title: Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of Halogen Bonding and Semiconducting Properties.
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).
authors.affiliation: Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
authors.forename: Yogendra
authors.initials: Y
authors.lastname: Kumar
authors.affiliation: Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
authors.forename: Sharvan
authors.initials: S
authors.lastname: Kumar
authors.affiliation: Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
authors.forename: Sudhir
authors.initials: S
authors.lastname: Kumar Keshri
authors.affiliation: Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
authors.forename: Jyoti
authors.initials: J
authors.lastname: Shukla
authors.affiliation: Molecular and Structural Biology Division, CSIR- CDRI , Lucknow 226031, India.
authors.forename: Shiv Shankar
authors.initials: SS
authors.lastname: Singh
authors.affiliation: Molecular and Structural Biology Division, CSIR- CDRI , Lucknow 226031, India.
authors.forename: Tejender S
authors.initials: TS
authors.lastname: Thakur
authors.affiliation: Polyera Corporation, Skokie, Illinois 60077, United States.
authors.forename: Mitchell
authors.initials: M
authors.lastname: Denti
authors.affiliation: Polyera Corporation, Skokie, Illinois 60077, United States.|Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.
authors.forename: Antonio
authors.initials: A
authors.lastname: Facchetti
authors.affiliation: Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University , New Delhi 110067, India.
authors.forename: Pritam
authors.initials: P
authors.lastname: Mukhopadhyay