Oxidation Products of Cyclic Thiones

Loosmore, Sheena M.; McKinnon, David M.

doi:10.1080/03086647608073326

Cited by 11 publications

(1 citation statement)

References 92 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…28 The hydrogen atom at C2 is then introduced by a substitution/desulfonation process using a proton from the acidic solution as electrophile (see Scheme 2). 29 After evaporation of the solvent a salt metathesis yields the desired products. Either sodium perchlorate or potassium hexafluorophosphate was used to give the N-arylthiazolium perchlorate (ClO 4 ) or hexafluorophosphate (PF 6 ) salts 15−24 (see Scheme 3).…”

Section: ■ Introductionmentioning

confidence: 99%

Photoluminescence of a New Material: Cyclometalated C^∧C* Thiazole-2-ylidene Platinum(II) Complexes

et al. 2016

View full text Add to dashboard Cite

A new class of platinum(II) compounds, the 4,5-dimethyl-3-aryl-thiazole-2-ylidene platinum(II) acetylacetonato complexes, are described. Their efficient phosphorescent emission at room temperature makes them suitable for potential applications in organic light-emitting diodes. A new synthetic pathway that allows the preparation of a broad range of different N-arylthiazole-2-thiones and their subsequent conversion into the corresponding N-arylthiazolium perchlorate and hexafluorophosphate salts has been developed. Not only electron-rich (4-OMe, 4-Me, 3-Me) N-arylthiazoles but also electron-deficient ligands with a cyano or an ester group could be synthesized. From commercially available anilines N-arylthiazolium perchlorate and hexafluorophosphate salts were synthesized via ring-closure of in situ generated N-aryldithiocarbamate salts followed by a sulfur-oxidation/-substitution protocol to the air-stable carbene precursors. All reactions were performed in multigram scale in good yields. The synthesis of the corresponding platinum(II) complexes involves generating the corresponding N-arylthiazole-silver(I)-carbene complexes, transmetalation to platinum, cyclometalation, and reaction with acetylacetonate (acac). Solid-state structures of two N-arylthiazole-2-thiones, one N-arylthiazolium salt, and three N-arylthiazole-2-ylidene-platinum(II) complexes complement the analytic characterization including 195Pt NMR. The unsubstituted complex 4,5-dimethyl-3-phenylthiazole-2-ylidene-platinum(II)-acac was additionally characterized by 2D-NMR techniques (COSY, HSQC, HMBC, NOESY). Photoluminescence measurements were performed in amorphous poly(methyl methacrylate) films and revealed bluish-green emission maxima (∼500 nm) independent of the electronic structure of the thiazoles, whereas the variation of the substitution pattern at the cyclometalating aryl system led to excellent quantum efficiencies and decay lifetimes of 8.1–21.4 μs.

show abstract

Section: ■ Introductionmentioning

confidence: 99%