Sensitive and Selective Photoinduced‐Electron‐Transfer‐Based Sensing of Alkylating Agents

Abstract

Photoinduced-electron-transfer (PET)-based chemosensing is a very elegant way of reporting the presence of a guest species in solution. This method was successfully applied for the detection of different ionic species, such as cations, anions, and protons. Herein, we report on the application of the PET chemosensing concept for the efficient and selective detection of different alkylating agents. 2-(2-Dimethylaminoethyl)benzo[de]isoquinoline-1,3-dione (1) was found to be a highly selective and effective PET chemosensor that turns luminescent upon reacting with different alkylating agents. This PET-based system detected even rather weak alkylating agents, such as dichloromethane. A PET-based sensor that consists of 1 as the active component could detect rather low concentrations of alkylating agents in solution and in the gas phase.

Plasticization of a polymer layer harnessed to a silicon microcantilever as a highly sensitive and selective means to detect nitroaromatic derivatives

“…In such a way, the overall amount of analyte that the sensing element is exposed to is no longer dictated by the concentration of the analyte in the environment surrounding it and the formation constant of the complex between the sensing element and the analyte but rather by the absolute amount of the analyte that reacts with the sensing element. In cases where only the analyte reacts irreversibly with the sensing element while other materials react reversibly with it, both improved sensitivity and identification ability may be achieved …”

“…The combination of chemo‐mechanics and MEMS platforms offers chemo‐mechanical sensors with promising properties . Chemo‐mechanical sensors that are based on microcantilevers coated with a sensing layer have recently opened new and promising routes to the detection of different chemical as well as biological substances . The readout of the recognition events is normally done through piezo‐resistive or optical effects, both in the dynamic (following the resonant frequency shift of a microcantilever) and static (following microcantilever bending) modes.…”

Detection of Alkylating Agents Using Optical, Electrical and Mechanical Means

“…The reaction of the nucleophile with the alkylating agent needs to be transformed into a measurable signal. For example, we have recently reported on using luminescence turn-on as well as luminescence shifts for the detection and identification of different alkylating agents (Borzin et al, 2010;Tal et al, 2006). The signal needs to be analysed in a way that offers identification ability as well as some ability to assess the risk from the detected alkylator.…”

Detection and Identification of Alkylating Agents by Using a Bioinspired “Chemical Nose”

“…As the tailoring of specific and selective receptors for such small and reactive molecules seems to be an inefficient approach, previous attempts either gave up selectivity and detected all alkylating agents in a nonspecific way by relying on the color change of a nucleophile upon reaction with an alkylating agent [6][7][8] or they focused on a limited family of alkylators by detecting a specific mass or the presence of a specific atom contained in the alkylators (for example, the sulfur in mustard gas). [9] In recent years, we and other groups [10] have reported on the photoinduced electron transfer (PET) based detection of alkylating agents based on the quaternization of a Lewis base nucleophile, usually a tertiary amine group, which serves also as a quencher to the luminophore. [11,12] Nevertheless, owing to the very simple structure of these alkylators and despite the high sensitivity attained by this approach, the ability to identify the presence of specific alkylating agents is still missing, because most alkylators yield a very similar spectral response with PET systems.…”