870259-02-2Relevant articles and documents
Simply planarizing nonfused perylene diimide based acceptors toward promising non-fullerene solar cells
Bian, Gao-Feng,Zhao, Feng,Lau, Tsz-Ki,Sheng, Chun-Qi,Lu, Xinhui,Du, Hui,Zhang, Cheng,Qu, Zhi-Rong,Chen, Hongzheng,Wan, Jun-Hua
, p. 8092 - 8100 (2019)
This work focuses on developing high-efficiency perylene diimide (PDI)-based small molecular nonfullerene acceptors with a simple synthetic strategy. We reported a new electron acceptor, Py-e-PDI, obtained via cross-coupling four PDI units with a planar pyrene core through ethynyl groups. Although the ring-fusion synthetic procedure was omitted, the large planar core and significantly reduced intramolecular steric hindrance endowed this nonfused PDI-tetramer derivative with moderate planarity. Differing from most of the PDI-tetramers with highly twisted geometries, Py-e-PDI could self-assemble into a highly ordered structure. The inverted solar cells with PTB7-Th/Py-e-PDI blends exhibited the best power conversion efficiency of up to 7.59%, which mainly resulted from the combined contribution of complementary absorption with a donor polymer, desirable aggregation and high electron mobility. Most importantly, this result demonstrates that simply planarizing 3D nonfused perylene diimide based acceptors is effective to improve the performance of the corresponding non-fullerene (NF) acceptors.
Pyrene-containing conjugated organic microporous polymers for photocatalytic hydrogen evolution from water
Mohamed, Mohamed Gamal,Elsayed, Mohamed Hammad,Elewa, Ahmed M.,EL-Mahdy, Ahmed F. M.,Yang, Cheng-Han,Mohammed, Ahmed A. K.,Chou, Ho-Hsiu,Kuo, Shiao-Wei
, p. 2229 - 2241 (2021/04/09)
Photoactive conjugated microporous polymers (CMPs) are emerging as porous materials capable of mediating the photocatalytic evolution of H2from water. In this study, we synthesized three pyrene-based CMPs (Py-F-CMP, Py-TPA-CMP, Py-TPE-CMP) through Sonogashira-Hagihara cross-couplings of 1,3,6,8-tetraethynylpyrene (Py-T, as a common monomer building block) with 2,7-dibromo-9H-fluorene (F-Br2), tris(4-bromophenyl)amine (TPA-Br3), and 1,1,2,2-tetrakis(4-bromophenyl)ethene (TPE-Br4), respectively, in the presence of Pd(PPh3)4in DMF/Et3N. We then characterized the chemical structures, crystallinities, thermal stabilities, surface morphologies, and porosities of these three new CMPs. Brunauer-Emmett-Teller (BET) analyses and tests of photocatalytic H2production revealed that Py-TPA-CMP displayed the highest BET surface area (454 m2g?1), highest total pore volume (0.28 cm3g?1), highest H2evolution rate (19?200 μmol h?1g?1), and highest apparent quantum yield (15.3%) when compared with those of Py-F-CMP, Py-TPE-CMP, and other organic porous materials.
Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions
Maeda, Hajime,Tanaka, Kazuhiro,Aratani, Mona,Segi, Masahito
, p. 762 - 772 (2019/01/16)
Substances containing ethynylpyrenes linked to either one or four benzocrown ethers were synthesized, and their absorption and fluorescence spectroscopic responses to metal ions were assessed. Addition of metal perchlorates to solutions of these substances promotes short wavelength shifts in their absorption and fluorescence maxima and increases in their fluorescence intensities. The magnitudes of the fluorescence intensity increases are dependent on the ring size and number of the crown ether and the nature of the metal cation. Association constants for complex formation were calculated using fluorescence intensity versus concentration data. Analysis using Job's plots showed that the substances containing one benzocrown ether moiety form 1:1 complexes with metal ions. Results of experiments employing repeated addition and removal of Mg(ClO4)2 demonstrate that the ON-OFF fluorescence response can be repeated at least three times. Results of molecular orbital calculations show that complexation with metal ions lowers the energies of both the π and π* levels of the ethynylpyrene moiety and that in some cases the vacant orbital on the metal becomes the LUMO of the complex. An explanation of the spectroscopic changes promoted by metal ions is proposed in terms of electrostatic repulsion and structural regulation.
Starburst non-fullerene organic small molecule receptor material containing pyrene and perylene diimide and preparation method of starburst non-fullerene organic small molecule receptor material
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Paragraph 0035; 0037; 0040; 0041, (2019/06/07)
The invention discloses a starburst non-fullerene organic small molecule receptor material containing pyrene and perylene diimide and a preparation method of the starburst non-fullerene organic smallmolecule receptor material. The non-fullerene organic small molecule receptor material is bridged with condensed nucleus pyrene and perylene bisimide units through triple bonds, the obtained materialhas good thermal stability, raw materials are common and easy to obtain and can be purified through recrystallization, and the production cost is low; and the starburst non-fullerene organic small molecule receptor material is applied to a polymer solar cell, the effect with the energy conversion efficiency being 6-8% can be achieved under the condition of an optimizing device, the starburst non-fullerene organic small molecule receptor material serves as a third component to be added into a ternary solar cell active layer, the density of a short-circuit current of the ternary solar cell active layer can be remarkably increased, the effect with the energy conversion efficiency being 8-11% can be achieved, and certain practical application value is achieved.
