Spectral Properties and Possibilities of meso-Substituted BODIPY Usage in Sol–Gel Process and Materials

Abstract

Hybrid materials based on organically modified silica with immobilized boron-dipyrrins (BODIPY) dyes were obtained. Spectral characteristics of the dyes were measured during the matrix formation and in obtained materials. It was stated, that immobilization does not affect the character of the absorption and fluorescence spectra of the dye, but due to the effect of fluorescent molecular rotor observed for meso-substituted BODIPY, the fluorescent quantum yields were found to increase during the matrix sealing. Quantum yield increase is linear for all of the investigated matrices except phenyl-substituted one, where the π-π interactions of the dye molecule with matrix could be observed. This effect could be used for fine control of the matrix formation process and leads to increase of the dye emission in the final material for further practical applications. All obtained hybrid materials were found to be stable upon UV light irradiation, hence immobilization enhance the stability of the dye in comparison with the BODIPY in organic solvents.

On the Use of Polymer-Based Composites for the Creation of Optical Sensors: A Review

“…There are many polar substituents that contribute to the formation of dipole interactions with the corresponding substrates. Such matrices include: among the organic ones most popular are oligo-polysaccharides [ 46 , 47 ], cellulose [ 48 , 49 , 50 , 51 ], polymethylmethacrylate (PMMA) [ 52 , 53 , 54 , 55 ], polyvinyl chloride (PVC) [ 11 , 56 ]; among inorganic ones most popular are silica and other polymeric oxides obtained by sol-gel synthesis [ 57 , 58 , 59 , 60 , 61 , 62 ]. On the other hand, the luminophore must have the following groups (one or several): H-, hydroxo-, amino-, nitro-, sulpho-, mercapto- and groups comprising from atoms with an unsplit electron pair and capable of forming a donor-acceptor bond; phenyl and other cyclically conjugated molecules to form π-π stacking.…”

“…For example, using matrices of silica and its organo-modified counterpart, a pH sensor can be produced using the sol-gel method. And depending on the choice of matrix, the nature of the sensor response may vary or not appear at all [ 61 ]. PMMA matrices with BODIPY can be used to produce sensors for polarity reversal of the environment [ 62 ].…”

Photoinduced and Classical Sol-Gel Synthesis: Spectral and Photophysical Behavior of Silica Matrix Doped by Novel Fluorescent Dye Based on Boron Difluoride Complex

“…For this reason, many strategic solves have been found to enhance solid state emission such as substitution in the following at the meso position and also in 2,6-positions and 3,5-positions result in more spaced packing in the solid state, resulting in highly fluorescence in solid materials (powders or films) [ 18 , 20 ]. Thus, studies of BODIPY obtained by means of the sol-gel process are still of continuing interest at present as it retains the properties of luminophores in hybrid materials, and the active ingredient becomes extra resistant to raised temperatures and strong ultraviolet radiation [ 21 ]. Moreover, generally low stokes shifts (<15 nm in most cases) are one of the significant drawbacks in the properties of BODIPY dyes [ 22 ] which causes self-quenching in the solid state [ 8 ].…”

Bodipy Based Fluorescent Materials in Cellulose Matrices: Synthesis, Spectral Properties and Vapochromic Fluorescent Recognition of Alcohols and Acetone

“…Technological applications mostly utilize stabilized functional materials of optically active compounds immobilized in carefully selected polymers, instead of the neat compounds [15,16]. There is a broad variety of papers covering immobilization of BODIPY into matrices of various nature for specific practical applications.…”