Trifluoromethyl‐Substituted Perylene Diimides for Rapid and Sensitive Film‐Based Fluorescence Detection of Methamphetamine and Cocaine Hydrochloride

Abstract

Film‐based fluorescence sensors are attractive for rapid and on‐site detection of illicit drugs, due to their potential for portability, high sensitivity and reusability. Three new bay‐substituted perylene diimide derivatives are synthesized , P1‐CH3 (1‐methyl), P1‐CF3 (1‐trifluoromethyl), and P1‐(CF3)2 (1,7‐di‐trifluoromethyl) that can be solution processed into thin films capable of detecting methamphetamine hydrochloride (MA•HCl) and cocaine•HCl via a luminescence quenching mechanism. The ionization potentials of the materials are sufficiently high to enable photoinduced hole transfer to occur, which led to the luminescence quenching. The trifluoromethyl‐substituted PDIs exhibit superior sensitivity and reversibility of the luminescence quenching process. In particular, P1‐(CF3)2 shows a limit of detection to MA•HCl of ≈100 ng after a 15‐second exposure, and its luminescence can be fully recovered either through mild heating or being placed in an air flow. Furthermore, by using the luminescence quenching and recovery responses of four PDI sensing materials it is possible to differentiate MA•HCl, cocaine•HCl, from aspirin, caffeine, sugar, and (sebum) skin oil in around a minute.