A chemical strategy toward the selective synthesis of unsymmetrical tripyrranes was developed for the building of meso-aryl and -nitromethyl substituted A3B porphyrins.
Phosphonates are important organophosphorus compounds which exhibit versatile properties in organic chemistry, medicinal chemistry, materials and biological applications. Phosphonate groups have appeared in a very few examples of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) compounds that are important florescent dyes in these areas. The deficiency in the area motivated us to investigate how the phosphonate substituent(s) affect the structural, electronic, and optical properties of meso, α, or α, α'-substituted BODIPYs using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. We have identified the suitable method as HSEH1PBE functional in combination with the basis set 6-31 + G** by comparing the theoretical results with the experimental studies. Structural, electronic and optical parameters of a series of designed phosphonate substituted 12 BODIPYs (1-4) have been investigated. The α, and α, α'-vinyl phosphonate substituted BODIPYs (3,4) compared to mesosubstituted BODIPYs (1,2) have both lower HOMO/LUMO electronic energies [(À 5.57)-(À 6.19)/(À 3.16)-(À 3.91)] and lower electronic energy gaps (E gap ) (2.11-2.42). Electrostatic potential analysis was performed for all BODIPYs to characterize their electron distribution and TD-DFT analysis was used for the absorption spectral analysis. The presented theoretical approach can be a practical guide for experimental studies for the design of new BODIPY compounds with desired properties.
Organic conductive polymers have great significance due to their wide range of applications in optoelectronics and material sciences. In this study, pyrrole‐benzothiadiazole/benzoselenadiazole based type green polymers were undertaken computational work to investigate the solubility of polymers. Structural, electronic, and optical properties of eight different polymers were predicted using density functional theory (DFT) and time‐dependent‐DFT at B3LYP/6‐31G level on semi‐empirical PM6‐optimized geometries. It has been shown that the calculation results of synthesized green polymers are in great agreement with the experimental results. Alkylated 4,7‐di(1H‐pyrrol‐2‐yl)benzo‐[c][1,2,5]thiadiazole (PB1) and 4,7‐di(1H‐pyrrol‐2‐yl)benzo[c] [1,2,5]selena diazole (PB7) monomers were studied to investigate the effect of alkyl chains on their electronic and optical properties. Butyl substituted more soluble polymers were shown to have low electronic energy gaps (1.27 and 1.55 eV). Moreover, the electronic energy gap values of the studied polymeric structures are in the appropriate range of technological applications (1.24 and 2.18 eV). The approach utilized in this study can be used to design new semi‐conducting polymers.
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