1498-83-5Relevant academic research and scientific papers
Functional Platinum(II) Complexes with Four-Photon Absorption Activity, Lysosome Specificity, and Precise Cancer Therapy
Zhang, Qiong,Wang, Shujing,Zhu, Yingzhong,Zhang, Chengkai,Cao, Hongzhi,Ma, Wen,Tian, Xiaohe,Wu, Jieying,Zhou, Hongping,Tian, Yupeng
, p. 2362 - 2371 (2021)
Multiphoton materials are in special demand in the field of photodynamic therapy and multiphoton fluorescence imaging. However, rational design methodology for these brands of materials is still nascent. This is despite transition-metal complexes favoring optimized nonlinear-optical (NLO) activity and heavy-atom-effected phosphorescent emission. Here, three four-photon absorption (4PA) platinum(II) complexes (Pt1-Pt3) are achieved by the incorporation of varied functionalized C^N^C ligands with high yields. Pt1-Pt3 exhibit triplet metal-to-ligand charge-transfer transitions at ~460 nm, which are verified multiple times by transient absorption spectra, time-dependent density functional theory calculations, and low-temperature emission spectra. Further, Pt1-Pt3 undergo 4PA. Notably, one of the complexes, Pt2, has maximum 4PA cross-sectional values of up to 15.2 × 10-82 cm8 s3 photon-3 under excitation of a 1600 nm femtosecond laser (near-IR II window). The 4PA cross sections vary when Pt2 is binding to lecithin and when it displays its lysosome-specific targeting behavior. On the basis of the excellent 4PA property of Pt2, we believe that those 4PA platinum(II) complexes have great potential applications in cancer theranostics.
TMSOTf-mediated Kr?hnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
Chan, Chieh-Kai,Chung, Yi-Hsiu,Wang, Cheng-Chung
, p. 8263 - 8273 (2022/04/07)
An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid additive to Sn(OTf)2, and the desired product was also confirmed using X-ray single-crystal diffraction analysis.
Synthesis of Kr?hnke pyridines through iron-catalyzed oxidative condensation/double alkynylation/amination cascade strategy
Gopalaiah, Kovuru,Choudhary, Renu
supporting information, (2021/09/15)
An efficient protocol for the synthesis of symmetrical and unsymmetrical 2,4,6-trisubstituted pyridines via oxidative cascade annulation of arylacetylenes with benzylamines has been developed. The reaction proceeds smoothly utilizing iron(II) triflate as a catalyst and molecular oxygen as an oxidant with broad substrate scope. Mechanistic studies reveal that the reaction may be experiences an oxidative condensation followed by double alkynylation and amination process.
Copper-catalyzed efficient access to 2,4,6-triphenyl pyridinesviaoxidative decarboxylative coupling of aryl acetic acids with oxime acetates
Bharat Kumar, Karasala,Chinnari, Lekkala,Shyamala, Pulipaka,Siddaiah, Vidavalur,Varaprasad, Bodala
supporting information, p. 15205 - 15209 (2021/09/06)
An efficient and concise approach for the synthesis of 2,4,6-triphenyl pyridines has been developed through copper-catalysed oxidative decarboxylative coupling of C(sp3) aryl acetic acids with oxime acetates in DMF at 150 °C under an oxygen atm
Design and application of (Fe3O4)-GOTfOH based AgNPs doped starch/PEG-poly (acrylic acid) nanocomposite as the magnetic nanocatalyst and the wound dress
Forouzandehdel, Shayan,Meskini, Maryam,Rami, Mina Rezghi
, (2020/04/21)
As a novel, recyclable nanocatalyst, (Fe3O4)-GOTfOH based Ag nanoparticles doped Starch/PEG-poly (acrylic acid) nanocomposite (Fe3O4?GOTfOH/Ag/St-PEG-AcA) was applied for one-pot synthesis
Cyclometalated pt complexes of cnc pincer ligands: Luminescence and cytotoxic evaluation
Garbe, Simon,Krause, Maren,Klimpel, Annika,Neundorf, Ines,Lippmann, Petra,Ott, Ingo,Brünink, Dana,Strassert, Cristian A.,Doltsinis, Nikos L.,Klein, Axel
supporting information, p. 746 - 756 (2020/03/30)
In the framework of our attempts to develop cyclometalated Pt(II) complexes toward bifunctional targeting inhibitors or agents for photodynamic therapy, diagnostics, and bioimaging, a series of bis-cyclometalated Pt(II) complexes [Pt(CNC)(L)] (L = DMSO, MeCN) containing various (CNC)2- ligands based on 2,6-diphenylpyridine were synthesized and characterized analytically and spectroscopically, focusing on their electrochemical, luminescence, and antiproliferative properties. Electrochemical experiments and UV-vis absorption spectroscopy suggest ligand-centered LUMOs and metal-centered HOMOs in line with DFT calculations. Extension of the ancillary phenyl to naphthyl cores and a central 4-phenylpyridine group instead of pyridine results in bathochromic shifts of the long-wavelength absorption bands ranging from 420 to 440 nm, with the latter shift being