2350-01-8Relevant articles and documents
Small-molecule azomethines: Organic photovoltaics via Schiff base condensation chemistry
Petrus,Bouwer,Lafont,Athanasopoulos,Greenham,Dingemans
, p. 9474 - 9477 (2014)
Conjugated small-molecule azomethines for photovoltaic applications were prepared via Schiff base condensation chemistry. Bulk heterojunction (BHJ) devices exhibit efficiencies of 1.2% with MoOx as the hole-transporting layer. The versatility and simplicity of the chemistry is illustrated by preparing a photovoltaic device directly from the reaction mixture without any form of workup. This journal is the Partner Organisations 2014.
A Schiff base based on triphenylamine and thiophene moieties as a fluorescent sensor for Cr (III) ions: Synthesis, characterization and fluorescent applications
Erdener, Di?dem,Kaya, ?smet,Kolcu, Feyza
, (2020)
A Schiff base fluorescent sensor was designed for selective detection of Cr3+ ions in aqueous solution. The procedure for the study was fulfilled in three steps which comprised the synthesis of 4-nitro-triphenylamine (TPA-NO2), 4-amino-triphenylamine (TPA-NH2) and Schiff base (TPA-Th) using 2,2′-bithiophene-5-carboxaldehyde, respectively. Structural characterization of the purely synthesized compounds was acquired by using UV–Vis, FT-IR, 1H NMR and 13C NMR analyses. Their electrochemical, thermal, and the optical sensor properties for metal ions were enlightened by cyclic voltammetry (CV), thermal-TG-DTA and photoluminescence (PL) techniques, respectively. Non-fluorescent TPA-Th displayed a fluorescence enhancement after chelation with Cr3+ ions with high selectivity and overall emission change of 59-fold at an excitation wavelength of 320 nm. The limit of detection (LOD) value was as low as 1.5 × 10?6 M for Cr3+ ions, accompanied by an association constant (Ka) of 2.8 × 104 M?1. TPA-Th was beneficial for the design and development of metal-complexed fluorescent sensor and light emitting devices.
Enhanced lifetime of organic light-emitting diodes using an anthracene derivative with high glass transition temperature
Lee, Seung-Hun,Kim, Sung Hyun,Kwak, Jeonghun
, p. 4216 - 4222 (2013)
Highly stable and efficient phosphorescent organic light-emitting diodes (OLEDs) were demonstrated by using anthracene-based hole injection buffer layer possessing high glass transition temperature. We synthesized a new anthracene derivative, 9,10-bis(3,3′-(N′,N′-diphenyl-(Nnaphthalene- 2-yl)benzene-1,4-diamine) phenyl)anthracene (TANPA) and characterized its optical and thermal properties. It showed high glass transition temperature of 154 °C which could be attributed to the insertion of anthracene into the aromatic amino group with triphenylamine. We also utilized TANPA for the hole injection and transport layers in phosphorescent OLEDs. Since TANPA has high glass transition temperature, the OLEDs using this material exhibited higher operational stability compared to the device without TANPA. When we use TANPA as the hole injection layer in combination with a widely-used hole transporting material, N,N′-di(1-naphthyl)-N,N-diphenylbenzidine (NPB), the devices showed high enhancement in terms of the operational lifetime, driving voltage change, and device efficiency, originating from the electron-hole charge balance as well as good thermal stability of TANPA. Copyright
Organic dyes containing nonsubstituted aryl amino moieties and azobenzene units for dye-sensitized solar cells
Toan, Nguyen Duc,Chiu, Kuo Yuan,Tran, Thai Thi Ha,Yang, Te-Fang,Su, Yuhlong Oliver
, p. 1172 - 1177 (2019)
A series of novel sensitizers were successfully synthesized utilizing azobenzene as a π-linkage unit for the D–π–A structure. A slight red shift on the absorption spectra and λonset of the sensitizers could be observed when the thienyl group was introduced to the acceptor moiety (A). In addition, replacing the donor moiety (D) from carbazole to diarylamino could lead to a negative shift (approximately 0.3 V) in the first oxidation potential. DFT calculation was also carried out and the trend of calculated HOMO–LUMO gaps was consistent to the experimental data obtained from the CV results (DT1 DT2 DT3 DT4). These sensitizers were then employed in dye-sensitized solar cells to investigate their photovoltaic performances. Highest power conversion efficiency (PCE) of 0.84% was achieved for DT1-based DSSC according to its most bathochromic absorption spectrum.
