A supramolecular polymer of nitroxide radicals via hydrogen bonding

Satoshi Nakajima, Eisuke Kato, Masayuki Minatozaki, Hiroyuki Nishide

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

2,2,6,6-Tetramethylpiperidinyl-N-oxy (TEMPO) is a robust nitroxide radical molecule under ambient conditions. We found that the TEMPO derivatives act as a proton acceptor to form an intermolecular hydrogen-bonding complex with many kinds of phenol or urea derivatives. ORTEP analysis of the crystals of TEMPO with the phenol derivatives indicated that hydrogen bonding could be formed between the oxygen of the nitroxide and the phenolic proton and the N-O bond of the hydrogen-bonded TEMPO was lengthened in comparison to that of the free N-O bond. The formation constant of the hydrogen-bonding complex of TEMPO with the phenol or urea derivatives in a chloroform solution was spectroscopically determined by IR to be 10-100 M-1. Hydrogen bonding of the thelechelic bis-TEMPO derivatives with thelechelic bis-phenol or bis-urea derivatives provided a supramolecular structure. The estimated molecular weights of the supramolecules in the chloroform solution, based on DOSY-NMR spectroscopy, were 3000-4000. The potential of the nitroxide radical's supramolecule as a new functional material is also described.

Original languageEnglish
Pages (from-to)1-4
Number of pages4
JournalMacromolecular Symposia
Volume304
Issue number1
DOIs
Publication statusPublished - 2011 Jun

Fingerprint

Hydrogen bonds
Polymers
phenols
Phenol
Derivatives
Phenols
ureas
polymers
hydrogen
Urea
chloroform
Chloroform
Chlorine compounds
Protons
protons
Functional materials
molecular weight
Nuclear magnetic resonance spectroscopy
nitroxyl
Hydrogen

Keywords

  • hydrogen bonding
  • macromolecular complex
  • nitroxide radical
  • radical polymer
  • supramolecular structures

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Condensed Matter Physics

Cite this

A supramolecular polymer of nitroxide radicals via hydrogen bonding. / Nakajima, Satoshi; Kato, Eisuke; Minatozaki, Masayuki; Nishide, Hiroyuki.

In: Macromolecular Symposia, Vol. 304, No. 1, 06.2011, p. 1-4.

Research output: Contribution to journalArticle

Nakajima, Satoshi ; Kato, Eisuke ; Minatozaki, Masayuki ; Nishide, Hiroyuki. / A supramolecular polymer of nitroxide radicals via hydrogen bonding. In: Macromolecular Symposia. 2011 ; Vol. 304, No. 1. pp. 1-4.
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