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

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• 作者：Yogendra Kumar ; Sharvan Kumar ; Sudhir Kumar Keshri ; Jyoti Shukla ; Shiv Shankar Singh ; Tejender S. Thakur ; Mitchell Denti ; Antonio Facchetti ; Pritam Mukhopadhyay
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：472-475
• 全文大小：356K
• ISSN：1523-7052

文摘

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).