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A Triphenylamine with Two Phenoxy Radicals Having Unusual Bonding Patterns and a Closed-Shell Electronic State.

Authors
  • Sakamaki, Daisuke
  • Yano, Soichiro
  • Kobashi, Toshiyuki
  • Seki, Shu
  • Kurahashi, Takuya
  • Matsubara, Seijiro
  • Ito, Akihiro
  • Tanaka, Kazuyoshi
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Jul 06, 2015
Volume
54
Issue
28
Pages
8267–8270
Identifiers
DOI: 10.1002/anie.201502949
PMID: 26013287
Source
Medline
Keywords
License
Unknown

Abstract

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.

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