Preparation of Langmuir–Blodgett Films from Quinoxalines Exhibiting Aggregation-Induced Emission and Their Acidochromism

Abstract

The development of aggregation-induced emission (AIE)-exhibiting compounds heavily relies on our evolving comprehension of their behavior at interfaces, an understanding that still remains notably limited. In this study, we explored the preparation of two-dimensional (2D) sensing films from 2,3-diphenylquinoxaline-based diazapolyoxa-and polyazamacrocycles displaying AIE via the Langmuir−Blodgett (LB) technique. This systematic investigation highlights the key role of the heteroatom-containing tether of 2,3diphenylquinoxalines in the successful fabrication of Langmuir layers at the air−water interface and the transfer of AIE-emitting supramolecular aggregates onto solid supports. Using both diazapolyoxa-and polyazamacrocycles, we prepared AIE-exhibiting monolayer films containing emissive supramolecular aggregates on silica, mica, and quartz glass and characterized them using ultraviolet−visible (UV−vis) and photoluminescence (PL) spectroscopies, atomic force microscopy (AFM) imaging, and fluorescence microscopy. We also obtained multilayer AIE-emitting films through the LB technique, albeit with increased complexity. Remarkably, by employing the smallest macrocycle N 2 C 3 Q, we successfully prepared LB films suitable for the visual detection of acidic vapors. This sensing material, which contains a much lesser amount of organic dye compared with traditional drop-cast films, can be regenerated and utilized for real-life sample analysis, such as monitoring the presence of ammonia in the air and the freshness of meat.