Journal
ORGANIC LETTERS
Volume 18, Issue 3, Pages 472-475Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03513
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Funding
- DST, Government of India [DST/SJF-02/CSA-02/2013-14, DBT-BT/PR5006/INF/153/2012]
- DST-FIST
- Binational Science Foundation (BSF) [2012250]
- CSIR
- UGC
- Division Of Mathematical Sciences
- Direct For Mathematical & Physical Scien [2012250] Funding Source: National Science Foundation
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A facile synthesis of octabromoperylene-3,4,9,10-tetracarboxylic dianhydride (Br-8-PDA) (1), its diimides (Br-8-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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