Synthesis of 1,6/7-(NO 2 ) 2 -Perylenediimide and 1,6/7-(NH 2 ) 2 -Perylenediimide as Regioisomerically Pure Materials.

Autor: Gapin A; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., David AHG; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Allain M; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Masson D; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Alévêque O; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Ave T; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Le Bras L; Laboratoire Chrono-environnement (UMR 6249), Université de Franche-Comté, 16 route de Gray, 25030, Besançon, France., Hudhomme P; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France., Goujon A; Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, 49000, Angers, France.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Jun 13; Vol. 29 (33), pp. e202300652. Date of Electronic Publication: 2023 Apr 27.
DOI: 10.1002/chem.202300652
Abstrakt: The use of perylenediimide (PDI) building blocks in materials for organic electronic is of considerable interest. This popular n-type organic semiconductor is tuned by introducing peripheral groups in their ortho and bay positions. Such modifications radically alter their optoelectronic properties. In this article, we describe an efficient method to afford regioisomerically pure 1,6/7-(NO 2 ) 2 - and (NH 2 ) 2 -PDIs employing two key steps: the selective crystallization of 1,6-(NO 2 ) 2 -perylene-3,4,9,10-tetracarboxy tetrabutylester and the nitration of regiopure 1,7-Br 2 -PDI with silver nitrite. The optoelectronic properties of the resulting regioisomerically pure dinitro, diamino-PDIs and bisazacoronenediimides (BACDs) are reported and demonstrate the need to separate both regioisomers of such n-type organic semiconductors for their inclusion in advanced optoelectronic devices. For the first time, the two regioisomers of the same PDI starting material are available on the multigram scale, which will stimulate the exploration of regioisomerism/properties relationship for this family of dyes.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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