PHOTOPHYSICAL CHARACTERISATION OF TRÖGER´S BASE DERIVATIVES

LENADRO TRUPP; MARIANA VARDE; JAVIER RODRIGUEZ; BEATRIZ BARJA

Villa Carlos Paz, Cordoba, ARgentina

Congreso; XIII Encuentro Latinoamericano de Fotoquímica y Fotobiología; 2017

Grupo Argentino de Fotobiologia

The interest in Tröger´s base analgues (TBs) emerged because the two aromatic rings fused to the central bicyclic framework are nearly perpendicular to each other, creating a rigid, V-shaped molecular scaffold with a distance of ca. 1 nm between the two extremities (Figure 1). In addition, TBs are chiral and fluorescent amines. Their chirality results from the very high energy barrier for the inversion of the nitrogen atoms and the fluorescence from the rigidity of the molecules. Due to these unique characteristics, Tröger?s base derivates have countless potential applications, such as molecular recognition, catalysis, supramolecular chemistry and new materials among others [1]. In the present work, four new Tröger?s base derivatives 1?4 (Figure 2) were synthetised in one to four steps, and their structures were confirmed by 1D and 2D NMR spectroscopy and mass spectrometry. Their stationary and dynamic photophysical properties were studied in hexane, dichloromethane (DCM), acetonitrile (MeCN) and ethanol (EtOH). Theoretical calculations in Hex, DCM and MeCN were carried out using DFT at Gaussian 09 package. Solvent effects were included by the formalism of the polarizable continuum model (IEF-PCM). Geometry optimization was done using the PBE0 functional together with cc-pVDZ basis set, and single-point energetic evaluation was performed using PBE0/aug-cc-pVDZ. Excited states were analyzed with TD-DFT using the same functional, basis set and formalism as before.