For the first time, herein, we report the synthetic part of the truxene-centred mono-, di- and tri-substituted dipyromethanes (DPMs) in good yields (60-80%) along with their preliminary photophysical (absorption, emission and time resolved fluorescence lifetime) properties. The condensation reaction for assembling the required DPMs were catalyzed with trifluoroacetic acid (TFA) at 0 °C to room temperature (rt), and the stable dipyrromethanes were purified through silica-gel column chromatography. After successfully synthesizing these easy-to-make yet interesting molecules, they were fully characterized by means of the standard spectroscopic techniques (H NMR, C NMR and HRMS).
View Article and Find Full Text PDFIn recent years, truxenes and related polyaromatic hydrocarbons (PAHs) have engrossed ample interest of the scientific community because of their ease of synthesis, functionalizations, and use as building blocks for the synthesis of fullerene fragments, liquid crystals, larger polyarenes, and -tripod materials. In the present work, we have disclosed an ingenious method for the construction of various indolo-truxene hybrid molecules in good yields (52-90%), by means of the acid-catalyzed cotrimerization, Friedel-Crafts acylation, and Fischer indole synthesis, and fully characterized them through the standard spectroscopic techniques. The photophysical properties of the thus-prepared compounds have also been investigated using steady-state absorption and fluorescence and time-resolved fluorescence spectroscopy techniques.
View Article and Find Full Text PDFAn expeditious green method for the synthesis of diverse valued substituted pyrroles through a Paal-Knorr condensation reaction, using a variety of amines and 2,5-hexanedione/2,5-dimethoxytetrahydrofuran in the presence of a low melting mixture of ,-dimethylurea and -(+)-tartaric acid (which acts as a dual catalyst/solvent system), has fruitfully been revealed. Herein, we have disclosed the applicability of this simple yet effective strategy for the generation of mono- and dipyrroles in good to excellent yields. Moreover, -symmetric tripyrrolo-truxene derivatives have also been assembled by means of cyclotrimerization, Paal-Knorr and Clauson-Kaas reactions as crucial steps.
View Article and Find Full Text PDFDesign, synthesis and properties of polycyclic aromatic hydrocarbons (PAHs) has historically attracted a considerable interdisciplinary interest from both fundamental as well as applied viewpoint on account of their wonderful optoelectronic properties. The scientific interest in two-dimensional star-shaped PAHs particularly in truxene architectures arises because of their high thermal stability, exceptional solubility and ease with which they can be constructed and modified. Therefore, bearing in mind a wide range of applications of truxene and its congeners, herein we reveal three novel distinctly different routes for the generation of -symmetric pyrrole-based truxene architectures by means of cyclotrimerization, ring-closing metathesis (RCM), Clauson-Kaas and Ullmann-type coupling reactions as key steps.
View Article and Find Full Text PDFBeilstein J Org Chem
September 2020
Since the first synthetic report in 2003 by Sakurai et al., sumanene (derived from the Indian 'Hindi as well as Sanskrit word' "Suman", which means "Sunflower"), a beautifully simple yet much effective bowl-shaped -symmetric polycyclic aromatic hydrocarbon having three benzylic positions clipped between three phenyl rings in the triphenylene framework has attracted a tremendous attention of researchers worldwide. Therefore, since its first successful synthesis, a variety of functionalized sumanenes as well as heterosumanenes have been developed because of their unique physiochemical properties.
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