more pronounced. The complexes of the fused CNC heterocyclic systems dba (H2dba = dibenzo[c,h]acridine), db(ph)a (H2db(ph)a = 7-phenyldibenzo[c,h]acridine), and bzqph (HbzqphH = 2-phenylbenzo[h]quinoline) absorb far more red-shifted in the range 500-530 nm. All complexes show reversible first electrochemical reductions and irreversible oxidations with an electrochemical gap of about 3 V, roughly in line with the absorption energies. While the 2,6-diphenylpyridine complexes [Pt(CNC)(DMSO)] show no luminescence at ambient temperature in solution, the fused dba, db(ph)a, and bzqph derivatives are efficient triplet emitters at ambient temperature with emission wavelengths in the region 575-600 nm and quantum yields ranging from 7 to 23%. Vibrationally resolved emission spectra calculated in the framework of DFT faithfully reproduce the experimental data. TD-DFT calculations at the excited-state T1 geometry reveal intraligand π-π*/MLCT character of the emission for all three investigated complexes. Antiproliferative tests on selected complexes gave very different toxicities, ranging from lower than 1 μM to virtually nontoxic. The data allowed drawing some structure-activity relationships (SAR), even though variations in solubility could also significantly account for the different toxicities.
Synthesis of triphenylpyridines: Via an oxidative cyclization reaction using Sr-doped LaCoO3 perovskite as a recyclable heterogeneous catalyst
Le, Thu N. M.,Doan, Son H.,Pham, Phuc H.,Trinh, Khang H.,Huynh, Tien V.,Tran, Tien T. T.,Le, Minh-Vien,Nguyen, Tung T.,Phan, Nam T. S.
, p. 23876 - 23887 (2019/08/12)
An La0.6Sr0.4CoO3 strontium-doped lanthanum cobaltite perovskite was prepared via a gelation and calcination approach and used as a heterogeneous catalyst for the synthesis of triphenylpyridines via the cyclization reactio
A New Synthetic Pathway to Triphenylpyridines via Cascade Reactions Utilizing a New Iron-Organic Framework as a Recyclable Heterogeneous Catalyst
Doan, Son H.,Tran, Nhu K. Q.,Pham, Phuc H.,Nguyen, Vu H. H.,Nguyen, Ngoc N.,Ha, Phuong T. M.,Li, Shuang,Le, Ha V.,Le, Nhan T. H.,Tu, Thach N.,Phan, Nam T. S.
supporting information, p. 2382 - 2389 (2019/03/27)
A new iron-organic framework, VNU-22 {[Fe3(BTC)(BPDC)2]·11.97H2O}, constructed from BTC3–, BPDC2– pillars and infinite [Fe3(CO2)7]∞ rod SBU, was obtained. The VNU-22 was utilized as a heterogeneous catalyst in the synthesis of 2,4,6-triphenylpyridines via cascade reactions from acetophenones and phenylacetic acids with ammonium acetate as a nitrogen source. This transformation is new. The VNU-22 was more active in the cascade reactions than many homogeneous and heterogeneous catalysts. The framework catalyst was recovered and reutilized without an appreciable decline in its performance. To our best knowledge, this synthetic pathway to 2,4,6-triphenylpyridines was not previously reported, and would attract interests from the chemical industry.
Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines
Yang, Qing,Zhang, Yilin,Zeng, Wei,Duan, Zheng-Chao,Sang, Xinxin,Wang, Dawei
supporting information, p. 5683 - 5690 (2019/10/22)
Metal-free, base-free, biomimetic and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed under mild conditions for the first time. The heterogeneous biomimetic catalyst-recoverable Merrifield resin-supported quinone-was fully characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectrometry (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported quinone catalyst exhibited excellent catalytic reactivity for chemoselective synthesis of 2,4,6-trisubstituted pyridines, providing an efficient and green method for the synthesis of pyridine derivatives under mild conditions. Mechanistic investigations were conducted to gain insights into the heterogeneous biomimetic catalyst as well as the resulting transformation. The successful capture of intermediates offered direct and clear evidence for the proposed mechanism.
An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions
Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
, p. 5158 - 5163 (2019/02/27)
A simple and efficient protocol developed for one pot three-component synthesis of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate using the versatile super Br?nsted acid triflimide (HNTf2) as an effective catalyst is described. The reactions proceed well in the presence of 1 mol% of HNTf2 at 80 °c under solvent-free conditions and provide the corresponding triarylpyridines in good to excellent yields. The method reported has several advantages such as a metal-free and commercially available catalyst, mild reaction conditions and lower loading of catalyst.
