Abstract
The obtainment of new luminophores for molecular sensorics of biosystems is becoming one of the urgent tasks in the field of chemical synthesis. The solution to each practical problem imposes its own limitations in the design of new structures with practically useful properties. The relationship between the structure and spectral properties is still to be unveiled. Three aza-BODIPY complexes with substituents of different natures were studied using time-resolved and steady-state fluorescence and absorption spectroscopy. The solvatochromic properties of aza-BODIPYs were studied with the use of a combined polyparametric approach and analysis by chemoinformatics methods for the first time. It was found that red shift of aza-BODIPY dyes was due to the increase of their structural lability. Predictive and experimental methods showed that the investigated aza-BODIPYs exhibited a positive solvatochromic effect, in contrast to classic BODIPYs (bearing C in the meso-position of the dipyrromethene core), which represents the negative solvatochromic properties. Spectral maxima in the area of the therapeutic window, low and predictable solvatochromism, and the ability to fine-tune the spectral characteristics make the investigated aza-BODIPYs promising scaffolds for the construction of bioengineering devices. Generalizations on the aza-BODIPYs’ design patterns were made in accordance with further bioimaging applications.
Highlights
Received: 7 January 2022Today, clinical diagnostic methods based on fluorescence spectroscopy and molecular sensors are being actively developed
Aza-Boron dipyrrin complexes (BODIPYs) 2 was used as a reference compound, bearing ordinary aromatic substituents
The spectral and photophysical properties of aza-BODIPYs 1–3 were studied in a number of solvents of different natures (Figure 2)
Summary
Received: 7 January 2022Today, clinical diagnostic methods based on fluorescence spectroscopy and molecular sensors are being actively developed. Scientists keep looking for new fluorescent molecules that can act as selective sensors to measure the intracellular and intercellular parameters of biological systems [1]. These compounds could be used for the qualitative and quantitative assessment of the ongoing biochemical processes [2]. Synthetic and biogenic luminophores are actively used as sensors and markers of biological processes and conditions [3,4]. They can be used in the design of biomimetic materials [5–7] or smart materials [8–11], allowing one to explore and adapt their properties for a specific task.
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