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A rapid high performance liquid chromatographic (HPLC) method for the analysis of caffeine in plasma and saliva is described. Samples of saliva and plasma were purified using zinc sulphate solution as protein precipitant. The supernatant was injected directly onto the column. The mobile phase consisted of ammonium acetate buffer:acetonitrile:methanol (82:15:3, v/v). Measurements were carried out at 254 nm. Acetanilide was used as the internal standard and analysis was completed in 10 min. No interference from endogenous components or other methylxanthines was observed. The coefficients of variation for within day and between day analysis for both saliva and plasma were less than 7.66%. Samples were collected from 20 volunteers. The correlation coefficient between plasma and saliva caffeine concentrations was found to be 0.98.

Dehydrohelicenes are some of the most attractive chiroptical materials with unique helical chirality. However, to our knowledge, there are no prior reports on their direct construction by asymmetric methods. In this work, sequential synthesis of aza-oxa-dehydro[7]helicenes via the electrochemical oxidative hetero-coupling of 3-hydoxycarbazoles and 2-naphthols followed by dehydrative cyclization and intramolecular C–C bond formation has been realized. In addition, an efficient enantioselective synthesis through chiral vanadium-catalyzed hetero-coupling and electrochemical oxidative transformations afforded heterodehydro[7]helicene without any racemization. The obtained dehydro[7]helicenes showed intense blue-colored circularly polarized luminescence (|glum| ≈ 2.5 × 10−3 at 433 nm). Thermodynamic and kinetic studies of the racemization barrier of heterodehydro[7]helicenes indicated significant chiral stability with ΔG‡> 140 kJ mol−1.