl based 4-aza-2,3- didehydropodophyllotoxin conjugates as promising anticancer agents with G 2/M cell cycle arrest and apoptotic-inducing activities via targeting tubulin.
Electron transfer and binding affinities in an electrochemically controlled ligand transfer system containing zinc porphyrin and a meso-phenylenediamine substituent
Cheng, Hsu Chun,Chen, Peter Ping Yu,Su, Yuhlong Oliver
, p. 1424 - 1433 (2014/01/06)
Investigations on the transfer of the ligand, imidazole (HIm), between two covalently linked redox centres-zinc porphyrin and phenylenediamine (PD)-and the influence of the length of the linker are reported. Since the binding affinity of the ligand with zinc porphyrin is different from that of the ligand with the phenylenediamine moiety, the transfer of the ligand could be electrochemically controlled by adjusting the oxidation potentials. Changes in cyclic voltammograms and absorption spectra of the complexes revealed the site of ligand binding in the various oxidation states of the modified zinc porphyrins. Binding constants of the modified zinc porphyrins in various oxidation states were also determined by photometric titration with the ligand and digital simulations. Evidence for the delocalization of the electron from the zinc porphyrin to the phenylenediamine moiety and the influence of the delocalization on them were obtained from EPR studies. The Royal Society of Chemistry 2014.
