Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

Sumio Maruyama; Hirofumi Hokari; Tatsuo Wada; Hiroyuki Sasabe

doi:10.1055/s-2001-17518

PAPER

Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

Sumio Maruyama*^a, Hirofumi Hokari^b, Tatsuo Wada^b,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;

Abstract

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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

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References

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