s-Tetrazine and triphenylamine derivatives : from design to applications

This work deals with the synthesis and the spectroscopic and electrochemical studies of donor-acceptor systems which have been designed for electrofluorochromism, two-photon absorption and photovoltaics. s-Tetrazine has been chosen as the acceptor for its high electron affinity, its emission properties and its ability to structure a layer thanks to intermolecular interactions (--stacking). Triphenylamine has been selected as the donor for its low ionization potential, its spectroscopic properties (high absorption and emission) and the easy modulation of its properties by changing the substituents. Seven triphenylamine derivatives have been synthesized as well as eighteen new multichromophoric compounds based on tetrazine and triphenylamine which have five different links and various substituents. They have been characterized by electrochemistry and spectroscopy (stationary and time-resolved). The study of the modulation of the photophysic properties with the controle of the redox state has been then done. Ten compounds having a conjugating link between the tetrazine and the tetrazine have been synthesized and characterized by electrochemistry and spectroscopy. Given their properties, six of them have been tested in two-photon absorption and two of them have been selected to be used as a donor in an organic solar cell. Moreover two reactions have been examined in depth in order to explain some unexpected synthesis results.

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Source https://theses.hal.science/tel-00957915
Author Quinton, Cassandre
Maintainer CCSD
Last Updated May 6, 2026, 02:06 (UTC)
Created May 6, 2026, 02:06 (UTC)
Identifier NNT: 2013DENS0047
Language fr
Rights https://about.hal.science/hal-authorisation-v1/
contributor Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM) ; École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
creator Quinton, Cassandre
date 2013-11-15T00:00:00
harvest_object_id de412597-f0f6-4e62-b97a-7322f5ec2e3d
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2026-03-31T00:00:00
set_spec type:THESE