Poly(salphenyleneethynylene)s: A New Class\nof Soluble, Conjugated, Metal-Containing\nPolymers
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Bibliographic record
Abstract
Copper(I) iodide, zinc(II) acetate, nickel(II) acetate, vanadyl acetoacetonate, and 4-bromosalicyaldehyde were obtained from Aldrich.Tetrakis(triphenylphosphine)palladium was obtained from Strem Chemicals, Inc. Deuterated solvents were obtained from Cambridge Isotope Laboratories, Inc. Tetrahydrofuran was distilled from sodium/benzophenone under N 2 .NH i Pr 2 was distilled from NaOH under N 2 .4-iodosalicylaldehyde (5), 1,2-didodecyloxy-4,5diaminobenzene (6), and 1,4-dihexyldecyloxy-2,5-diethynylbenzene (9) were prepared by literature methods. [1][2][3] Equipment.All reactions were carried out under N 2 atmosphere unless otherwise noted.300MHz 1 H NMR spectra and 75.5 MHz 13 C NMR spectra were recorded on a Bruker AV-300 spectrometer.UV-Vis spectra were obtained in THF (ca.5x10 -6 M) on a Varian Cary 5000 UV-vis/near-IR spectrometer using a 1 cm cuvette.Fluorescence spectra were obtained in distilled THF (ca.5x10 -6 M) on a Varian Cary Eclipse fluorimeter using a 1 cm cuvette.Quantum yields were referenced to a solution of anthracene in EtOH ( = 0.30). 4The sample solutions were degassed by bubbling N 2 into the cell for 5 minutes.IR spectra were obtained as KBr discs with a Bomens MB-series spectrometer.Molecular weights were estimated by gel permeation chromatography (GPC) using a Waters liquid chromatograph equipped with a Waters 515 HPLC pump, Waters 717 plus autosampler, Waters Styragel columns (4.6 % 300mm) HR2, HR4 and HR5E and a Waters 2410 differential refractometer (refractive index detector).A flow rate of 0.3 mL/min was used and samples were dissolved in THF (ca. 1 mg/mL) and filtered before injection.Narrow molecular weight polystyrene standards were used for calibration purposes.Electrospray (ESI) mass spectra were obtained at the UBC Microanalytical Services Laboratory on a Micromass LCT time-of-flight (TOF) mass spectrometer equipped with an electrospray ion source.The sample was analyzed in MeOH:CHCl 3 at 1M.Electron Impact (EI) mass spectra and elemental Analyses were performed at the UBC Microanalytical Services laboratory.Melting points were obtained on a Fisher-John's melting point apparatus and are corrected.Wide-angle X-ray scattering analyses were obtained on a Rigaku Rotaflex diffractometer equipped with a copper (Cu K, = 1.54184) rotating anode source.Polymers 3 and4. Polymers 3a,b and4a,b were prepared according to literature procedure. 5he black solids obtained from the preparation of 3a and 4a were only slightly soluble in refluxing THF while the black solids obtained from reactions to form 3b and 4b were insoluble.The orange THF solutions containing 3a and 4a were filtered to remove the insoluble matter and precipitated into MeOH under vigorous stirring to yield an orange solid (7 -15% yield) presumably containing oligomeric product.Due to the insolubility of these materials, we were unable to characterize 3 and 4 with 1 H NMR or GPC. Synthesis ofSynthesis of Ligand 7. A solution of 5 (0.500 g, 2.02 mmol) and 6 (0.464 g, 0.97 mmol) in 10 mL of THF was heated to reflux at 70 C for 24 h.After cooling to room temperature, 10 mL of MeOH were added to the reaction mixture under air.Orange needles were obtained overnight, and were isolated by vacuum filtration.The product was recrystallized from THF/MeOH (1:1) to yield 0.740 g (0.79 mmol) of product 7 (81%).Data for 7. 13 C NMR (75.5 MHz, CDCl 3 ) 160.8, 160.2, 149.5, 141.3, 140.1, 135.0, 121.6, 119.9, 104.5, 79.5, 69.8, 31.9, 29.7, 29.6, 29.4,29.4,29.2, 26.0, 22.7, 14.1 ppm; 1 H NMR (300 MHz, CDCl 3 ) 13.14 (s, 2H, OH), 8.49 (s, 2H, CH=N), 7.65 (d, J=2.3 Hz, 2H, aromatic CH), 7.57 (dd, J=2.3, 8.8 Hz, 2H, aromatic CH), 6.82 (d, J=8.8 Hz, 2H, aromatic CH), 6.76 (s, 2H, aromatic CH), 4.04 (t, J=6.6 Hz, 4H, OCH 2 ), 1.84 (m, 4H, CH 2 ), 1.49 (m, 4H, CH 2 ), 1.25 (m, 32H, CH 2 ), 0.86 (t, J=6.8 Hz, 6H, CH 3 ) ppm; UV-vis (THF): max ()= 405 (7520), 348nm (22600), 261 (27600), 255 nm (33200), 250 (30000), 244 (25000) nm (L mol -1 cm -1 ).EI-MS: m/z = 960
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.356 | 0.004 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it