Supramolecular BODIPY based dimers: synthesis, computational and spectroscopic studies

The synthetic procedures for the preparation of supramolecular BODIPY dimers decorated with complementary patterns able to induce the formation of a triple hydrogen bond through mutual interactions are here reported. The BODIPY and styryl-equipped BODIPY species have been suitably functionalized in meso position with 2,6-diacetamido-4-pyridyl and 1-butyl-6-uracyl moieties. Dimers and monomers have been subjected to computational and photophysical investigations in solvent media. Various peculiarities concerning the effects of the interaction geometry on the stability of the H-bonded systems have also been investigated. The combination of modelling and experimental data provides a paradigm for improving and refining the BODIPY synthetic pathway to have chromophoric architectures with a programmable supramolecular identity. Furthermore, the possibility of assembling dimers of different dyes through H-bonds could be appealing for a systematic investigation of the principal factors affecting the dynamics of the energy migration and possibly driving coherent transfer mechanisms. Our work highlights how the chemical versatility of these dyes can be exploited to design new BODIPY-based supramolecular architectures.

Automated summary

The study presents a method for preparing supramolecular BODIPY dimers capable of forming triple hydrogen bonds through interactions. Computational and photophysical properties of dimers and monomers show variations in different solvent media. Investigating the effects of interaction geometry on the stability of hydrogen-bonded systems is also emphasized.