meso-Aryl substituted free-base tripyrrins: preparation and electrochemically induced protonation/deprotonation reactions. Single crystal X-ray analysis of (2,6-diFPh)2TriPyH

RSC Advances ◽  
2015 ◽  
Vol 5 (117) ◽  
pp. 96769-96776 ◽  
Author(s):  
Ru Feng ◽  
Zhongping Ou ◽  
Zhaoli Xue ◽  
Yuanyuan Fang ◽  
Yang Song ◽  
...  
Keyword(s):  
Single Crystal ◽  
Electrochemical Properties ◽  
Free Base ◽  
Nonaqueous Media ◽  
X Ray

Three meso-substituted free-base tripyrrins were successfully isolated as side-products from the synthesis of triarylcorroles and characterized as to their electrochemical properties in nonaqueous media.

Synthesis, characterization and electrochemistry of bismuth porphyrins: X-ray crystal structure of (OEP)Bi(SO3CF3)

2000 ◽  
Vol 04 (03) ◽  
pp. 261-270 ◽  
Author(s):  
LYDIE MICHAUDET ◽  
DOMINIQUE FASSEUR ◽  
ROGER GUILARD ◽  
ZHONGPING OU ◽  
KARL M. KADISH ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Electrostatic Interactions ◽  
Free Base ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Vis Spectroscopy ◽  
Bismuth Salts ◽  
Porphyrin Macrocycles

The metalation of several free base porphyrins by the bismuth salts Bi(NO3)3 and Bi(SO3CF3)3 in DMF or pyridine is described. The resulting stable Bi(III) porphyrin complexes are characterized by electrochemistry, 1H NMR and UV-vis spectroscopy. The structure of ( OEP ) Bi ( SO 3 CF 3) was also determined by single-crystal X-ray diffraction and shows that ( OEP ) Bi ( SO 3 CF 3) exists as a dimer which is stabilized by electrostatic interactions in which the two [(OEP)Bi]+ cations are linked via oxygen atoms of two symmetrically related [Formula: see text] anions, leading to a heptacoordinated bismuth center. Electrochemical oxidation of ( OEP ) Bi ( SO 3 CF 3) and ( T p TP ) Bi ( SO3CF3 ) shows that only the porphyrin macrocycles are oxidized.

scholarly journals TTFs nonsymmetrically fused with alkylthiophenic moieties

2015 ◽  
Vol 11 ◽  
pp. 628-637 ◽  
Author(s):  
Rafaela A L Silva ◽  
Bruno J C Vieira ◽  
Marta M Andrade ◽  
Isabel C Santos ◽  
Sandra Rabaça ◽  
...  
Keyword(s):  
Cyclic Voltammetry ◽  
Charge Transfer ◽  
Single Crystal ◽  
Electrochemical Properties ◽  
X Ray ◽  
Oxidation Processes ◽  
Ligand Precursors ◽  
A Charge

Two new dithiolene ligand precursors, containing fused TTF and alkyl thiophenic moieties 3,3'-{[2-(5-(tert-butyl)thieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-tbtdt, 1), and 3,3'-{[2-(5-methylthieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-mtdt, 2), were synthesized and characterized. The electrochemical properties of these electronic donors were studied by cyclic voltammetry (CV) in dichloromethane. Both compounds show two quasi-reversible oxidation processes, versus Ag/AgCl, typical of TTF donors at E 1 1/2 = 279 V and E 2 1/2 = 680 V for 1 and E 1 1/2 = 304 V and E 2 1/2 = 716 V in the case of 2. The single-crystal X-ray structure of 1 and of a charge transfer salt of 2, (α-mtdt)[Au(mnt)2] (3), are reported.

meso-Tetraphenylporphyrin-derived oxypyriporphyrin, oxypyrichlorin, and thiomorpholinochlorin, as their Ni(II) complexes

2012 ◽  
Vol 16 (05n06) ◽  
pp. 576-588 ◽  
Author(s):  
Subhadeep Banerjee ◽  
Matthias Zeller ◽  
Christian Brückner
Keyword(s):  
Double Bond ◽  
Single Crystal ◽  
Nucleophilic Addition ◽  
Nickel Complex ◽  
Aldol Condensation ◽  
Trans Configuration ◽  
Free Base ◽  
X Ray ◽  
Methylene Groups ◽  
Lawesson's Reagent

trans-Diolchlorin was prepared by nucleophilic addition of methyl-Grignard bromide to meso-tetraphenyl-2,3-dioxoporphyrin, as its free base or Ni(II) complex. The trans-configuration of the vic-diol functionality was shown by single crystal X-ray diffractometry. The nickel complex of the trans-dimethyldiol proved susceptible to Pb(IV) acetate-induced, oxidative diol cleavage, generating a meso-tetraphenylsecochlorin bismethylketone Ni(II) complex, the first example of this chromophore class. Under Brønsted-basic conditions, this bisketone cyclized via an intramolecular aldol condensation to provide a meso-tetraphenyloxypyriporphyrin. Reduction of this porphyrin analog saturated the double bond in the pyridinone moiety, generating an oxypyrichlorin. Reaction of the meso-tetraphenylsecochlorin bismethylketone Ni(II) complex with Lawesson's reagent induced the formation of a thiomorpholinochlorin substituted with two methylene groups, the first example of any porphyrin analog containing a thiomorpholine moiety.

