Poly(salphenyleneethynylene)s: A New Class\nof Soluble, Conjugated, Metal-Containing\nPolymers
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Notice bibliographique
Résumé
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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Prédiction distillée sur la base complète
Imitation des enseignantsNi prévalence calibrée, ni vérité terrain. Validation humaine à venir. Apprise à partir de 10 348 étiquettes directes de Codex et de 10 348 étiquettes directes de Gemma. Le mode candidate est l'union des têtes enseignantes seuillées; le consensus est leur intersection. Ces sorties portent le statut machine_predicted_unvalidated et ne sont ni des étiquettes humaines ni des étiquettes directes de modèles de pointe.
Scores Codex et Gemma par catégorie
| Catégorie | Codex | Gemma |
|---|---|---|
| Métarecherche | 0,000 | 0,000 |
| Méta-épidémiologie (sens strict) | 0,000 | 0,000 |
| Méta-épidémiologie (sens large) | 0,000 | 0,000 |
| Bibliométrie | 0,000 | 0,000 |
| Études des sciences et des technologies | 0,000 | 0,000 |
| Communication savante | 0,000 | 0,000 |
| Science ouverte | 0,000 | 0,000 |
| Intégrité de la recherche | 0,000 | 0,000 |
| Charge utile insuffisante (le modèle a refusé de juger) | 0,356 | 0,004 |
Scores machine (provisoires)
Les deux têtes enseignantes du modèle étudiant, lues sur ce travail. Un score ordonne la base pour la relecture; il n'affirme jamais une catégorie, et le statut de validation accompagne chaque rangée tel quel.
Scores de référence d'un modèle non mature (critères de maturité non atteints, 7 itérations). Un score ordonne; il n'affirme jamais une catégorie.
score_only:v0-immature-baseline · tel quel depuis la passe de notation : score_only signifie que le nombre peut ordonner les travaux, et qu'aucune étiquette de catégorie n'en découle