330-91-6Relevant academic research and scientific papers
Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
, p. 403 - 413 (2020/12/23)
A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer
Akwii, Racheal,Alvina, Karina,Ashraf-Uz-Zaman, Md,Farshbaf, Mohammad Jodeiri,German, Nadezhda A.,Kallem, Raja Reddy,Mikelis, Constantinos M.,Putnam, William,Sajib, Md Sanaullah,Shahi, Sadisna,Trippier, Paul C.,Wang, Wei,Zhang, Ruiwen
supporting information, (2020/10/12)
Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.
ORGANIC COMPOUNDS, LIGHT EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS
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Paragraph 0214; 0219-0222, (2020/08/07)
The present invention relates to an organic compound having a condensed aromatic core with a fluorene moiety and substituted with one or more functional groups having excellent hole transport properties, and a light emitting diode and a light emitting device using the same. According to the present invention, the organic compound can be introduced into a light emitting diode by using a solution process, and has a very deep HOMO energy level. When the organic compound of the present invention is applied to a hole transport layer, a band gap of the HOMO energy level between the hole transport layer and a light emitting material layer can be reduced, and thus holes and electrons can be injected into the light emitting material layer in a balanced manner. Accordingly, the light emitting diode and the light emitting device capable of low-voltage driving with higher light emitting efficiency can be implemented.COPYRIGHT KIPO 2020
Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning
Ahn, Mina,Kim, Min-Ji,Wee, Kyung-Ryang
, p. 12050 - 12057 (2019/10/11)
A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), was synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regard to the electron push-pull substituent effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, a different charge-transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron-withdrawing group of CN-substituted 2a did not correlate with the other R group compounds. From the experimental data and density functional theory calculations, we assume that there is a constraint on emission color tuning to generate higher energy of blue emission in the D-A-D molecular system, due to the reverse charge-transfer property caused by the strong electron-withdrawing group.
Tuning the Photophysical Properties of Symmetric Squarylium Dyes: Investigation on the Halogen Modulation Effects
Chen, Weiben,Zhang, Simeng,Dai, Gaole,Chen, Ying,Li, Miao,Zhao, Xiaoyu,Chen, Yulan,Chen, Long
supporting information, p. 469 - 473 (2019/01/04)
A series of symmetric squarylium dyes (SQDPA-X) with different halogen (X=F, Cl, Br, I) substituents have been developed. The photophysical properties could be facilely tuned by the halogen modulation effects. The strategy of incorporating different halogen substitutions into AIE active luminogens enables a facile approach for exploring new intriguing organic fluorescent dyes.
Analogs of penfluridol as chemotherapeutic agents with reduced central nervous system activity
Ashraf-Uz-Zaman, Md,Sajib, Md Sanaullah,Cucullo, Luca,Mikelis, Constantinos M.,German, Nadezhda A.
supporting information, p. 3652 - 3657 (2018/11/03)
Several recent reports have highlighted the feasibility of the use of penfluridol, a well-known antipsychotic agent, as a chemotherapeutic agent. In vivo experiments have confirmed the cytotoxic activity of penfluridol in triple-negative breast cancer model, lung cancer model, and further studies have been proposed to assess its anticancer activity and viability for the treatment of glioblastomas. However, penfluridol anticancer activity was observed at a dosage significantly higher than that administered in antipsychotic therapy, thus raising the concern for the potential onset of CNS side effects in patients undergoing intensive pharmacological treatment. In this study, we evaluate the potential CNS toxicity of penfluridol side by side with a set of analogs.
An electroluminescent compound and an electroluminescent device comprising the same
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Paragraph 0088-0091; 0109-0112; 0154-0157, (2016/10/20)
The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1. In the case of adopting the same as a dopant compound or a hole transfer compound in a luminous layer, an organic electroluminescent device having excellent luminous characteristics such as driving voltage, brightness, long lifespan, and the like, can be embodied.COPYRIGHT KIPO 2016
Synthesis of benzo-γ-sultams via the Rh-catalyzed aromatic C-H functionalization of diazosulfonamides
Yang, Zhanhui,Xu, Jiaxi
supporting information, p. 3616 - 3618 (2014/04/03)
An efficient synthesis of 1-aryl-benzo-γ-sultams, 1-aryl-1,3-dihydrobenzo[c]isothiazole-2,2-dioxides, was achieved in 65-99% yields via the Rh-catalyzed intramolecular aromatic C-H functionalization of N,N-diaryl diazosulfonamides with 0.5 mol% Rh2(oct)4 as the catalyst. This journal is the Partner Organisations 2014.
O-iodoxybenzoic acid mediated N-arylation of aromatic amines by using arylhydrazines as the arylating counterpart
Jadhav, Ravindra R.,Huddar, Sameerana N.,Akamanchi, Krishnacharya G.
supporting information, p. 6779 - 6783 (2013/11/06)
Through free-radical trapping experiments we have established, for the first time, the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation of aryl free radicals. On the basis of this finding, a method was developed for the N-arylation of aromatic amines under mild conditions (base-free, -5 °C) by using arylhydrazines as the arylating counterpart and arylamines. The scope of this method was demonstrated by using a number of arylhydrazines and arylamines, which gave the N-arylated amines in good yields. Through free-radical trapping experiments, the present work describes the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation aryl free radicals. This finding is exploited in the development of a mild method for the N-arylation of arylamines by using arylhydrazines as the arylating agents. The scope of this method is demonstrated through a number of examples. Copyright
Selective one-pot synthesis of symmetrical and unsymmetrical di- and triarylamines with a ligandless copper catalytic system
Tlili, Anis,Monnier, Florian,Taillefer, Marc
supporting information; experimental part, p. 6408 - 6410 (2012/07/27)
The one-pot synthesis of symmetrical or unsymmetrical di- or triarylamines using aryl iodides or bromides and LiNH2 as ammonia source is reported. This highly selective method is based, for the first time, on a copper-catalyzed system, which does not require the presence of any additional ligand.
