Issue 29, 2013

Tunable electronic interactions between anions and perylenediimide

Abstract

Over the past decade anion–π interaction has emerged as a new paradigm of supramolecular chemistry of anions. Taking advantage of the electronic nature of anion–π interaction, we have expanded its boundaries to charge-transfer (CT) and formal electron transfer (ET) events by adjusting the electron-donating and accepting abilities of anions and π-acids, respectively. To establish that ET, CT, and anion–π interactions could take place between different anions and π-acids as long as their electronic and structural properties are conducive, herein, we introduce 3,4,9,10-perylenediimide (PDI-1) that selectively undergoes thermal ET from strong Lewis basic hydroxide and fluoride anions, but remains electronically and optically silent to poor Lewis basic anions, as ET and CT events are turned OFF. These interactions have been fully characterized by UV/Vis, NMR, and EPR spectroscopies. These results demonstrate the generality of anion-induced ET events in aprotic solvents and further refute a notion that strong Lewis basic hydroxide and fluoride ions can only trigger nucleophilic attack to form covalent bonds instead of acting as sacrificial electron donors to π-acids under appropriate conditions.

Graphical abstract: Tunable electronic interactions between anions and perylenediimide

Supplementary files

Article information

Article type
Paper
Submitted
08 Apr 2013
Accepted
22 May 2013
First published
23 May 2013

Org. Biomol. Chem., 2013,11, 4797-4803

Tunable electronic interactions between anions and perylenediimide

F. S. Goodson, D. K. Panda, S. Ray, A. Mitra, S. Guha and S. Saha, Org. Biomol. Chem., 2013, 11, 4797 DOI: 10.1039/C3OB40703A

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