3230-51-1Relevant articles and documents
Investigation of novel substituted zinc and aluminium phthalocyanines for photodynamic therapy of epithelial breast cancer
Mohammed, Imadadulla,Oluwole, David O.,Nemakal, Manjunatha,Sannegowda, Lokesh Koodlur,Nyokong, Tebello
, (2019)
A series of phthalonitrile ligands were synthesized by nucleophilic substitution reaction using the hydroxyl or sulfanyl group precursors and the nitro moiety of the nitrophthalonitrile to yield corresponding oxy or sulfanyl bridged ligands. These ligands were subsequently subjected to cyclocondensation reaction with diamagnetic metal ions like zinc and aluminium to afford symmetrically substituted zinc and aluminium phthalocyanine (Pc)complexes and polymers. The ligands and Pc complexes were characterized by 1H nuclear magnetic resonance, fourier transform infrared, ultraviolet visible and mass spectrometric techniques. Additionally, thermal gravimetric, and elemental analyzer were used for characterization of the Pc complexes. The photophysical and photochemical behaviour of the Pc complexes were investigated in dimethyl sulfoxide. Additionally, the complexes were tested against epithelial breast cancer cells for photodynamic therapy (PDT)effect. The substituted ZnPc complexes afforded higher singlet oxygen quantum yields as compared to the AlPc analogue. All the complexes showed innocuous invitro dark cytotoxicity and moderate PDT effect.
Additional effect of para-hydroxyl on the reduction potentials of the N-benzylidenebenzenamines
Cao, Chao-Tun,Zhou, Wei,Cao, Chenzhong
, (2019/12/27)
The reduction potential ERed of disubstituted N-benzylidenebenzenamines XArCH NArY (abbreviated as XBAY) is a measure of the electron acceptance ability of the Lowest-energy Unoccupied Molecular Orbital (LUMO) in molecule, which is closely related to the electronic effects of substituents X and Y in molecule. Previous studies on the ERed of XBAY reported by Luo, Wang, and Yuan all did not involve these molecules containing hydroxyl. In this work, 28 samples of disubstituted N-benzylidenebenzenamines containing para-hydroxyl, (abbreviated as 4-OHBAY or XBAOH-4′) were synthesized, and their ERed values were measured. Then, 127 compounds were taken as a complicated ERed data set, which involved 28 compounds (4-OHBAY and XBAOH-4′) of this work and 99 compounds XBAY reported by Luo. Based on these data ERed set, through a quantitative regression analysis method and comparison of the factors affecting the ERed, the following results are obtained: (a) Because the phenolic hydroxyl OH can dissociate H+ to form phenolic oxygen anion, the change regularity of ERed of compounds 4-OHBAY and XBAOH-4′ is somewhat different from that of ERed of XBAY compounds without hydroxyl OH. That is, hydroxyl OH has an additional effect on the ERed, which decreases the ERed value. (b) The additional effects of 4-OH on the ERed is different from that of 4′-OH. The effect of hydroxyl OH attached to the aldehyde aromatic ring on the ERed is more than that of OH attached to the amine aromatic ring.
Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage
Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai
, p. 8389 - 8394 (2019/10/16)
C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.
