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  • Bicarbazoles: systematic structure-property investigations on a series of conjugated carbazole dimers.

Bicarbazoles: systematic structure-property investigations on a series of conjugated carbazole dimers.

The Journal of organic chemistry (2012-09-19)
Shin-ichiro Kato, Hiroto Noguchi, Atsushi Kobayashi, Toshitada Yoshihara, Seiji Tobita, Yosuke Nakamura
ABSTRACT

A large series of conjugated carbazole dimers, namely bicarbazoles 1-12, were synthesized by Suzuki-Miyaura, Sonogashira, Hay, and McMurry coupling reactions. In 1-12, the two carbazole moieties are linked at the 1-, 2-, or 3-position directly or via an acetylenic or olefinic spacer. The structure-property relationships, particularly the effects of the conjugation connectivity and the π-conjugated spacers on the electronic, photophysical, and electrochemical properties of 1-12, were studied by extensive UV-vis and fluorescence spectroscopic measurements, cyclic voltammetry (CV), and theoretical calculations as well as X-ray crystallographic analyses. The connection at the 1-position of carbazole ensures high extent of π-conjugation, while that at the 3-position enhances the electron-donating ability. Both acetylenic and olefinic spacers allow the extension of π-conjugation, and the latter also causes the increase of the donor ability. Moreover, the structural variations were found to affect the fluorescence quantum yields significantly, which are up to 0.84.

MATERIALS
Product Number
Brand
Product Description

Supelco
Carbazole, VETRANAL®, analytical standard
Sigma-Aldrich
Carbazole, ≥95% (GC)