In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives (DTTOs) that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

Despite the variety of functional properties of molecular materials, which make them of interest for a number of technologies, their tendency to form inhomogeneous aggregates in thin films and to self-organize in polymorphs are considered drawbacks for practical applications. Here, we report on the use of polymorphic molecular fluorescent thin films as time temperature integrators, a class of devices that monitor the thermal history of a product. The device is fabricated by patterning the fluorescent model compound thieno(bis)imide-oligothiophene. The fluorescence colour of the pattern changes as a consequence of an irreversible phase variation driven by temperature, and reveals the temperature at which the pattern was exposed. The experimental results are quantitatively analysed in the range 20–200°C and interpreted considering a polymorph recrystallization in the thin film. Noteworthy, the reported method is of general validity and can be extended to every compound featuring irreversible temperature-dependent change of fluorescence.

This work explored polysulfone (PS)-graphene oxide (GO) based porous membranes (PS-GO) as adsorbent of seven selected organic contaminants of emerging concern (EOCs) including pharmaceuticals, personal care products, a dye and a surfactant from water. PS-GO was prepared by phase inversion method starting from a PS and GO (5% w/w mixture). The porous PS-GO membranes showed asymmetric and highly porous micrometer sized pores on membrane top (diameter ≈20 μm) and bottom (diameter ≈ 2-5 μm) surfaces and tens of microns length finger like pores in the section. Nanomechanical mapping reveals patches of a stiffer material with Young modules comprised in the range 15-25 GPa, not present in PS pure membranes that are compatible with the presence of GO flakes on the membrane surfaces. PS-GO was immersed in EOCs spiked tap water and the adsorbance efficiency in time and at different pH evaluated by HPLC analyisis. Ofloxacin (OFLOX), Benzophenone-3 (BP-3), rhodamine b (Rh), DCF and triton X-100 (TRX) were removed with efficiency higher than 90% after 4 hours treatments. Regeneration of PS-GO and reuse possibilities were demonstrated by washing with ethanol. The adsorption efficiency toward were Moreover, PS-GO outperformed a commercial granular activated carbon (GAC) at low contact times and compared well at longer contact time for OFLOX, Rh, BP-3 and TRX suggesting the suitability of the newly introduced material for drinking water treatment.

No abstract

The synthesis of two new thieno(bis)imide (TBI, N) end functionalized oligothiophene semiconductors is reported. In particular, trimer (NT3N) and pentamer (NT5N) have been synthesized and characterized. Two different synthetic approaches for their preparation were tested and compared namely conventional Stille cross coupling and direct arylation reaction via C-H activation. Theoretical calculations, optical and electrochemical characterization allowed us to assess the role of the p-conjugation extent, i.e., of the oligomer size on the optoelectronic properties of these materials. In both TBI ended compounds, due to the strong localization of the LUMO orbital on the TBI unit, the LUMO energy is almost insensitive to the oligomer size, this being crucial for the fine-tailoring of the energy and the distribution of the frontier orbitals. Surprisingly, despite its short size and contrarily to comparable TBI-free analogues, NT3N shows electron charge transport with mobility up to l N = 10 À4 cm 2 V À1 s À1 , while increasing the oligomer size to NT5N promotes ambipolar behavior and electroluminescence properties with mobility up to l N = 0.14 cm 2 V À1 s À1 and to l P = 10 À5 cm 2 V À1 s À1 .