Hypervalent triphenyl and diphenyl tin coordination compounds derived from 2-(1H-benzimidazol-2-yl)phenol

Esparza‐Ruiz, Adriana; Peña-Hueso, Adrián; Ramos-Garcı́a, Iris; Vásquez-Badillo, Aurora; Flores‐Parra, Angelina; Contreras, Rosalinda

doi:10.1016/j.jorganchem.2008.10.037

Cited by 8 publications

(1 citation statement)

References 26 publications

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“…[55] Interestingly, the large upfield shifts in the 119 Sn NMR spectra were observed in DMSO-d 6 (À 467.3 ppm for TAz-H, À 471.1 ppm for TAz-F, À 465.0 ppm for TAz-OBu and À 475.9 ppm for TAz-CF3, Figure S2), strongly suggesting that the DMSO coordination should proceed at the tin atom followed by the formation of the six coordinated state. [56][57][58][59] This result also means that the asymmetric five-and six-coordinated structures can be obtained by selecting the solvent between CDCl 3 and DMSO-d 6 , respectively. Noted that the complexes involving six-coordinated states showed high stability.…”

Section: Nmr Spectramentioning

confidence: 83%

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Gon

Tanaka

Chujo

2021

Chemistry A European J

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The dynamic and reversible changes of coordination numbers between five and six in solution and solid states, based on hypervalent tin(IV)-fused azobenzene (TAz) complexes, are reported. It was found that the TAz complexes showed deep-red emission owing to the hypervalent bond composed of an electron-donating three-center four-electron (3c-4e) bond and an electron-accepting nitrogen-tin (N-Sn) coordination. Furthermore, hypsochromic shifts in optical spectra were observed in Lewis basic solvents because of alteration of the coordination number from five to six. In particular, vapochromic luminescence was induced by attachment of dimethyl sulfoxide (DMSO) vapor to the coordination point at the tin atom accompanied with a crystal-crystal phase transition. Additionally, the color-change mechanism and degree of binding constants were well explained by theoretical calculation. To the best of our knowledge, this is the first example of vapochromic luminescence by using stable and variable coordination numbers of hypervalent bonds.

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Section: Nmr Spectramentioning

confidence: 83%

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Gon

Tanaka

Chujo

2021

Chemistry A European J

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Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

et al. 2016

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The ferrocenyl‐containing 3,5‐di‐tert‐butylcatechol Fc‐L‐CatH2 (2) was synthesized by the condensation of the precursor 6‐(hydrazonomethyl)‐3,5‐di‐tert‐butylcatechol 6‐(H2N–N=CH)CatH2 (1) with ferrocenecarboxaldehyde (L = –CH=N–N=CH–, Cat = 3,5‐di‐tert‐butylcatecholate, Fc = ferrocene). The exchange reaction between catechol 2 and Ph3SbBr2 in the presence of a base (Et3N) in toluene leads to the formation of the triphenylantimony(V) catecholate (Fc‐L‐Cat)SbPh3 (3) as the main product and the ionic bromotriphenylantimony(V) catecholate (Fc‐LH‐Cat)SbPh3Br (4) containing a hydraziniumylidene cation (LH = –CH=NH+–N=CH–) as the byproduct. The change of toluene to tetrahydrofuran (THF) results in the formation of 4 as the main product in nearly quantitative yield. The exchange reactions of catechol 2 with Ph2SnCl2 and SnCl4 give anionic catecholate complexes bridged with hydraziniumylidene cations even in the presence of excess base. Complexes (Fc‐LH‐Cat)SnPh2Cl (5), (Fc‐LH‐Cat)2SnPh2 (6), and (Fc‐LH‐Cat)2SnCl2 (7) were synthesized. The compounds obtained were characterized by IR spectroscopy, 1H and 13C NMR spectroscopy, elemental analysis, and cyclic voltammetry. The molecular structures of crystals of 5–7 were determined by X‐ray diffraction analysis. The formation of catecholates 4–7 with hydraziniumylidene cations is caused by intramolecular hydrogen bonding between the hydroxy and imine groups, which leads to proton transfer from the oxygen atom to the nitrogen atom of the hydrazine linker.

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Organometallic Tin Compounds Derived from 2‐Benzimidazole Propionic Acid

Camacho‐Camacho

Esparza‐Ruiz

Peña-Hueso

et al. 2013

Zeitschrift anorg allge chemie

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Reactions of 2‐benzimidazole propionic acid (1) with [Sn(nBu)3]2O and SnPh3OH gave mononuclear organometallic tin esters 2 and 3, respectively, where 1 is coordinated to the tin atom through the carboxylate group. Further reactions of 2 with DMSO and 3 with methanol, ethanol, pyridine, DMSO, THF and water afforded the corresponding tin compounds coordinated by the base 4–10, respectively. X‐ray diffraction analyses of 5, 6 and 10 were obtained. The solid‐state structures showed that the ligand 1 is bound through both oxygen atoms of the carboxylic group with the Lewis base anti to it. Reaction of 1 with di‐n‐butyltin oxide produced a tetranuclear distannoxane (11) by the association of four Sn(nBu)2 groups, two oxygen atoms and four ligands. Four of the oxygen atoms are tricoordinate. The tin atoms are hexacoordinate with distorted octahedral geometries. The macromolecule has in total seven fused rings. Five of them are four membered rings arranged in a ladder‐type arrangement and the other two are six membered rings. The aliphatic chains and the benzimidazole groups are perpendicularly oriented to the polycyclic arrangement giving a sandwich with polar bonds in the middle and covered by the aliphatic and aromatic groups. In all compounds the ligands showed a chiral helicoidal preferred conformation.

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Hypervalent triphenyl and diphenyl tin coordination compounds derived from 2-(1H-benzimidazol-2-yl)phenol

Cited by 8 publications

References 26 publications

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

Organometallic Tin Compounds Derived from 2‐Benzimidazole Propionic Acid

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