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Synthesis 2001(12): 1794-1799
DOI: 10.1055/s-2001-17518
PAPER
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

Sumio Maruyama*a, Hirofumi Hokarib, Tatsuo Wadab,c, Hiroyuki Sasabe*b,d
a Japan Science and Technology Corporation (JST), c/o Nanotechnology Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
b Core Research for Evolutional Science and Technology (CREST), Japan Science and Technology Corporation (JST), c/o Supramolecular Science Laboratory, RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
c Supramolecular Science Laboratory, RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
d Department of Photonics Material Science, Chitose Institute of Science and Technology, 758-65 Bibi, Chitose, Hokkaido 066-8655, Japan
Fax: +81(298)616296; e-Mail: maruyama-s@aist.go.jp;
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Publication History

Received 18 May 2001
Publication Date:
11 August 2004 (online)

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Abstract

The syntheses of novel cyclic oligomers based on the carbazolylacetylene unit are described. The desired cyclic tetramer could be synthesized in 14.3% yield by the reaction of 3,6-diethynyl-9-tetradecylcarbazole and 3,6-bis(3’-iodo-9’-tetradecylcarbazolyl)-9-tetradecylcarbazole in the presence of Pd(PPh3)4/CuI as catalysts under high dilution conditions and purified by column chromatography and isolated by preparative gel permeation chromatography. Besides the tetramer, a cyclic octamer was also isolated in 5.4% yield.

Key words

cross-coupling - cyclizations - macrocycles - carbazolylacetylene - cyclic oligomers