Study on novel photochromic systems based on chromophores with six-membered ring as central ethene bridge

A series of photochromic bisthienylethenes (BTE) chromophores with different central ethene bridges were synthesized. Up to date, the rational design of BTE have been mainly carried out on the side aryl groups. In our work, the influence of the aromaticity of the central ethene bridge on the photochromic properties was studied. Moreover, unlike in the literature where most of BTE have a five-membered ring bridge, six-membered ring bridges were used. In Chapter 1, examples of photochromes are given, along with the main definitions. Chapter 2 deals with BTTE, a BTE with a benzobisthiadiazole bridge and with excellent photochromic properties. c-BTTE, the closed isomer, exhibits excellent thermal stability in various solvents and in the solid state. Its fluorescence can be modulated by solvato- and photochromism. It eliminates the usual bias of thermal back reaction, typical of BTE with a six-membered ring ethene bridge. Chapter 3 is devoted to compounds with bridges having different aromaticities (BTE-NA, BTA and BTTA). Their fluorescence can be modulated by solvato- and photochromism. The relation between aromaticity and thermal stability was established: the low aromaticity of the central ethene bridge with benzobisthiadiazole unit leads to a thermal irreversibility for BTTA, and the small energy barrier between the parallel and anti-parallel conformers and the great difference in absorption between BTTA and c-BTTA allow the full conversion from BTTA to c-BTTA. Molecules with a benzothiadiazole bridge, designed for complexation and for switchable nonlinear optical properties were prepared (Chapters 4 and 5). However, the targeted properties were not evidenced up to now.

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Source https://theses.hal.science/tel-00846636
Author Yang, Yuheng
Maintainer CCSD
Last Updated May 10, 2026, 06:55 (UTC)
Created May 10, 2026, 06:55 (UTC)
Identifier NNT: 2012DENS0023
Language en
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 Yang, Yuheng
date 2012-06-05T00:00:00
harvest_object_id 09ca731f-a306-4ceb-9ae2-a805ac9e86e4
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2026-03-30T00:00:00
set_spec type:THESE