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.
An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond
Lu, Lingxiang,Siu, Juno C.,Lai, Yihuan,Lin, Song
supporting information, p. 21272 - 21278 (2020/12/21)
The construction of C(sp3)-Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si-Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.
