C3-Symmetric Indole-Based Truxenes: Design, Synthesis, and Photophysical Studies

Abstract

In 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 C₃-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. Moreover, the density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations have been studied to correlate them with the measured photophysical properties of the synthesized indolo-truxene derivatives.