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Relevant academic research and scientific papers

Donor-acceptor architectures of tetraphenylethene linked aza-BODIPYs: Synthesis, crystal structure, energy transfer and computational studies

This work is focused on the design and synthesis of donor-acceptor pairs comprising of aza-BODIPY and tetraphenylethene (TPE) fluorogens with large pseudo Stokes shifts (386–424 nm). Femtosecond transient absorption spectroscopy, single crystal X-ray technique and TD-DFT studies were used to get more insight about their spectral behavior. As compared to the tetra-phenylaza-BODIPY, the four aza-BODIPYs exhibited 50–90 nm red shifted absoprtion and emission spectra. When the donor-acceptor architectures were excited at 300 nm, the aza-BODIPY unit emitted strong fluorescence in red region. This suggested an intramolecular energy transfer between donor (TPE) and the aza-BODIPY acceptor; with 81–90% energy transfer efficiencies. Femtosecond transient absorption studies also supported energy transfer process in the molecules, with 3.7 ps time constant associated with it. Aggregation studies in THF/n-heptane solution showed hypsochromic shifts in the aggregated form; X-ray packing structures indicated H-type aggregates (slip angle > 54.7°) in the solid state. Scanning electron microscopy (SEM) measurement revealed 200–700 nm size sphere shaped structures in the aggregated forms.

Poly-halogenated aza-bodipy dyes with improved solubility as a versatile synthetic platform for the design of photonic materials

The optimization of the solubility in organic solvents of halogenated aza-dipyrromethenes was achieved by substitution of the upper phenyl moieties by branched long alkoxy chains (1f) or by using an OMe-OHex-OMe pattern (1h). These results allowed us to prepare original tetra-halogenated aza-dipyrromethenes that were used as a synthetic platform to access highly functionalized aza-bodipy dyes for various potential applications including PDT, imaging, or nonlinear optics. This journal is

The effect of heavy atom to two photon absorption properties and intersystem crossing mechanism in aza-boron-dipyrromethene compounds

Abstract New aza-boron-dipyrromethene compounds containing bromine atoms at various positions were designed and synthesized to enhance the triplet state population and two photon absorption properties for applications such as two-photon photodynamic therapy, triplet-triplet annihilation up-conversion. Steady state fluorescence and ultrafast pump probe spectroscopy techniques revealed that only 2, 6 positions of aza-boron-dipyrromethene core contribute to triplet state population significantly. Density function theory calculations showed that when bromine atoms introduced to 2, 6 position of aza-boron-dipyrromethene core, singlet and triplet energy levels get closer therefore probability of intersystem crossing increases. Z-scan experiments at 800 nm wavelengths revealed considerably large (610 GM) two photon absorption cross section value with respect to literature for compounds showing intersystem crossing mechanism. The efficient intersystem crossing and enhanced two-photon absorption properties make the investigated aza-boron-dipyrromethene compounds good candidates for two-photon photodynamic therapy application.

The synthesis and structures of arene-substituted azadipyrromethenes

We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via the well-established chalcone synthetic method. The stability and yields of these azadipyrromethenes is highly dependent on the nature of the arene substituent, with the bis-pyridine systems exhibiting the highest degree of instability. The structures of several of the compounds and their BF2 adducts are presented; intramolecular hydrogen bonding is observed in the free base ADPMs. We also present a study into the absorption and emission properties of the ADPMs and their BF2 adducts and observe that they are also highly dependent on the identity of the substituents.

Near-infrared nitrofluorene substitued aza-Boron-dipyrromethenes dyes

The synthesis, spectroscopic properties, and TD-DFT calculations of new aza-Boron-dipyromethene dyes featuring pendant nitrofluorenylethynyl substituents are described. This functionalization allows for moving the luminescence in the NIR, conserving a good quantum yield efficiency.