Influence of β-octabromination on free-base triarylcorroles: Electrochemistry and protonation-deprotonation reactions in nonaqueous media

2017 ◽  
Vol 21 (10) ◽  
pp. 633-645 ◽  
Author(s):  
Yang Song ◽  
Yuanyuan Fang ◽  
Zhongping Ou ◽  
Jan Capar ◽  
Chenyi Wang ◽  
...  
Keyword(s):  
Electrochemical Properties ◽  
Published Data ◽  
Free Base ◽  
Acid Base ◽  
Nonaqueous Media ◽  
Strong Electron ◽  
Ring Distortion ◽  
Base Properties

Electrochemical and acid-base properties of four free-base triarylcorroles were examined in nonaqueous media. These compounds are represented here as (tdcc)H[Formula: see text], (tpfc)H[Formula: see text], (Br[Formula: see text]tdcc)H[Formula: see text] and (Br[Formula: see text]tpfc)H[Formula: see text], where tdcc and tpfc are the trianions of tris(2,6-dichlorophenyl)corrole and tris(pentafluorophenyl)corrole, respectively. Different spectroscopic and electrochemical properties were observed for the [Formula: see text]-brominated corroles as compared to the non-brominated derivatives, due in part to the corrole ring distortion and in part to the strong electron-withdrawing properties of the Br groups. The brominated free-base corroles are easier to deprotonate than the non-brominated corroles in solution, which was confirmed by electrochemistry and spectroelectrochemistry as well as protonation/deprotonation reactions of the compounds with acid or base in PhCN. The electrochemistry of the protonated and deprotonated corroles is presented and comparisons made with previously published data for other protonated and deprotonated free-base corroles under the same solution conditions.

Electrochemical Properties and Regioselectivity of Cyclopalladation of Chiral Ferrocenylimines Deriving from (S)-Ferrocenylethylamine

2013 ◽  
Vol 66 (2) ◽  
pp. 218 ◽  
Author(s):  
Zhigang Yin ◽  
Hengyu Qian ◽  
Quanling Wang ◽  
Huichao Dong ◽  
Shihai Yan ◽  
...  
Keyword(s):  
Single Crystal ◽  
Electrochemical Properties ◽  
Phenyl Ring ◽  
Experimental Results ◽  
Computational Studies ◽  
X Ray ◽  
A Minor ◽  
Good Agreement

Treatment of a cyclopalladated complex derived from chiral ferrocenylimine (η5-C5H5)Fe(η5-C5H4)–CH(CH3)–N=CH–2-C4H3S, (Sc)-1, with PPh3 produced the heteroannular palladacycle (Sc)-3 in which palladation occurred at the unsubstituted cyclopentadiene ring. While for (η5-C5H5)Fe(η5-C5H4)–CH(CH3)–N=CH–C6H5, (Sc)-4, cyclopalladation took place mainly at the phenyl ring; the heteroannular palladacycle (Sc)-6, as a minor product, was also obtained. Single crystal X-ray analysis, electrochemical, and computational studies have been performed, showing good agreement with experimental results.

Synthesis, structure, fluorescence, and electrochemical properties of a binuclear Ag(I) complex with 1,4-bis(benzo[d]oxazol-2-yl)butane as a ligand

2020 ◽  
Vol 75 (4) ◽  
pp. 353-357
Author(s):  
Lixian Xia ◽  
Geng Zhang ◽  
Xinzhao Xia ◽  
Yagang Li ◽  
Jiao Wang ◽  
...  
Keyword(s):  
Solid State ◽  
Ir Spectroscopy ◽  
Oxygen Atom ◽  
Single Crystal ◽  
Electrochemical Properties ◽  
Elemental Analysis ◽  
Cyclic Voltammograms ◽  
X Ray Diffraction ◽  
Coordination Environment ◽  
X Ray

AbstractReaction of 1,4-bis(benzo[d]oxazol-2-yl)butane (BBO) with [Ag(CH3CN)4(ClO4)] afforded a new binuclear silver(I) complex, with composition [Ag2(BBO)2(ClO4)2], characterized by elemental analysis, UV/Vis and IR spectroscopy, and single-crystal X-ray diffraction. The results show that the Ag(I) complex consists of a centrosymmetric dimetallacyclic structure assembled from two Ag(I) atoms and two bridging BBO ligands. The coordination environment of silver(I) complex can be described as distorted trigonal planar, with one oxygen atom from a perchlorate anion and two nitrogen atoms from two BBO ligands. The luminescence properties of the ligand and the Ag(I) complex were studied in the solid state. The emission peaks of the Ag(I) complex are attributed to ligand-centered transitions. There is no effect of the complexation except for a partial quenching. The cyclic voltammograms of the Ag(I) complex indicated an irreversible Ag+/Ag couple.

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