A Triphenylamine with Two Phenoxy Radicals Having Unusual Bonding Patterns and a Closed‐Shell Electronic State1. Issue 28 (27th May 2015)

• Record Type: Journal Article
• Authors: Sakamaki, Daisuke; Yano, Soichiro; Kobashi, Toshiyuki; Seki, Shu; Kurahashi, Takuya; Matsubara, Seijiro; Ito, Akihiro; Tanaka, Kazuyoshi
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 28(2015)
• Page Start: 8267
• Page End: 8270
• Publication Date: 2015-05-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201502949
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Reported herein is the structure and the electronic properties of a novel triphenylamine derivative having two phenoxy radicals appended to the amino nitrogen atom. X‐ray single crystal analysis and the magnetic resonance measurements demonstrates the unexpected closed‐shell electronic structure, even at room temperature, of the molecule and two unusual CN bonds with multiple‐bond character. The theoretical calculations support the experimentally determined molecular geometry with the closed‐shell electronic structure, and predicted a small HOMO–LUMO gap originating from the nonbonding character of the HOMO. The optical and electrochemical measurements show that the molecule has a remarkably small HOMO–LUMO gap compared with its triphenylamine precursor.</p> </abstract>