Photo‐induced Energy Transfer (PET) based chemosensing is a very elegant way for reporting the presence of an analyte in solution. This method was successfully applied to the detection of many cationic species in solutions and already appears in interesting commercial applications. In this paper we report on the preparation and host–guest chemistry of 1,3‐di(2‐pyrrolyl)azulene (5), a new azulene‐based selective PET‐like chemosensor that turns fluorescent upon binding the fluoride anion. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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.

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Cyclo[2]benzimidazole is a new host for anions that turns on its luminescence up to 150 fold upon binding. Photoexcited cyclo[2]benzimidazole undergoes an efficient non-radiative deactivation through an excited-state intramolecular proton-transfer (ESIPT) mechanism. Upon binding an anion, the ESIPT pathway is blocked, resulting in an increase in the luminescence efficiency.

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