Auswahl der wissenschaftlichen Literatur zum Thema „BODIPY based zwitterionic molecules“

AbstractThe object of the present study are BODIPY molecules obtained previously by Piskorz et al. (Dyes Pigm. 178:108322, 2020) for their antimicrobial activity. Structural analysis of the BODIPY dimers is presented in context of the aggregation influence on the photophysical properties. The thorough investigation of the nature of intermolecular interaction in the representative BODIPY dimers is provided together with the decomposition of the interaction energy into the components of well-defined origin according to SAPT procedure. For the model BODIPY systems the careful examination of the interaction nature for the dimer structure based on experimental crystal study as well as fully optimized is given. The tendencies observed in the model dimers are further on investigated for two pairs of BODIPY systems designed for biomedical application. The analyzed molecules are shown to maximize the mutual interaction by the optimization of the stacking dispersion contacts between the aromatic rings of the molecules, therefore producing stable dimers. The estimation of SAPT0 interaction energy components confirms the dominating dispersion character arising from mutual BODIPY core contacts. The influence of the dimerization process on the photophysical properties of the systems studied theoretically depends to the high extend on the dimerization mode and is significant for parallel and antiparallel dispersion-governed dimers.

A simple meso-pyrrolyl BODIPY-Schiff base conjugate was synthesized by reacting ([Formula: see text]-formylpyrrolyl) BODIPY with 2-aminophenol in ethanol at reflux followed by recrystallization from CH2Cl2/petroleum ether, affording the conjugate in 72% yield. The conjugate was thoroughly characterized by HR-MS, 1D and 2D NMR and X-ray crystallographic techniques. The X-ray structure of the meso-pyrrolyl BODIPY-Schiff base conjugate revealed that the meso-pyrrole and the phenyl substituents were deviated by an angle of [Formula: see text] and [Formula: see text], respectively, from the plane of the BF2-dipyrrin core. The absorption spectrum of the conjugate was similar to the ([Formula: see text]-formylpyrrolyl) BODIPY with a strong absorption band at 508 nm, whereas the fluorescence of the ([Formula: see text]-formylpyrrolyl) BODIPY was completely quenched in the BODIPY-Schiff base conjugate. Furthermore, cation sensing studies revealed that the conjugate has a specific sensing ability for the Cu(II) ion even in the presence of the other metal ions, as verified by the visual, absorption and mass spectral studies. The DFT optimized structure revealed that the Cu(II) ion was bound to pyrrolic nitrogen, imine nitrogen, phenolic oxygen and two water molecules in a distorted square pyramidal fashion. TD-DFT studies accounted well for the absorption spectra of the BODIPY-Schiff base conjugate and its Cu[Formula: see text] bound complex.

Purpose The purpose of this study is to develop a non-enzymatic based glucose-sensing platform composed of Bodipy-BBV dual system which can be monitored by a photodetector under the blue LED excitation. Design/methodology/approach The sensor has been developed from a dual system including a fluorescent dye, an aldehyde derivative of boron dipyrromethene (Bodipy) and a quencher, orto-boronic acid linked viologen (o-BBV) where their combination resulted in a ratiometric fluorescence quenching in ethanol: PBS (1:1, pH:7.4) solution under UV light excitation. By glucose addition, o-BBV has been released from the Bodipy and binded to cis-diol groups of glucose, thereby fluorescence emission of Bodipy has been regained. Furthermore, a setup consisting of a light emitting diode (LED) and a photodiode (PD) was used to prove electrical detection of glucose without the need for expensive and bulky optical equipment, enabling the development of a miniaturized and low-cost glucose-sensing platform. Findings The fluorescence intensity of the Bodipy derivative in the solution (2 × 10−6 M) was diminished by 93% in the presence of o-BBV solution (5 × 10−3 M). Upon the glucose addition, 81% of the Bodipy fluorescence intensity has been recovered after introduction of 30 mM of glucose, where the ratio of o-BBV/Bodipy was 35:1. A linear response between 10 and 30 mM glucose concentration was obtained, which covers the biologically significant range. A high correlation between the photodiode current and Bodipy fluorescence intensity was achieved. Originality/value Even though Bodipy molecules are known with their superior optical properties and applied to the fluorescence-based detection of glucose, to the best of the authors’ knowledge, no work has been reported on Bodipy-BBV dual system to detect glucose molecules as a non-enzymatic based method. This design enables the dye and the quencher to independently coexist in the solution, allowing for tuning of their individual concentrations to optimize the glucose sensitivity. Furthermore, an electrical light detection scheme consisting of a LED and a photodiode has been implemented to eliminate the bulky optical equipment from the measurement setup and further this work for the development of a compact and inexpensive sensor. The results presented here demonstrate the feasibility of this system for the development of a novel glucose sensor.