Synthesis 2017; 49(23): 5176-5182
DOI: 10.1055/s-0036-1589088
paper
© Georg Thieme Verlag Stuttgart · New York

Practical Preparation of Octa- and Tetrabromoperylene Diimides and Derivatives Thereof

Augustina Jozeliūnaitėa, Romualdas Strielab, Linas Labanauskasb, Edvinas Orentas*a
  • aDepartment of Organic Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania
  • bCenter for Physical Sciences and Technology, Akademijos 7, 08412 Vilnius, Lithuania   Email: edvinas.orentas@chf.vu.lt
Further Information

Publication History

Received: 30 May 2017

Accepted after revision: 04 July 2017

Publication Date:
02 August 2017 (eFirst)

Dedicated to Prof. V. Snieckus on the occasion of his 80th birthday

Abstract

A mild synthesis of fully brominated perylene dianhydride and diimides in one step from easily available unsubstituted precursors is presented. The partial reduction of ortho-bromo substituents with hydrazine hydrate allowed for a gram-scale synthesis of a valuable intermediate, 1,6,7,12-tetrabromoperylene diimide. Several new twisted fully core-substituted perylene diimide derivatives having sulfur, nitrogen, or oxygen substituents were synthesized using regioselective nucleophilic substitution reactions.

Supporting Information

 
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