A simple and efficient procedure for the synthesis of a new class of selenoesters 4a and 4b was developed. Polarized-light optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction showed that the selenoester 4a with a shorter alkyl chain displayed a wide nematic range (ΔT = 110.7 °C), while 4b with a longer alkyl chain possesses a rich phase polymorphism: Cr → SmI → SmC → N → I mesophase sequence during heating cycle and I → N → SmC → SmI → SmX → Cr transition on cooling. For 4b, a large temperature range (135.7 °C) from crystal to isotropic phase can be observed. In addition, UV-Vis, steady-state fluorescence emission and excitation spectra in solution were also applied in order to characterize their photophysical behaviour. Compounds 4a and 4b are fluorescent in the blue region and present a Stokes shift at around 80 nm and 39 nm in dichloromethane and dioxane, respectively.
1 January 2021 in Bioorganic & Medicinal Chemistry
Coumarins have been used in a wide range of applications, such as dye-sensitised solar cells, laser dyes and optical sensors. In order to further explore the properties of these materials, three new coumarin derivatives were obtained with different terminal arylalkyne linkages to the 6-position of the coumarin core. The synthesised materials were characterised by NMR, absorption and emission spectroscopy, and the liquid crystal properties were investigated through differential scanning calorimetry and polarised optical microscopy. In addition, dye-sensitised solar cells were assembled to evaluate the photoelectrochemical properties of the materials. Only the coumarin with a naphthyl group exhibited stable smectic A and nematic mesophases. All the coumarins were photoemissive in the range 420–461 nm. The adsorption of these dyes on TiO2 was observed by UV–vis spectroscopy; in addition, by incident photon-to-electron conversion efficiency and I–V curves, photocurrent generation was observed.