On the versatility of electronic structures in polymethine dyes

Simon Pascal (1) , Alexandre Haefele (1) , Cyrille Monnereau (1) , Azzam Charaf-Eddin (2) , Denis Jacquemin (3) , Boris Le Guennic (4) , Olivier Maury (1) , Chantal Andraud (1)

1 LC - Laboratoire de Chimie - UMR5182
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
3 UN - Université de Nantes
4 ISCR - Institut des Sciences Chimiques de Rennes

This article provides an overview of the photophysical behavior diversity of polymethine chromophores which are ubiquitous in biological imaging and material sciences. One major challenge in this class of chromophore is to correlate the chemical structure to the observed optical properties, especially when symmetry-breaking phenomena occur. With the constant concern for rationalization of their spectroscopy, we propose an extended classification of polymethine dyes based on their ground state electronic configuration using three limit forms namely: cyanine, dipole and bis-dipole. The chemical modifications of the dye and the influence of exogenous parameters can promote dramatic spectroscopic changes that can be correlated to significant electronic reorganization between the three-abovementioned forms. The deep understanding of such phenomena should allow to identify, predict and take advantage of the versatile electronic structure of polymethines.

Mots clés: Polymethine; near-infrared dyes; cyanine; dipole; bis-dipole; spectroscopy; electronic absorption

Domaines: Chimie théorique et/ou physique

Simon Pascal, Alexandre Haefele, Cyrille Monnereau, Azzam Charaf-Eddin, Denis Jacquemin, et al.. On the versatility of electronic structures in polymethine dyes. SPIE Security + Defence, 2014, Amsterdam, Netherlands. ⟨10.1117/12.2072624⟩. ⟨hal-01896789⟩