26334-85-0Relevant academic research and scientific papers
Effect of axial ligands and macrocyclic structure on redox potentials and electron-transfer mechanisms of Sn(IV) porphyrins
Ou, Zhongping,Wenbo,Zhu, Weihua,Thordarson, Pall,Sintic, Paul J.,Crossley, Maxwell J.,Kadish, Karl M.
, p. 10840 - 10849 (2007)
The electrochemical properties of dichloro- and dihydroxo-Sn(IV) porphyrins with three different macrocycles were examined in CH2Cl2 containing 0.1 or 0.2 M tetra-n-butylammonium perchlorate as supporting electrolyte. The investigated compounds are represented as (TPP)SnX2, (P)Sn(X)2, and (PQ)Sn(X)2, where TPP = 5,10,15,20-tetraphenylporphyrin, P = 5,10,15,20-tetrakis(3,5-di-tert- butylphenyl)porphyrin, PQ = 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl) quinoxalino[2,3-b′]porphyrin, and X = Cl or OH. Each porphyrin can be electroreduced in two one-electron-transfer steps with the half-wave potentials and stability of the eletroreduced compounds being dependent upon the type of coordinated axial ligand and specific macrocyclic structure. All reductions of (TPP)Sn(OH)2, (P)Sn(OH)2, and (PQ)Sn(OH)2 are reversible under the given experimental conditions and lead to the expected porphyrin π-anion radicals and dianions, which were characterized by thin-layer UV-vis spectroelectrochemistry. This contrasts with what occurs upon the reduction of (PQ)SnCl2, which undergoes a chemical reaction with trace H2O in solution, leading to the formation of (PQ)Sn(OH) 2 as well as to a protonated form of the quinoxalinoporphyrin, (PQH)Sn(OH)2, under the application of an applied potential. A protonation of the Q group breaks the conjugation between the fused quinoxaline unit and the porphyrin macrocycle, thus effectively giving a compound whose reduction properties resemble that of the metalloporphyrin in the absence of the fused ring. The electrooxidation of each neutral Sn(IV) porphyrin was also investigated, and the effect of axial ligand and fused quinoxaline ring on the redox potentials and products of electron transfer are discussed.
Redistribution reaction on a six-fold coordinated Sn(IV) atom and reactions towards axially unsymmetric substituted Sn(IV) porphyrins
Demitri, Nicola,Fischer, Roland,Gr?ssl, Doris,Stadlbauer, Stefan,Uhlig, Frank
, (2020)
Investigations of the Kocheshkov redistribution reaction were performed on the six fold coordinated tin(IV) atom using the axially coordinated Sn(IV) meso-tetra-phenylporphyrin system with axially trans di-chloro and trans di-acetylido substituted derivatives. The immobile four dentate porphyrin ligand enables the detailed investigation of these typically complex reaction systems on higher coordinated tin(IV) species. The thermally activated reaction displays an equilibrium. Further on, a series of axial unsymmetrically substituted Sn(IV) porphyrins are selectively synthesized and described.
Photophysical properties of Sn (IV)tetraphenylporphyrin-pyrene dyad with a β-vinyl linker
Reeta, P. Silviya,Khetubol, Adis,Jella, Tejaswi,Chukharev, Vladimir,Abou-Chahine, Fawzi,Tkachenko, Nikolai V.,Giribabu,Lemmetyinen, Helge
, p. 288 - 300 (2015)
A Sn(IV)tetraphenylporphyrin (T) has been functionalized with a β-vinyl pyrene (P) and the photophysical properties of the formed dyad (T-P) with its corresponding precursors were studied in three solvents with different polarities using steady-state and
Photocatalytic Properties and Mechanistic Insights into Visible Light-Promoted Aerobic Oxidation of Sulfides to Sulfoxides via Tin Porphyrin-Based Porous Aromatic Frameworks
Jiang, Jun,Luo, Rongchang,Zhou, Xiantai,Chen, Yaju,Ji, Hongbing
supporting information, p. 4402 - 4411 (2018/10/15)
Using concepts of biomimetic catalysis, a kind of tin porphyrin-based porous aromatic framework (SnPor@ PAF) with broad and strong optical absorption in the visible light region was successfully synthesized and subsequently used in the aerobic oxidation of sulfides to sulfoxides under ambient conditions and visible light irradiation, in which exhibited enzyme-like features of high efficiency and high selectivity. More interestingly, heterogeneous SnPor@PAF was naturally regarded as an intriguing and versatile photosensitizer for photocatalytic transformation and could be reused several times because of its robust and rigid porphyrin framework. As expected, their π-conjugated structure characteristic in the molecular skeleton might facilitate the activation of molecular oxygen under mild reaction conditions and promoted the production of reactive oxygen species (singlet oxygen (1O2) and superoxide radical anion (O2.?)), which would involve energy transfer and/or electron transfer process. Experimental investigations including emission quenching experiment, oxygen-isotope labelling, typical inhibition experiments, classical fluorescence probe study, photo-oxidation of α-terpinene and in situ electron spin resonance, could provide a mechanistic insight into the photocatalytic reactions. (Figure presented.).
A [2]catenane and pretzelane based on Sn-porphyrin and crown ether
Han, Min,Zhang, Heng-Yi,Yang, Li-Xu,Ding, Zhi-Jun,Zhuang, Rui-Jie,Liu, Yu
scheme or table, p. 7271 - 7277 (2012/01/13)
A [2]catenane and a pretzelane that consist of one aromatic dialkylammonium spacer, one dibenzo-24-crown-8 (DB24C8) unit, and one Sn-porphyrin dihydroxide component were synthesized. In the [2]catenane, dibenzo-24-crown-8 and the Sn-porphyrin dihydroxide
Supramolecular bidentate phosphorus ligands based on bis-zinc(ii) and bis-tin(iv) porphyrin building blocks
Slagt, Vincent F.,Van Leeuwen, Piet W. N. M.,Reek, Joost N. H.
, p. 2302 - 2310 (2007/10/03)
Selective metal-ligand interactions have been used to prepare supramolecular bidentate ligands by mixing monodentate ligands with a suitable template. For these assemblies pyridine phosphorus ligands and a zinc(II) porphyrin dimer were used. In the rhodium-catalysed hydroformylation of 1-octene and styrene improved selectivities have been obtained for some of the assembled bidentate ligand systems. In the palladium catalysed asymmetric allylic alkylation similar effects were observed; the enantioselectivity increased by using a bisporphyrin template. The preparation of supramolecular catalyst systems was also explored using tin-oxygen interactions. Dihydroxotin(iv) porphyrin and carboxylic phosphorus ligands assemble into supramolecular ligands and the phosphorus donor atom coordinates to transition metals. The stronger oxygen-tin bond, compared to pyridine-zinc does not result in a better performance of the catalyst. The Royal Society of Chemistry.
Efficient formation of lipophilic dihydroxotin(IV) porphyrins and bis-porphyrins
Crossley,Thordarson,Wu
, p. 2294 - 2302 (2007/10/03)
Treatment of dichloro- and dicarboxylato-tin(IV) porphyrins with K2CO3 in THF-H2O (4 : 1) is a mild and highly efficient method for formation of dihydroxotin(IV) porphyrins; unlike other reported procedures, this method is
