The synthesis and structures of arene-substituted azadipyrromethenes

We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via the well-established chalcone synthetic method. The stability and yields of these azadipyrromethenes is highly dependent on the nature of the arene substituent, with the bis-pyridine systems exhibiting the highest degree of instability. The structures of several of the compounds and their BF2 adducts are presented; intramolecular hydrogen bonding is observed in the free base ADPMs. We also present a study into the absorption and emission properties of the ADPMs and their BF2 adducts and observe that they are also highly dependent on the identity of the substituents. (C) 2015 Elsevier Ltd. All rights reserved.