Synthesis and Characterization of a Novel Green Cationic Polyfluorene and Its Potential Use as a Fluorescent Membrane Probe

Abstract

In the present work, we have synthesized a novel green-emitter conjugated polyelectrolyte Copoly-{[9,9-bis(6′-N,N,N-trimethylammonium)hexyl]-2,7-(fluorene)-alt-4,7-(2-(phenyl) benzo[d] [1,2,3] triazole)} bromide (HTMA-PFBT) by microwave-assisted Suzuki coupling reaction. Its fluorescent properties have been studied in aqueous media and in presence of model membranes of different composition, in order to explore its ability to be used as a green fluorescent membrane probe. The polyelectrolyte was bound with high affinity to the membrane surface, where it exhibited high fluorescence efficiency and stability. HTMA-PFBT showed lower affinity to zwitterionic membranes as compared to anionic ones, as well as a more external location, near the membrane-aqueous interface. Fluorescence microscopy studies confirmed the interaction of HTMA-PFBT with the model membranes, labelling the lipid bilayer without perturbing its morphology and showing a clear preference towards anionic systems. In addition, the polyelectrolyte was able to label the membrane of bacteria and living mammalian cells, separately. Finally, we explored if the polyelectrolyte can function also as a sensitive probe able of detecting lipid-phase transitions. All these results suggest the potential use of HTMA-PFBT as a green membrane marker for bioimaging and selective recognition of bacteria cell over mammalian ones and as a tool to monitor changes in physical state of lipid membranes.

Physico-Chemically Distinct Nanomaterials Synthesized from Derivates of a Poly(Anhydride) Diversify the Spectrum of Loadable Antibiotics

“…In particular, it is reported that PMVE/MA can be structured as loadable nanoparticles [9] and its derivates poly(methyl vinyl ether-alt-maleic acid) (PMVE/MA-Ac) and poly(methyl vinyl ether-alt-maleic monoethyl ester) (PMVE/MA-Es) as nanofibers [10,11]. In addition, these polymers have shown utility as matrix elements, allowing the combination with other materials to generate novel mixtures of chemical properties in the final nanostructures [11][12][13], such as with homemade fluorescent cationic fluorene-based polyelectrolytes [11,[14][15][16].…”

Fluorene-Based Donor-Acceptor Copolymers Containing Functionalized Benzotriazole Units: Tunable Emission and their Electrical Properties

“…On the other hand, benzotriazole unit is a multitask skeleton which has been used in other areas, for example, as organic waveguides [29], in organogels [30], as semiconductors in OFETs [31], and as fluorescence sensors in biomedicine [32]. Previously in our groups, we have described the use of 4,7dialkynyl-2H-benzo[d]1,2,3-triazole derivatives as semiconductors in OFETs [31].…”

High thermal stability, pH responsive organogels of 2H-benzo[d]1,2,3-triazole derivatives as pharmaceutical crystallization media

“…A convenient functionalization of the benzotriazole moiety has afforded derivatives with application as optical waveguides, 22 organic fieldeffect transistors, 23 and in bioimaging. 24 In this work, we report a series of novel 2H-benzo[d]1,2,3-triazole derivatives that function as LMW organogelators and the application of their gels as drug crystallization media.…”