Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties

Organic Letters
Yogendra KumarPritam Mukhopadhyay

Abstract

A facile synthesis of octabromoperylene-3,4,9,10-tetracarboxylic dianhydride (Br8-PDA) (1), its diimides (Br8-PDIs) (2a-e), and bis-, tris-, and tetra-amino substituted diimides (5a-c) with six, five, and four remaining substitutable Br atoms, respectively, is reported. Octabromination results in facile chemical/electrochemical reduction, radical anion formation, and red-shifted optical properties. For the first time, diverse halogen-bonding interactions were identified in the PDA/PDI, which along with the attractive electronic features enhance the electron-transport characteristics compared to the di-/tetra-brominated PDIs (3/4).

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Citations

Aug 3, 2016·The Journal of Physical Chemistry Letters·Bao ZhaWenli Deng
Apr 1, 2017·Journal of the American Chemical Society·Seth A SharberSamuel W Thomas Iii
Feb 1, 2019·Chemistry : a European Journal·Sharvan KumarPritam Mukhopadhyay
Sep 19, 2019·Chemistry : a European Journal·Lutz GadeHubert Wadepohl
Apr 17, 2020·Chemical Communications : Chem Comm·Gilles BergerFranck Meyer

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