Conjugated donor-acceptor-acceptor (D-A-A) molecule for organic nonvolatile resistor memory
Dong, Lei,Li, Guangwu,Yu, An-Dih,Bo, Zhishan,Liu, Cheng-Liang,Chen, Wen-Chang
, p. 3403 - 3407 (2014)
A new donor-acceptor-acceptor (D-A-A) type of conjugated molecule, N-(4-(N′,N′-diphenyl)phenylamine)-4-(4′-(2,2-dicyanovinyl)phenyl) naphthalene-1,8-dicarboxylic monoimide (TPA-NI-DCN), consisting of triphenylamine (TPA) donors and naphthalimide (NI)/dicyanovinylene (DCN) acceptors was synthesized and characterized. In conjunction with previously reported D-A based materials, the additional DCN moiety attached as end group in the D-A-A configuration can result in a stable charge transfer (CT) and charge-separated state to maintain the ON state current. The vacuum-deposited TPA-NI-DCN device fabricated as an active memory layer was demonstrated to exhibit writeonce- read-many (WORM) switching characteristics of organic nonvolatile memory due to the strong polarity of the TPA-NI-DCN moiety.
Near-Infrared Boron Difluoride Formazanate Dyes
Buguis, Francis L.,Maar, Ryan R.,Staroverov, Viktor N.,Gilroy, Joe B.
, p. 2854 - 2860 (2021)
Near-infrared (NIR) dyes are sought after for their utility in light harvesting, bioimaging, and light-mediated therapies. Since long-wavelength photoluminescence typically involves extensive π-conjugated systems of double bonds and aromatic rings, it is often assumed that NIR dyes have to be large molecules that require complex syntheses. We challenge this assumption by demonstrating that facile incorporation of tertiary amine groups into readily available 3-cyanoformazans affords efficient production of relatively simple NIR-active BF2 formazanate dyes (λabs=691–760 nm, λPL=834–904 nm in toluene). Cyclic voltammetry experiments on these compounds reveal multiple reversible redox waves linked to the interplay between the tertiary amine and BF2 formazanate moieties. Density-functional calculations indicate that the NIR electronic transitions in BF2 formazanates are of π→π*-type, but do not always involve strong charge transfer.
Non-doped organic light-emitting diodes based on phenanthroimidazole-triphenylamine derivatives with a low efficiency roll-off of 9% at a high luminance of 10?000 cd m-2
Du, Chunya,Feng, Zijun,Gao, Lei,He, Xin,Jiang, Dongyan,Liu, Futong,Liu, Hui,Lu, Ping
, p. 14446 - 14452 (2020)
Simultaneously achieving high exciton utilization efficiency (ηS) and a low efficiency roll-off at high brightness is challenging for fluorescent organic light-emitting diodes (OLEDs). In this work, we tried to realize this goal by constructing "hot exciton"materials by fine-tuning the lowest triplet excited state (T1) features. Two phenanthroimidazole-triphenylamine based donor-acceptor (D-A) derivatives TPPI-AQ and TPPI-BZPCN have been designed and synthesized. The photophysical studies and theoretical calculations reveal that TPPI-BZPCN has an obvious "hot exciton"feature and an aggregation-induced emission (AIE) characteristic. A big gap between T1 and T2 exists in TPPI-BZPCN which provides the possibility for a reverse intersystem system crossing (RISC) process from the upper energy level of T2 to S1. As a result, the non-doped electroluminescent device based on TPPI-BZPCN achieves a maximum external quantum efficiency (EQE) of 3.33%. The electroluminescence (EL) spectrum exhibits an emission peak at 592 nm, and the brightness can be up to 55?657 cd m-2. Also, the device is able to retain an EQE of 3.03% at the high luminance of 10?000 cd m-2, with a very low efficiency roll-off of 9%, which is the lowest efficiency roll-off currently reported in the orange-red emitters based on the "hot exciton"mechanism. Moreover, the ηS of the non-doped device reaches 48%, which exceeds the limitation of 25% in conventional fluorescence OLEDs.
