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PubMed1989

Structure of antischistosome compounds. V 1,6-Hexanediylbis(triphenylphosphonium) dibromide.

C42H42P2(2+).2Br-, Mr = 768.6, triclinic, P1, a = 13.328 (2), b = 23.110 (3), c = 9.417 (1) A, alpha = 90.75 (1), beta = 109.62 (1), gamma = 91.23 (1) degrees, V = 2730.86 A3, Z = 3, Dx = 1.402 g cm3, graphite-monochromatized Cu K alpha radiation, lambda = 1.5418 A, mu = 52.0 cm-1, F(000) = 1182, T = 292 K. Final R = 0.051 for 5225 reflections with I greater than 3 sigma (I). Structure solved by Patterson methods and delta F syntheses. One molecule is located at the center of symmetry of the unit cell. The hexane moieties of all three molecules are in the trans extended conformation. However, one of the P-C-C-C torsion angles in the complete molecule in the asymmetric unit is 118.4 (6) degrees, the corresponding P-C-C-C torsion angle about the other P atom being 178.7 (5) degrees. This creates a conformational asymmetry in an otherwise symmetric molecule. This conformation permits the formation of a nearly square, planar, noncovalent interaction involving this P atom with one of the Br- ions and a symmetry-related Br--P interaction. The remaining P atoms and Br- ions are noncovalently linked to this square, approximately along the alpha axis. This noncovalent network is nearly parallel to the [011] plane, but does not extend beyond the [020] and [020] planes. The half-molecule in the asymmetric unit is approximately 45 degrees to the whole molecule, with two of its phenyl rings directed toward and perpendicular to one of the phenyl rings of the asymmetric triphenylphosphonium group of the whole molecule.(ABSTRACT TRUNCATED AT 250 WORDS)

Crystallization↗
PubMed2004

Radiation damage in coronene, rubrene and p-terphenyl, measured for incident electrons of kinetic energy between 100 and 200 kev.

We have measured the sensitivity of three highly conjugated organic compounds to electron irradiation. Using a 200 keV TEM, loss of crystallinity was determined from quantitative electron-diffraction measurements. Degradation of the molecular ring structure was monitored from fading of the 6 eV pi-excitation peak in the energy-loss spectrum. Measurements at incident energies between 30 keV and 100 eV were made using a scanning electron microscope (SEM), by recording gradual decay of the cathodoluminescence (CL) signal. Expressed in Grays, the energy dose required for CL decay in coronene is a factor of 30 lower than for destruction of crystallinity and a factor of 300 lower than for destruction of the molecular structure. Below 1 keV, the CL-decay cross section shows no evidence of a threshold effect, indicating that the damage involved is caused by valence-electron (rather than K-shell) excitation. Therefore even relatively radiation-resistant organic materials may undergo some form of damage when examined in a low-energy electron microscope or a low-voltage SEM.

Dose-Response Relationship, Radiation↗
PubMed1996

Thermomechanical investigation of poly(methylmethacrylate) containing an organobismuth radiopacifying additive.

Previously we demonstrated the feasibility of using up to 24% triphenylbismuth (TPB) as a radiopaque, monomer-miscible additive for dental acrylic resins. In this study we examined the influence of TPB on thermomechanical properties of a representative polymethylmethacrylate (PMMA) ambient-cured resin used for temporary dental crowns and bridges. TPB (0%, 5%, 15% or 30% w/w) was dissolved in the monomer component, added to the powder component, and allowed to cure in rectangular molds. After 1 h they were either stored at 23 degrees C for 23 h, or heated for 5 min at either 40 degrees C or 50 degrees C, and then stored for 23 h. They were then scanned from -10 degrees to 125 degrees C in a dynamic mechanical thermal analyzer using the three-point bending mode of deformation at 1-Hz frequency. The onset to the glass-transition temperature (Tg) is decreased by 13 degrees to 32 degrees C by addition of TPB, while the storage modulus (E') at 25 degrees C is either unchanged or is slightly increased. TPB did not interfere with the curing reaction, and postcure heating at 40 degrees C had no effect on either E' or Tg. However, heating at 50 degrees C generally increased Tg but had very little effect on E' throughout the 0-50 degree C operating temperature range. TPB crystals were observed to have precipitated at TPB levels above 8%. These crystals, dispersed throughout the PMMA, act as reinforcing fillers. This reinforcement can account for the lack of a decrease in E', as would be expected if TPB had a plasticizing effect below Tg. However, even at 5%, a concentration at which all the TPB remains dissolved in the solid polymer, no decrease in E' was observed. This implies that TPB exerts an antiplasticizing effect at temperatures below 50 degrees C, possibly by occupying free volume among the polymer chains. It is concluded that TPB, in amounts adequate to impart diagnostic levels of radiopacity, is unlikely to adversely affect the clinical utility of PMMA-based dental acrylic resins.

