A novel macrocyclic organotin carboxylate containing a nona-nuclear long ladder

Xiao, Xiao; Shao, Kui‐Zhan; Ling, Yinghui; Mei, Ze-Min; Zhu, Dongsheng; Xu, Lin

doi:10.1039/c3dt50531f

Cited by 36 publications

(22 citation statements)

References 39 publications

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“…These bands are absent in the spectrum of Sul which is most likely due to the symmetric vibration of the ligated COO − group. High magnitude of Δ ν ( ν as COO − ν s COO) for 1 (286 cm −1 ), 2 (306 cm −1 ) and 3 (287 cm −1 ) as compared to sodium salt of drug (261 cm −1 ) indicates that the carboxylate group acts as a monodentate donor group and hence the possibility of ionic bonding, bridging and chelation can be excluded . However, for 4 and 6 the magnitude of Δ ν is 163 and 217 cm −1 , respectively, which indicates the probability of bidentate mode of coordination of carboxylate group.…”

Section: Resultsmentioning

confidence: 98%

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Kumari

Nath

2017

Applied Organom Chemis

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Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac (Sul), coordinated with carboxylate oxygen, namely C23H25FO3SSn (1), C38H31FO3SSn (2), C32H43FO3SSn (3), C52H42F2O6S2Sn (4), C44H44S2Cl2O6F2Sn2 (5), C48H50F2O6S2Sn (6) and C56H66F2O6S2Sn (7), have been synthesized and characterized using analytical and spectroscopic (IR, 1H NMR, 13C NMR, 119Sn NMR and ESI‐MS) techniques. Optimized geometry and electronic structures of the complexes obtained from density functional theory calculations indicate that complexes 1, 2, 3 and 7 are tetra‐coordinated with monodentate carboxylates, 4 and 6 are hexa‐coordinated with highly distorted octahedral geometry, whereas 5 is penta‐coordinated with distorted trigonal bipyramidal geometry. Probable mode of DNA binding with ligand (Sul) and complexes 1–7 has been revealed via various biophysical techniques (UV–visible spectroscopy, fluorometry and circular dichroism). Intrinsic binding constants (Kb) obtained from UV–visible spectroscopy for Sul and complexes 1–7 are 3.69 × 104, and 7.3 × 103, 1.14 × 104, 1.47 × 104, 1.55 × 104, 1.49 × 104, 2.02 × 104, 1.17 × 104 M−1, respectively. The quenching constants (Ksv) using fluorometric titrations, calculated from competitive binding of ethidium bromide versus Sul/complexes with calf thymus DNA, also correspond to the above results. Circular dichroism spectral patterns of calf thymus DNA with Sul and complexes 1–7 have also been investigated. All the results reveal that the complexes bind with DNA through partial intercalative mode. pBr322 plasmid fragmentation has also been studied using gel electrophoresis, which shows the fragmentation of circular DNA by an increase in nicked form and also by the appearance of linear form with increasing concentration of drug or complexes.

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Section: Resultsmentioning

confidence: 98%

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Kumari

Nath

2017

Applied Organom Chemis

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“…[170,171,172,173], wherein the organotin compounds, especially ubiquitous organotin carboxylates, exhibit a range of effects for chemotherapy, biological, catalytic and industrial applications [174,175,176,177]. Although their properties including diversity of structures for constructing novel compounds, assembly/self-assembly for polymers, and anti-tumor/anti-bacterial have been systematically investigated [178,179,180,181], only a few studies regarding the two-photon absorption properties of the organotin carboxylate derivatives have been reported. Hence, our efforts have been directed towards the search for optimized molecular structures having large 2PA cross-sections.…”

Section: Design Strategies Structure-property Relationships and mentioning

confidence: 99%

Lighting the Way to See Inside Two-Photon Absorption Materials: Structure–Property Relationship and Biological Imaging