Azobenzene-based Organic Dyes, Preparation Method Thereof, and Dye-sensitized Solar Cells Comprising the Same
-
Paragraph 0141-0142; 0148-0150, (2021/10/05)
An organic dye based on azobenzene (1) represented by chemical formula (azobenzene), a method for preparing the same, and a dye-sensitized solar cell using the same are D, π-A, (1), and 1 (D) in the formula (donor): (R). 1 ) (R)2 ) N - Where it is R. 1 And R2 Is independently hydrogen, a halogen element, a substituted or unsubstituted C1?C20 alkyl, a substituted or unsubstituted C1?C20 alkoxy, a substituted or unsubstituted C4?C10 aryl, or a substituted or unsubstituted C3?C10 heteroaryl. Π (π spacer) is - π1 -(Π)2 )n -Π-π. 1 is possible. A photoisomerization group represented by the formula, wherein the R is the same as defined above. 3 And R4 Is independently hydrogen, a halogen element, a substituted or unsubstituted C1?C4 alkyl, or a substituted or unsubstituted C1?C4 alkoxy. Π π2 is possible. , Where n is R. 5 Is hydrogen, a halogen element, a substituted or unsubstituted C1?C4 alkyl, or a substituted or unsubstituted C1?C4 alkoxy. Here n is a natural number of 0 or 1; FIGS. A (acceptor) Is an anchoring group (Anchoring group); FIGS. The substituent is at least one selected from the group consisting of halogen elements, hydroxy, C1?C3 alkyl, and C1?C3 alkoxy. The hetero atom is at least one selected from the group consisting N, O and S.
Emergence of Aggregation Induced Emission (AIE), Room-Temperature Phosphorescence (RTP), and Multistimuli Response from a Single Organic Luminogen by Directed Structural Modification
Chatterjee, Abhijit,Chatterjee, Joy,Sappati, Subrahmanyam,Sheikh, Tariq,Umesh, Rintu M.,Ambhore, Madan D.,Lahiri, Mayurika,Hazra, Partha
, p. 12832 - 12846 (2021/11/24)
Multifunctional organic luminogens exhibiting simultaneous aggregation induced emission (AIE), room-temperature phosphorescence (RTP), and mechanochromism have recently attracted considerable attention owing to their potential applications in optoelectronics and bioimaging. However, a comprehensive correlation among these three distinguished properties is yet to be unveiled, which will help to decipher defined methodologies to design future generation multifunctional organic materials. Herein, we have demonstrated a route to obtain a multifunctional organic luminogen, starting from an ACQphore (TPANDI) by simple structural engineering. We have shown that a slight reduction in length of the planar acceptor moieties can effectively inhibit the undesirable π-πstacking interaction between molecules in the condensed state and thereby cause an ACQ to AIE type transformation from TPANDI to TPANMI and TPAPMI. Both TPANMI and TPAPMI exhibit RTP properties (even in ambient condition) because of the presence of a reasonably low singlet-triplet energy gap (δEST). In our study, these two luminogens were found to be mechano-inactive. Interestingly, an insertion of cyano-ethylene group and benzene linker in between the triphenylamine and phthalimide moieties introduced another luminogen TPACNPMI, which can simultaneously exhibit AIE, RTP, and mechanochromic properties.
Triphenylamine/carbazole-modified ruthenium(ii) Schiff base compounds: Synthesis, biological activity and organelle targeting
Chen, Shujiao,Ge, Xingxing,Huang, Jie,Liu, Tong,Liu, Xicheng,Liu, Zhe,Shao, Yue,Tian, Laijin,Wang, Qinghui,Yao, Meimei,Yuan, Xiang-Ai
supporting information, p. 8774 - 8784 (2020/07/10)
Four triphenylamine/carbazole-modified half-sandwich ruthenium(ii) compounds [(η6-p-cymene)Ru(N/O^N)Cl]0/+ with Schiff base chelating ligands (N/O^N) are synthesized and characterized. The introduction of Schiff base units effectively increases the antitumor activity of these compounds (IC50: 1.70 ± 0.56-17.75 ± 3.10 μM), which, meanwhile, can inhibit the metastasis of tumor cells effectively. These compounds follow an energy-dependent cellular uptake mechanism, mainly accumulate in lysosomes to destroy their integrity, and then eventually promote apoptosis. In addition, these compounds can induce an increase of intracellular reactive oxygen species (ROS) levels and provide an antitumor mechanism of oxidation, which is confirmed by the decrease of mitochondrial membrane potential (MMP) and the catalytic oxidation of the coenzyme nicotinamide-adenine dinucleotide (NADH). All these indicate that these ruthenium(ii) compounds are expected to be dual-functional antitumor agents: anti-metastasis and lysosomal damage.
