5339-06-0Relevant articles and documents
Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X-ray Molecular Structures of meso-{Tetrakis[4-(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands
Nasri, Soumaya,Zahou, Imen,Turowska-Tyrk, Ilona,Roisnel, Thierry,Loiseau, Fredérique,Saint-Amant, Eric,Nasri, Habib
, p. 5004 - 5019 (2016)
The synthesis of the new meso-porphyrin tetrakis[4-(benzoyloxy)phenyl]porphyrin (H2TPBP), the meso-{tetrakis[4-(benzoyloxy)phenyl]porphyrinato}zinc(II) starting material [Zn(TPBP)] (1), and the 1,4-diazabicyclo[2.2.2]octane (dabco), pyrazine (pyz), 4,4′-bipyridine (4,4′-bpy), 4,4′-diaminodiphenylmethane (4,4′-mda), and 4-cyanopyridine (4-CNpy) coordination compounds with [Zn(TPBP)] (2–7) are described. The preparation of the dabco derivative in chlorobenzene leads to a crystalline monomeric five-coordinate zinc porphyrin species (2), whereas the synthesis in dichloromethane gives a five-coordinate zinc metalloporphyrin dimer (3) in the solid state. The pyrazine derivative crystallizes as a bis-pyrazine six-coordinate zinc metalloporphyrin (4). Complex 5 in the solid state is a dimer with 4,4′-bpy as a bridging ligand, whereas the 4,4′-mda species (6) is a five-coordinated monomeric zinc derivative in the solid state. All of structures of 2–6 possess cavities with different dimensions in which solvent molecules are located. The solution UV/Vis spectra of 2–7 exhibit redshifted Soret bands that indicate that these derivatives are five-coordinate zinc(II) porphyrin complexes in solution. UV/Vis titrations show that the association constants of 2–7 are close to those of known five-coordinate zinc(II) meso-porphyrins. The1H NMR spectra of these species confirm this deduction. The photophysical proprieties of 1–7 are similar to those of related zinc(II) meso-porphyrins. The cyclic voltammograms of the H2TPBP free base and 1–7 present a third one-electron reversible oxidation wave. Single-layer diode devices of the [iridium tin oxide/zinc porphyrin/aluminum] configuration show relatively low turn-on voltages.
Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes
Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou
, p. 3286 - 3295 (2022/03/14)
An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.
Functionalized heterocycle-appended porphyrins: Catalysis matters
Abdulaeva, Inna A.,Birin, Kirill P.,Gorbunova, Yulia G.,Polivanovskaia, Daria A.,Tsivadze, Aslan Yu
, p. 42388 - 42399 (2020/12/09)
The scope and limitations of the condensation of labile 2,3-diaminoporphyrin derivatives with aromatic aldehydes to provide functionalized imidazole- and pyrazine-appended porphyrins were investigated in detail. The presence of an acidic catalyst in the reaction was found to be a tool that allows the reaction path to be switched. The influence of the electronic origin of the substituents in the carbonyl components of the condensation on the yields and selectivity of the reaction was revealed. Metal-promoted cross-coupling transformations were found to be convenient for the further targeted construction of functional derivatives based on the prepared bromo-substituted pyrazinoporphyrins. Overall, these strategies provide a versatile technique for the elaboration of a variety of functionalized heterocycle-appended porphyrins for further application in the development of hybrid materials. This journal is
Anti-Markovnikov hydroazidation of activated olefins via organic photoredox catalysis
Nicewicz, David A.,Onuska, Nicholas P. R.,Rosario Collazo, José L.,Schutzbach-Horton, Megan E.
supporting information, p. 55 - 59 (2019/12/30)
Organic azides serve as synthetically useful surrogates for primary amines, a functional group which is ubiquitous in bioactive and medicinally relevant molecules. Historically, the formal hydroazidation of simple activated olefins and styrenes has proven
