224-53-3Relevant articles and documents
Regioselective Thermal Cyclization of N-Aryl-4-chloro-1-aza-1,3-butadiene Derivatives. A Short and Efficient Synthesis of Dibenzacridines
Kar, Gandi Kumar,Sami, Izhar,Ray, Jayanta Kumar
, p. 1739 - 1742 (1992)
Dibenzacridines have been synthesized in good yields by thermal cyclization (140-180 deg C) of N-aryl-4-chloro-1-aza-1,3-butadiene derivatives followed by dehydrogenation.
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
, 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.
CYCLOMETALLATION. IV. PALLADIUM(II) COMPOUNDS WITH BENZOQUINOLINE AND SUBSTITUTED 2,6-DIARYLPYRIDINES
Selbin, J.,Gutierrez, M. A.
, p. 95 - 104 (2007/10/02)
The first cyclometallated compounds of some 2,6-diarylpyridines (2) and the related ligand, 5,6,8,9-tetrahydrodibenzacridine (3) were prepared and characterized as acetato-bridged palladium(II) dimers: 2.Inseparable isomers (syn,trans
