2039-80-7Relevant articles and documents
Arcus,Hall
, p. 4199,4200 (1963)
Novel 1,8-naphthalimide derivatives for standard-red organic light-emitting device applications
Luo, Shuai,Lin, Jie,Zhou, Jie,Wang, Yi,Liu, Xingyuan,Huang, Yan,Lu, Zhiyun,Hu, Changwei
, p. 5259 - 5267 (2015)
Three red-emissive D-π-A-structured fluorophores with an aromatic amine as the donor, ethene-1,2-diyl as the π-bridge, and 1,8-naphthalimide as the acceptor subunit, namely, (E)-6-(4-(dimethylamino)styryl)-2-hexyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (Nap1), (E)-2-(2,6-di(isopropyl)phenyl)-6-(4-(dimethylamino)styryl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (Nap2) and (E)-2-(2,6-di(isopropyl)phenyl)-6-(2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (Nap3), were designed and synthesized. In-depth investigations on the correlations between their molecular structures and photophysical characteristics revealed that the presence of an electron-rich 4-dimethylaminophenyl donor moiety in compound Nap1 could endow it with a red emission (e.g., λPLmax = 641 nm in the host-guest blend film with a 14 wt% guest composition); moreover, the replacement of the n-hexyl group of Nap1 bonding to the imide nitrogen atom for a more bulky 2,6-di(isopropyl)phenyl one would result in compound Nap2 with more alleviated concentration quenching. Alteration of the 4-(dimethylamino)phenyl donor subunit of Nap2 into a more electron-donating 1,1,7,7-tetramethyljulolidin-9-yl substituent would render compound Nap3 with more improved chromaticity (e.g., λPLmax = 663 nm in a 14 wt% guest-doped film). Consequently, Nap3 could not only emit standard-red fluorescence with satisfactory chromaticity, but it also showed suppressed intermolecular interactions. Using Nap3 as the dopant, a heavily doped standard-red organic light-emitting diode (OLED) with the device configuration of ITO/MoO3 (1 nm)/TcTa (40 nm)/CzPhONI:Nap3 (14 wt%) (20 nm)/TPBI (45 nm)/LiF (1 nm)/Al (80 nm) was fabricated, and the Commission Internationale de L'Eclairage coordinates, maximum external quantum efficiency and maximum current efficiency of this OLED were (0.67,0.32), 1.8% and 0.7 cd A-1, respectively. All these preliminary results indicated that 1,8-naphthalimide derivatives could act as quite promising standard-red light-emitting materials for OLED applications. This journal is
In-situ facile synthesis novel N-doped thin graphene layer encapsulated Pd@N/C catalyst for semi-hydrogenation of alkynes
Lin, Shanshan,Liu, Jianguo,Ma, Longlong,Sun, Jiangming
, (2021/12/03)
Transition metal-catalyzed semi-hydrogenation of alkynes has become one of the most popular methods for alkene synthesis. Specifically, the noble metal Pd, Rh, and Ru-based heterogeneous catalysts have been widely studied and utilized in both academia and industry. But the supported noble metal catalysts are generally suffering from leaching or aggregation during harsh reaction conditions, which resulting low catalytic reactivity and stability. Herein, we reported the facile synthesis of nitrogen doped graphene encapsulated Pd catalyst and its application in the chemo-selective semi-hydrogenation of alkynes. The graphene layer served as “bulletproof” over the active Pd Nano metal species, which was confirmed by X-ray and TEM analysis, enhanced the catalytic stability during the reaction conditions. The optimized prepared Pd@N/C catalyst showed excellent efficiency in semi-hydrogenation of phenylacetylene and other types of alkynes with un-functionalized or functionalized substituents, including the hydrogenation sensitive functional groups (NO2, ester, and halogen).
Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy
Alansari, Isabella Y.,Clark, Joseph R.,Holdren, Martin S.,Neill, Justin L.,Pate, Brooks H.,Reyes, Albert,Sloane, Samantha E.,Sonstrom, Reilly E.,Vang, Zoua Pa
supporting information, p. 7707 - 7718 (2021/06/21)
A copper-catalyzed alkene transfer hydrodeuteration reaction that selectively incorporates one hydrogen and one deuterium atom across an aryl alkene is described. The transfer hydrodeuteration protocol is selective across a variety of internal and terminal alkenes and is also demonstrated on an alkene-containing complex natural product analog. Beyond using 1H, 2H, and 13C NMR analysis to measure reaction selectivity, six transfer hydrodeuteration products were analyzed by molecular rotational resonance (MRR) spectroscopy. The application of MRR spectroscopy to the analysis of isotopic impurities in deuteration chemistry is further explored through a measurement methodology that is compatible with high-throughput sample analysis. In the first step, the MRR spectroscopy signatures of all isotopic variants accessible in the reaction chemistry are analyzed using a broadband chirped-pulse Fourier transform microwave spectrometer. With the signatures in hand, measurement scripts are created to quantitatively analyze the sample composition using a commercial cavity enhanced MRR spectrometer. The sample consumption is below 10 mg with analysis times on the order of 10 min using this instrument - both representing order-of-magnitude reduction compared to broadband MRR spectroscopy. To date, these measurements represent the most precise spectroscopic determination of selectivity in a transfer hydrodeuteration reaction and confirm that product regioselectivity ratios of >140:1 are achievable under this mild protocol.
Chemical Targeting of Voltage Sensitive Dyes to Specific Cells and Molecules in the Brain
Fiala, Tomas,Wang, Jihang,Dunn, Matthew,?ebej, Peter,Choi, Se Joon,Nwadibia, Ekeoma C.,Fialova, Eva,Martinez, Diana M.,Cheetham, Claire E.,Fogle, Keri J.,Palladino, Michael J.,Freyberg, Zachary,Sulzer, David,Sames, Dalibor
supporting information, p. 9285 - 9301 (2020/06/04)
Voltage sensitive fluorescent dyes (VSDs) are important tools for probing signal transduction in neurons and other excitable cells. The impact of these highly lipophilic sensors has, however, been limited due to the lack of cell-specific targeting methods in brain tissue or living animals. We address this key challenge by introducing a nongenetic molecular platform for cell- and molecule-specific targeting of synthetic VSDs in the brain. We employ a dextran polymer particle to overcome the inherent lipophilicity of VSDs by dynamic encapsulation and high-affinity ligands to target the construct to specific neuronal cells utilizing only native components of the neurotransmission machinery at physiological expression levels. Dichloropane, a monoamine transporter ligand, enables targeting of dense dopaminergic axons in the mouse striatum and sparse noradrenergic axons in the mouse cortex in acute brain slices. PFQX in conjunction with ligand-directed acyl imidazole chemistry enables covalent labeling of AMPA-type glutamate receptors in the same brain regions. Probe variants bearing either a classical electrochromic ANEP dye or state-of-the-art VoltageFluor-type dye respond to membrane potential changes in a similar manner to the parent dyes, as shown by whole-cell patch recording. We demonstrate the feasibility of optical voltage recording with our probes in brain tissue with one-photon and two-photon fluorescence microscopy and define the signal limits of optical voltage imaging with synthetic sensors under a low photon budget determined by the native expression levels of the target proteins. This work demonstrates the feasibility of a chemical targeting approach and expands the possibilities of cell-specific imaging and pharmacology.