Highly Twisted Aryl‐Anthraquinodimethanes: Synthesis, Characterization, and Fluorescence Sensing of TNT

Abstract

A series of anthraquinodimethane (AQ) derivatives substituted with sterically hindered arene groups, including pyrene, tetraphenylethene (TPE), and anthracene, was successfully synthesized through Suzuki–Miyaura cross‐coupling reactions under optimized conditions. The molecular structures of these aryl‐substituted AQs were determined by single‐crystal X‐ray diffraction (XRD) analysis, while their electrochemical and electronic properties were investigated by cyclic voltammetric (CV), UV/Vis absorption, and fluorescence spectroscopic analyses. Our studies provide an in‐depth understanding of the structure‐property relationships for sterically hindered aryl‐AQ systems. Interesting aggregation‐induced emission (AIE) properties for tetrapyrenyl‐ and tetra(TPE)‐substituted AQs were further disclosed, based on which the applicability of these compounds as highly sensitive fluorescent probes for nitroaromatic explosives such as 2,4,6‐trinitrotoluene (TNT) was demonstrated.

Enhanced TNT vapor sensing through a PMMA-mediated AIPE-active monocyclometalated iridium(iii) complex: a leap towards real-time monitoring

“…24 In the quest to detect nitro-based explosive compounds, various luminescent explosive sensors have been developed, leveraging small molecules, conjugated polymers, self-assembled organic nanomaterials, and metal-organic frameworks. 13,14,[25][26][27][28][29][30][31][32][33][34] These have been evaluated for their utility in both solution and vaporphase sensing, but very few reports for fluorescence-based molecules have been employed to detect TNT vapor. 14,19,25,[34][35][36] Mothika and co-workers reported films of tetraphenylene ethylene-based conjugated microporous polymers (PTPETCz) through an electro-polymerization method using tetra(carbazolylphenyl)ethylene monomer, which can detect TNT vapor even at a very low concentration of 33 ppb.…”