et al. 2017

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The application of two-photon absorption (2PA) materials is a classical research field and has recently attracted increasing interest. It has generated a demand for new dyes with high 2PA cross-sections. In this short review, we briefly cover the structure-2PA property relationships of organic fluorophores, organic-inorganic nanohybrids and metal complexes explored by our group. (1) The two-photon absorption cross-section (δ) of organic fluorophores increases with the extent of charge transfer, which is important to optimize the core, donor-acceptor pair, and conjugation-bridge to obtain a large δ value. Among the various cores, triphenylamine appears to be an efficient core. Lengthening of the conjugation with styryl groups in the D-π-D quadrupoles and D-π-A dipoles increased δ over a long wavelength range than when vinylene groups were used. Large values of δ were observed for extended conjugation length and moderate donor-acceptors in the near-IR wavelengths. The δ value of the three-arm octupole is larger than that of the individual arm, if the core has electron accepting groups that allow significant electronic coupling between the arms; (2) Optical functional organic/inorganic hybrid materials usually show high thermal stability and excellent optical activity; therefore the design of functional organic molecules to build functional organic-inorganic hybrids and optimize the 2PA properties are significant. Advances have been made in the design of organic-inorganic nanohybrid materials of different sizes and shapes for 2PA property, which provide useful examples to illustrate the new features of the 2PA response in comparison to the more thoroughly investigated donor-acceptor based organic compounds and inorganic components; (3) Metal complexes are of particular interest for the design of new materials with large 2PA ability. They offer a wide range of metals with different ligands, which can give rise to tunable electronic and 2PA properties. The metal ions, including transition metals and lanthanides, can serve as an important part of the structure to control the intramolecular charge-transfer process that drives the 2PA process. As templates, transition metal ions can assemble simple to more sophisticated ligands in a variety of multipolar arrangements resulting in interesting and tailorable electronic and optical properties, depending on the nature of the metal center and the energetics of the metal-ligand interactions, such as intraligand charge-transfer (ILCT) and metal-ligand charge-transfer (MLCT) processes. Lanthanide complexes are attractive for a number of reasons: (i) their visible emissions are quite long-lived; (ii) their absorption and emission can be tuned with the aid of appropriate photoactive ligands; (iii) the accessible energy-transfer path between the photo-active ligands and the lanthanide ion can facilitate efficient lanthanide-based 2PA properties. Thus, the above materials with excellent 2PA properties should be applied in two-photon applications, especially two-photon fluorescence m...

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“…These compounds produce fascinating and attractive architectures through hydroxo and/or oxo bridges, for example, rings, cages and clusters with variable nuclearity in the form of ladders, drums, butterflies and cubic topologies. In the past, ladder-like Sn clusters have been reported with organotin(IV) Schiff base compounds, [39,40] organotin heterocyclic thiol compounds derived from 2-mercapto-1,3,4-thiadiazole, [41] organotin sulfonates, [42,43] organotin(IV) cyanoximates, [44] tetraorganodistannoxanes, [45] organotin carboxylates [46][47][48][49][50][51] and organotin diimido compounds. [52] In all these clusters, Sn 2 O 2 is the predominant unit, with the simple Sn-O-Sn "chain" relatively less encountered.…”

Section: Introductionmentioning

confidence: 99%

Diverse Molecular Architectures of Si and Sn [4.4.3.0^1,6]Tridecane Cages Derived from a Mannich Base Possessing Semi‐Rigid Unsymmetrical Podands

et al. 2016

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Three novel atrane-like pentacoordinate silicon and hexa-and mixed penta-and hexacoordinate tin compounds containing [4.4.3.0]tridecane cages have been synthesized. In the present work, the bis-phenol amine tetradentate ligand, N,N-bis(2-hydroxy-3,5-dimethylbenzyl)-2-aminoethanol (H 3 L), was treated with phenyltrichlorosilane, butyltrichlorostannane and phenyltrichlorostannane to give the mononuclear pseudosilatrane 1, dinuclear pseudo-stannatrane 2 and tetranuclear pseudo-stannatrane 3, respectively. These compounds were characterized by spectroscopic techniques ( 1 H,

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A novel macrocyclic organotin carboxylate containing a nona-nuclear long ladder

Cited by 36 publications

References 39 publications

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Lighting the Way to See Inside Two-Photon Absorption Materials: Structure–Property Relationship and Biological Imaging

Diverse Molecular Architectures of Si and Sn [4.4.3.0^1,6]Tridecane Cages Derived from a Mannich Base Possessing Semi‐Rigid Unsymmetrical Podands

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A novel macrocyclic organotin carboxylate containing a nona-nuclear long ladder

Cited by 36 publications

References 39 publications

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Lighting the Way to See Inside Two-Photon Absorption Materials: Structure–Property Relationship and Biological Imaging

Diverse Molecular Architectures of Si and Sn [4.4.3.01,6]Tridecane Cages Derived from a Mannich Base Possessing Semi‐Rigid Unsymmetrical Podands

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Diverse Molecular Architectures of Si and Sn [4.4.3.0^1,6]Tridecane Cages Derived from a Mannich Base Possessing Semi‐Rigid Unsymmetrical Podands