A graphdiyne-based carbon material for electroless deposition and stabilization of sub-nanometric Pd catalysts with extremely high catalytic activity
Yang, Liang-Liang,Wang, Hong-Juan,Wang, Juan,Li, Yu,Zhang, Wen,Lu, Tong-Bu
supporting information, p. 13142 - 13148 (2019/06/13)
The development of sub-nanometric metal particles (1 nm) as advanced heterogeneous catalysts has received considerable interest due to their outstanding catalytic performance, while the synthesis and stabilization of sub-nanometric catalysts (SNCs) without using additional surface capping agents remains a challenge. Herein, we report the synthesis of novel three-dimensional pyrenyl graphdiyne (Pyr-GDY) ultrafine nanofibers (3-10 nm), which can serve as an ideal substrate for electroless deposition and stabilization of Pd SNCs through the terminal uncoupled acetenyl groups in Pyr-GDY, with an average Pd particle size of only 0.83 nm. The as-synthesized Pd/Pyr-GDY composite shows extremely high catalytic activities for the reduction of nitroarenes to arylamines and Suzuki coupling reactions, 300 and 25 times higher than those of commercial Pd/C, respectively. The outstanding catalytic performance can be ascribed to the sub-nanometric Pd particles with a "clean surface", and the unique three-dimensional network structure of Pyr-GDY, being favorable for rapid mass transfer. Our result provides an ideal carbon material for electroless deposition and stabilization of other SNCs with a "clean surface", which will display outstanding catalytic activity for various catalytic reactions.
Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene
Cappellari, Maria V.,Mangione, María I.,Spanevello, Rolando A.,Marzari, Gabriela,Morales, Gustavo M.,Fungo, Fernando
, p. G163 - G170 (2019/05/21)
The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices.
Effects of substituents on silicon atoms upon absorption and fluorescence properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes
Maeda, Hajime,Shoji, Tomokazu,Segi, Masahito
, p. 4372 - 4376 (2017/10/23)
Synthesis, UV–vis absorption, and fluorescence spectroscopic properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes 2–10 were studied. Absorption maxima of CH2Cl2 solutions of these compounds appeared at 437–445 nm, and molar absorption coefficients (ε) of most of these compounds exceeded 105 L mol?1 cm?1. Fluorescence emissions measured in dilute CH2Cl2 solutions are observed in visible region, and their intensities remarkably increased compared with that of pyrene. Fluorescence spectra obtained from concentrated CH2Cl2 solutions exhibited broad excimer emissions when steric bulk of substituents on silicon atoms is sufficiently low. Molecular orbital calculations indicated that HOMO-LUMO energy gap decreased with increasing the number of phenyl groups on silicon atoms, and that the silyl groups act as electron-donating groups to tetraethynylpyrene core. Resonances in 29Si NMR spectra shifts to upfield with increasing the number of phenyl groups on silicon atoms due to the shielding effect of phenyl groups.
BODIPY-containing porous organic polymers for gas adsorption
Xu, Yunfeng,Chang, Dan,Feng, Shi,Zhang, Chong,Jiang, Jia-Xing
, p. 9415 - 9423 (2016/11/11)
A series of BODIPY-containing microporous organic polymers was synthesized via a Sonogashira-Hagihara cross-coupling reaction of a BODIPY derivative with triple polymerisable groups and a range of aryl-alkyne monomers. All of the polymers show high isosteric heats of CO2 adsorption (23.3-27.3 kJ mol-1) because the incorporation of heteroatoms (N, B, F) from the BODIPY unit into the polymer skeleton enhanced the binding affinity between the pore wall and CO2 molecules. The aryl-alkyne monomer has a large influence on the surface area and CO2 adsorption performance of the resulting polymers. The polymer BDPCMP-3 shows a high Brunauer-Emmett-Teller specific surface area of up to 725 m2 g-1, while BDPCMP-2 with a low surface area of 582 m2 g-1 shows a high CO2 uptake ability of 2.25 mmol g-1 at 1.13 bar/273 K with a CO2/N2 adsorption selectivity of 32.3.
Design and preparation of platinum-acetylide organogelators containing ethynyl-pyrene moieties as the main skeleton
Xu, Xing-Dong,Zhang, Jing,Yu, Xudong,Chen, Li-Jun,Wang, De-Xian,Yi, Tao,Li, Fuyou,Yang, Hai-Bo
, p. 16000 - 16013 (2013/02/23)
A series of new platinum-acetylide complexes containing ethynyl-pyrene moieties as the main skeleton were synthesized and characterized. The investigation of the absorption and emission spectra of these complexes revealed that the extension of the molecular size with the introduction of different numbered platinum-acetylide fragments can efficiently tune the absorption and emission bands from the UV to the longer wavelength region. Moreover, the gelation properties of these complexes were investigated by the "stable-to-inversion-of-a-test-tube" method. Most newly designed platinum-acetylide compounds presented a stable gel-formation property in some of the tested solvents. The morphology of the xerogels was investigated by scanning electron microscopy (SEM). Furthermore, the concentration- and temperature-dependent absorption and emission properties of these complexes were investigated, which support the formation of J-type assemblies during the aggregation process. More importantly, it was found that the complexes 4 a-C6, 4 a, and 4 a-C18 with four platinum-acetylide fragments presented potential applications as luminescent organometallic gels.
Synthesis and hole transport properties of highly soluble pyrene-based discotic liquid crystals with trialkylsilylethynyl groups
Hirose, Takuji,Shibano, Yuki,Miyazaki, Yutaro,Sogoshi, Norihito,Nakabayashi, Seiichiro,Yasutake, Mikio
experimental part, p. 81 - 92 (2011/10/03)
Four pyrene-based discotic compounds with trialkylsilylethynyl groups in the side chains were prepared and characterized by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. All of the compounds were hig
