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

Ismaël Rabouel; Nicolas Richy; Anissa Amar; Abdou Boucekkine; Thierry Roisnel; Olivier Mongin; Mark G. Humphrey; Frédéric Paul

doi:10.3390/MOLECULES25225475

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

Ismaël Rabouel, Nicolas Richy, Anissa Amar, Abdou Boucekkine^*, Thierry Roisnel, Olivier Mongin, Mark G. Humphrey^*, Frédéric Paul^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Article number	5475
Journal	Molecules
Volume	25
Issue number	22
DOIs	https://doi.org/10.3390/MOLECULES25225475
Publication status	Published - 1 Nov 2020

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@article{006de60f417d48cf8ba22d2e69ffc3ae,

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

abstract = "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.",

keywords = "DFT calculations, cyclic thioureas, cyclic urea, isocyanurates, linear optics, thioisocyanurates, thionation",

author = "Isma{\"e}l Rabouel and Nicolas Richy and Anissa Amar and Abdou Boucekkine and Thierry Roisnel and Olivier Mongin and Humphrey, {Mark G.} and Fr{\'e}d{\'e}ric Paul",

note = "Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = nov,

day = "1",

doi = "10.3390/MOLECULES25225475",

language = "English",

volume = "25",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - 1,3,5-Triaryl-1,3,5-Triazinane-2,4,6-Trithiones

T2 - Synthesis, Electronic Structure and Linear Optical Properties

AU - Rabouel, Ismaël

AU - Richy, Nicolas

AU - Amar, Anissa

AU - Boucekkine, Abdou

AU - Roisnel, Thierry

AU - Mongin, Olivier

AU - Humphrey, Mark G.

AU - Paul, Frédéric

PY - 2020/11/1

Y1 - 2020/11/1

N2 - 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.

AB - 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.

KW - DFT calculations

KW - cyclic thioureas

KW - cyclic urea

KW - isocyanurates

KW - linear optics

KW - thioisocyanurates

KW - thionation

UR - http://www.scopus.com/inward/record.url?scp=85096817652&partnerID=8YFLogxK

U2 - 10.3390/MOLECULES25225475

DO - 10.3390/MOLECULES25225475

M3 - Article

SN - 1420-3049

VL - 25

JO - Molecules

JF - Molecules

IS - 22

M1 - 5475

ER -

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

Abstract

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