Tuning supramolecular aurophilic structures: the effect of counterion, positive charge and solvent

Aguiló, Elisabet; Gavara, Raquel; Baucells, Clara; Guitart, Marta; Lima, João Carlos; Llorca, Jordi; Rodrı̀guez, Laura

doi:10.1039/c6dt00865h

Cited by 32 publications

(43 citation statements)

References 64 publications

(94 reference statements)

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“…All the synthesized complexes gave satisfactory elemental analysis and were characterized by 1 H and 31 P NMR and IR spectroscopy as well as by ESI‐MS(+) spectrometry. The 31 P{ 1 H} NMR spectra display in all cases a single resonance, which is around 50 ppm downfield from the resonance of the corresponding free phosphine . Only one peak was recorded for the diphosphine derivatives 7 – 10 , in agreement with the formation of symmetrical dinuclear complexes (see the Supporting Information).…”

Section: Resultssupporting

confidence: 53%

The Important Role of the Nuclearity, Rigidity, and Solubility of Phosphane Ligands in the Biological Activity of Gold(I) Complexes

Svahn

Moro

Roma‐Rodrigues

et al. 2018

Chemistry A European J

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A series of 4-ethynylaniline gold(I) complexes containing monophosphane (1,3,5-triaza-7-phosphaadamantane (pta; 2), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (3), and PR , with R=naphthyl (4), phenyl (5), and ethyl (6)) and diphosphane (bis(diphenylphosphino)acetylene (dppa; 7), trans-1,2-bis(diphenylphosphino)ethene (dppet; 8), 1,2-bis(diphenylphosphino)ethane (dppe; 9), and 1,3-bis(diphenylphosphino)propane (dppp; 10)) ligands have been synthesized and their efficiency against tumor cells evaluated. The cytotoxicity of complexes 2-10 was evaluated in human colorectal (HCT116) and ovarian (A2780) carcinoma as well as in normal human fibroblasts. All the complexes showed a higher antiproliferative effect in A2780 cells, with the cytotoxicity decreasing in the following order 5>6=9=10>8>2>4>7>3. Complex 4 stands out for its very high selectivity towards ovarian carcinoma cells (IC =2.3 μm) compared with colorectal carcinoma and normal human fibroblasts (IC >100 μm), which makes this complex very attractive for ovarian cancer therapy. Its cytotoxicity in these cells correlates with the induction of the apoptotic process and an increase of intracellular reactive oxygen species (ROS). The effects of the nuclearity, rigidity, and solubility of these complexes on their biological activity were also analyzed. X-ray crystal structure determination allowed the identification of short N-H⋅⋅⋅π contacts as the main driving forces for the three-dimensional packing in these molecules.

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Section: Resultssupporting

confidence: 53%

The Important Role of the Nuclearity, Rigidity, and Solubility of Phosphane Ligands in the Biological Activity of Gold(I) Complexes

Svahn

Moro

Roma‐Rodrigues

et al. 2018

Chemistry A European J

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“…75 The latter transitions have been found in related complexes recently reported by us. [76][77][78] The vibronic structured bands are broad and not completely defined even at low concentrations, which are assigned to excitonic splitting where Au⋯Au and π-π intramolecular stacking interactions are present between the arms of the dissolved complexes, as observed in previous studies carried out by our group. 39 The extinction coefficients at the maximum of the absorption band increase with the number of chromophores present in the molecules.…”

Section: Photophysical Characterizationmentioning

confidence: 62%

Polypyridyl-functionalizated alkynyl gold(i) metallaligands supported by tri- and tetradentate phosphanes

et al. 2017

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A series of alkynyl gold(I) tri and tetratopic metallaligands of the type [Au 3 (CuC-R) 3 (μ 3 -triphosphane)] (R = 2,2'-bipyridin-5-yl or C 10 H 7 N 2 , 2,2':6',2''-terpyridin-4-yl or C 15 H 10 N 3 ; triphosphane = 1,1,1-tris(diphenylphosphanyl)ethane or triphos, 1,3,5-tris(diphenylphosphanyl)benzene or triphosph) and [Au 4 (CuC-R) 4 (μ 4 -tetraphosphane)] (R = C 10 H 7 N 2 , C 15 H 10 N 3 ; tetraphosphane = tetrakis(diphenylphosphanylmethyl)methane or tetraphos, 1,2,3,5-tetrakis(diphenylphosphanyl)benzene or tpbz, tetrakis(diphenylphosphaneylmethyl)-1,2-ethylenediamine or dppeda) were obtained in moderate to good yields. All complexes could be prepared by a reaction between the alkynyl gold(I) polymeric species [Au(CuC-R)] n and the appropriate polyphosphane. An alternative strategy that required the previous synthesis of the appropriate acetylacetonate precursors [Au n (acac) n (μ n -polyphosphane)] ("acac method") was assayed, nevertheless only the polyacac derivatives The photophysical properties of the synthesized compounds were carefully studied and used as a probe of their possible use as multidentate ligands for Cu(I) and Zn(II). The UV-Vis speciation studies of the complexation reactions were conducted via metal titration and, in most cases the dangling units of the ligand were found to behave in a fairy independent manner. While in the case of Cu(I) multiple equilibria exist in solution a single complex is detected for Zn(II) under the conditions studied.

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“…These kind of interactions have been observed to be responsible for the formation of micro-and nano-sized supramolecular assemblies. [6][7][8][9][10][11] The formation of large aggregates can induce a quenching effect of the luminescence of the complexes (called Aggregation Induced Quenching, ACQ 12 ) or, on the contrary, an increase on their displayed luminescence (Aggregation Induced Emission, AIE [13][14][15] ).…”

Section: Introductionmentioning

confidence: 99%

Aggregation induced emission of gold(i) complexes in water or water mixtures

et al. 2017

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Gold(i) complexes are an expanding area of investigation due to the possibility of giving rise to supramolecular aggregates with particular morphologies that can be modulated together with their luminescent properties. A detailed study has been carried out for gold(i) complexes that self-assemble in aqueous media (in pure water or in mixtures of water and organic solvents in different proportions). The majority of the examples reported until now were found in mixtures of water and DMSO, acetone, DMF or acetonitrile. The addition of cations to a solution of gold(i) complexes has been observed to show a direct impact on the resulting process of aggregation. The use of perhalogenated ligands together with isocyanide moieties should be highlighted to promote the resulting self-organization. Nevertheless, other ligands like alkynyls or carbenes also promote self-assembly. A careful analysis of the data shows that aurophilic interactions have a key role in the formation of the resulting aggregates and in the enhancement of luminescence (aggregation induced emission, AIE).

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Tuning supramolecular aurophilic structures: the effect of counterion, positive charge and solvent

Cited by 32 publications

References 64 publications

The Important Role of the Nuclearity, Rigidity, and Solubility of Phosphane Ligands in the Biological Activity of Gold(I) Complexes

The Important Role of the Nuclearity, Rigidity, and Solubility of Phosphane Ligands in the Biological Activity of Gold(I) Complexes

Polypyridyl-functionalizated alkynyl gold(i) metallaligands supported by tri- and tetradentate phosphanes

Aggregation induced emission of gold(i) complexes in water or water mixtures

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