title: Synthesis by direct arylation of thiazole-derivatives: regioisomer configurations-optical properties relationship investigation.
abstract: The synthesis of thiazole(Tz)-based regioisomer materials using selective direct arylation to avoid any protection steps has been developed. A series of trimers in which the Tz groups sandwich either an electron-rich or an electron-deficient unit, with a regioselective orientation of the respective Tz unit, has therefore been synthesized. This chemical strategy has also been followed to synthesize a second series of pentamers in which the Tz group is used as a π-conjugated bridge between an electron-rich central unit and electron-deficient end-capping groups and vice versa. On both trimers and pentamers, the effect of Tz orientation on the conjugation properties of the synthesized materials was investigated by a combination of experimental measurements and density functional theory calculations. This study highlights that control of the orientation of the Tz unit leads to the synthesis of the most conjugated regioisomer derivative. The present work gives chemical synthesis tools for the synthesis of selectively oriented Tz-based materials as well as a general guideline for the design of Tz-based materials with the highest conjugation length, including the Tz-orientation effect.
authors.affiliation: Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé (ICPEES), Département d'Ingénierie Polymère, UMR 7515 au CNRS, Ecole Européenne de Chimie, Polymères et Matériaux , 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
authors.forename: Patricia
authors.initials: P
authors.lastname: Chávez
authors.forename: Chheng
authors.initials: C
authors.lastname: Ngov
authors.forename: Pierre
authors.initials: P
authors.lastname: de Frémont
authors.forename: Patrick
authors.initials: P
authors.lastname: Lévêque
authors.forename: Nicolas
authors.initials: N
authors.lastname: Leclerc
mesh_terms: D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism; D013830:Thiadiazoles / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013830:Thiadiazoles; D013844:Thiazoles; C015700:benzo-1,2,3-thiadiazole