Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives

M J Plater, M McKay, T Jackson

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline.

Original languageEnglish
Pages (from-to)2695-2701
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 2000

Keywords

  • AMORPHOUS MOLECULAR MATERIALS
  • METHYL-SUBSTITUTED DERIVATIVES
  • STARBURST MOLECULES
  • CATION RADICALS
  • HOLE MOBILITY
  • 1,3,5-TRIS(DIPHENYLAMINO)BENZENE
  • TRANSITION
  • IONS

Cite this

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title = "Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives",
abstract = "The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline.",
keywords = "AMORPHOUS MOLECULAR MATERIALS, METHYL-SUBSTITUTED DERIVATIVES, STARBURST MOLECULES, CATION RADICALS, HOLE MOBILITY, 1,3,5-TRIS(DIPHENYLAMINO)BENZENE, TRANSITION, IONS",
author = "Plater, {M J} and M McKay and T Jackson",
year = "2000",
language = "English",
pages = "2695--2701",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

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TY - JOUR

T1 - Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives

AU - Plater, M J

AU - McKay, M

AU - Jackson, T

PY - 2000

Y1 - 2000

N2 - The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline.

AB - The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline.

KW - AMORPHOUS MOLECULAR MATERIALS

KW - METHYL-SUBSTITUTED DERIVATIVES

KW - STARBURST MOLECULES

KW - CATION RADICALS

KW - HOLE MOBILITY

KW - 1,3,5-TRIS(DIPHENYLAMINO)BENZENE

KW - TRANSITION

KW - IONS

M3 - Article

SP - 2695

EP - 2701

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

ER -