Dendritic structure having a potential gradient: New synthesis and properties of carbazole dendrimers

Ken Albrecht, Kimihisa Yamamoto

Research output: Contribution to journalArticle

127 Citations (Scopus)

Abstract

A new synthetic route for carbazole dendrimers was discovered using the copper-catalyzed N-arylation reaction. This synthetic route allowed synthesizing the fourth generation carbazole dendrimer and several derivatives for the first time. The crystal structure, Mark-Houwink-Sakurada plots, and UV-vis and fluorescence studies showed that the dendritic carbazole backbone has a rigid and highly twisted structure. From the measurement of the redox potential of the ferrocene derivatives, the IR spectra of the benzophenone derivatives, and complexation behavior of the phenylazomethine derivatives, the inductive electron-withdrawing effect of the carbazole dendron was revealed. This suggested that the summation of this electron withdrawal from each layer may produce a potential gradient such that the outer layer is electron-rich and the inner layer is electron-poor in the carbazole dendron. By assignment of the 1H and 13C NMR spectra of the dendron, the existence of this kind of potential gradient was proved. Overall, these data show the π-polarization substituent effect of the carbazole unit, and their summation determines the potential gradient in the repeating dendritic structure of the carbazole dendrimer.

Original languageEnglish
Pages (from-to)2244-2251
Number of pages8
JournalJournal of the American Chemical Society
Volume131
Issue number6
DOIs
Publication statusPublished - Feb 18 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Dendritic structure having a potential gradient: New synthesis and properties of carbazole dendrimers'. Together they form a unique fingerprint.

  • Cite this