Biocompatible Materials↗
PubMed1992

Cytotoxicity evaluation of a new radiopaque resin additive--triphenyl bismuth.

Triphenyl bismuth (Ph3Bi) is a promising new additive for making biomedical resins visible on x-ray images. We evaluated the cytotoxicity of Ph3Bi, both alone and as a component of a denture resin, as an initial step in determining its biocompatibility. These experimental materials were compared with several types of dental materials that are in current clinical use (PMMA denture acrylic resin, two photo-cured sealants, and two glass-ionomer cements). Human embryonic lung fibroblast tissue cultures (WI-38 cells) were exposed to 24-hour aqueous extracts of the materials. Changes in cell growth, cell viability, and the visual appearance of cells were used for the assessment of toxic response. Only a slight degree of cytotoxicity was observed for Ph3Bi, both alone and in combination with self-cured PMMA. All clinical materials showed a higher level of cytotoxicity than did Ph3Bi. The sealants and cements exhibited the most cytotoxicity and PMMA acrylic the least. The cytotoxicity of PMMA was elevated slightly by inclusion of Ph3Bi, probably due to decreased monomer conversion. When stored in water, the already low levels of cytotoxicity of both PMMA and PMMA with added Ph3Bi were reduced even further. From these results, we can predict a high level of safety for Ph3Bi as a radiopaque additive for biomedical resins. Any toxicity associated with Ph3Bi-containing resins can be reduced or avoided by prior extraction. Alternatively, curing conditions can be selected that would drive the polymerization reaction to a higher level of conversion.

Acrylic Resins↗
PubMed1986

Computer-automated prediction of the mutagenicity of benzidine, 4,4"-diaminoterphenyl, 4-dimethylaminoazobenzene and 4-cyanodimethylaniline: comparison with the results of the Second UKEMS Collaborative Study.

There was agreement between the experimental results, obtained in the course of the Second UKEMS Collaborative Study, for the mutagenicity in Salmonella typhimurium of benzidine, 4,4"-diaminoterphenyl, 4-dimethylaminoazobenzene and 4-cyanodimethylaniline and the mutagenicity predicted by CASE (Computer Automated Structure Evaluation), a recently developed artificial intelligence system.

Aniline Compounds↗
PubMed2003

Effect of triphenyl bismuth on glass transition temperature and residual monomer content of acrylic bone cements.

Self-curing acrylic bone cements are widely used in the fixation of prosthetic implants in orthopaedic surgery. Commercial bone cements are rendered radiopaque by the addition of heavy metal salts of barium and zirconia. The addition of barium sulphate adversely affects the mechanical strength and fracture toughness of bone cement and despite the fact that it has low solubility in water; its slow release and subsequent toxicity have caused concern. In an earlier study triphenyl bismuth (TPB) was found to be a viable alternative as a radiopaque agent in acrylic bone cements, which provided enhanced homogeneity. In this study we report the effect of the inclusion of TPB on the thermal properties of PMMA-based bone cements using both conventional DSC and Modulated Temperature DSC. Furthermore, analysis of the residual monomer contents is reported analysed by NMR spectroscopy in order to ascertain the influence of TPB on the polymerisation reaction. The glass transition temperature (Tg) determined by DSC showed that the values decreased with the addition of increasing amounts of TPB through both blending and dissolution methods; however, the method of incorporating TPB did not influence Tg. The magnitude of reduction was dependent of the amount of TPB and was greatest in the case of highest concentration of TPB used. A TPB melting peak was observed in the 25 wt% TPBBC, suggesting a limit to the solubility of TPB. The residual monomer analysis showed that at 10 and 15% by weight of TPB in the cement caused no significant changes in the residual monomer content but 25 wt% of TPB exhibited a significantly higher residual monomer content.

Calorimetry, Differential Scanning↗