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Kumar Y, Kumar S, Kumar Keshri S, et al. Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties. Org Lett. 2016;18(3):472-5doi: 10.1021/acs.orglett.5b03513.
Kumar, Y., Kumar, S., Kumar Keshri, S., Shukla, J., Singh, S. S., Thakur, T. S., Denti, M., Facchetti, A., & Mukhopadhyay, P. (2016). Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties. Organic letters, 18(3), 472-5. https://doi.org/10.1021/acs.orglett.5b03513
Kumar, Yogendra, et al. "Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties." Organic letters vol. 18,3 (2016): 472-5. doi: https://doi.org/10.1021/acs.orglett.5b03513
Kumar Y, Kumar S, Kumar Keshri S, Shukla J, Singh SS, Thakur TS, Denti M, Facchetti A, Mukhopadhyay P. Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties. Org Lett. 2016 Feb 05;18(3):472-5. doi: 10.1021/acs.orglett.5b03513. Epub 2016 Jan 15. PMID: 26771262.
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Org Lett. 2016 Feb 05;18(3):472-5. doi: 10.1021/acs.orglett.5b03513. Epub 2016 Jan 15.

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

Organic letters

Yogendra Kumar, Sharvan Kumar, Sudhir Kumar Keshri, Jyoti Shukla, Shiv Shankar Singh, Tejender S Thakur, Mitchell Denti, Antonio Facchetti, Pritam Mukhopadhyay

Affiliations

  1. Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
  2. Molecular and Structural Biology Division, CSIR- CDRI , Lucknow 226031, India.
  3. Polyera Corporation, Skokie, Illinois 60077, United States.
  4. Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.

PMID: 26771262 DOI: 10.1021/acs.orglett.5b03513

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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