1,3,5-Triaryl-1,3,5-Triazinane-2,4,6-Trithiones: Synthesis, Electronic Structure and Linear Optical Properties

Ismaël Rabouel (1) , Nicolas Richy (1) , Anissa Amar (2, 3) , Abdou Boucekkine (1) , Thierry Roisnel (1) , Olivier Mongin (1) , Mark G Humphrey (4) , Frédéric Paul (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 USTHB - Université des Sciences et de la Technologie Houari Boumediene = University of Sciences and Technology Houari Boumediene [Alger]
3 UMMTO - Université Mouloud Mammeri [Tizi Ouzou]
4 ANU - Australian National University

The synthesis of four new 1,3,5-triaryl-1,3,5-triazinane-2,4,6-trithione derivatives (thioisocyanurates) and two new partially thionated analogues from the corresponding 1,3,5-triaryl-1,3,5-triazinane-2,4,6-triones (isocyanurates) is reported, together with their spectroscopic properties. DFT calculations and comparison with the corresponding isocyanurates evidence the impact of the oxygen-for-sulfur replacement on the electronic structure and linear optical properties of these heterocycles. A bathochromic shift of the absorption bands and more efficient quenching of the fluorescence was observed.

Mots clés: DFT calculations; cyclic thioureas; cyclic urea; isocyanurates; linear optics; thioisocyanurates; thionation

Domaines: Chimie

Ismaël Rabouel, Nicolas Richy, Anissa Amar, Abdou Boucekkine, Thierry Roisnel, et al.. 1,3,5-Triaryl-1,3,5-Triazinane-2,4,6-Trithiones: Synthesis, Electronic Structure and Linear Optical Properties. Molecules, 2020, 25 (22), ⟨10.3390/molecules25225475⟩. ⟨hal-03038019⟩