Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization

Giovanni Ferrara; Tienan Jin; Kazuaki Oniwa; Jian Zhao; Abdullah M. Asiri; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2011.11.132

Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization

Giovanni Ferrara, Tienan Jin, Kazuaki Oniwa, Jian Zhao, Abdullah M. Asiri, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

A new class of symmetric π-conjugated donor-acceptor-donor (D-A-D) materials, with aryl- or heteroaryl[a]annulated carbazole (AHA[a]C) moieties as the donors and with 2,1,3-benzothiadiazole (BT) as an acceptor, has been synthesized via NaAuCl ₄-catalyzed double cascade cyclization of arenyl tetraynes in ethanol in good to high yields. Photophysical and electrochemical properties of the new D-A-D materials were investigated.

Original language	English
Pages (from-to)	914-918
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.132
Publication status	Published - 2012 Feb 22

Keywords

Aryl- and heteroaryl-annulated carbazoles
Benzothiadiazole
Donor-acceptor-donor material
Double cascade cyclization
Gold catalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization",

abstract = "A new class of symmetric π-conjugated donor-acceptor-donor (D-A-D) materials, with aryl- or heteroaryl[a]annulated carbazole (AHA[a]C) moieties as the donors and with 2,1,3-benzothiadiazole (BT) as an acceptor, has been synthesized via NaAuCl 4-catalyzed double cascade cyclization of arenyl tetraynes in ethanol in good to high yields. Photophysical and electrochemical properties of the new D-A-D materials were investigated.",

keywords = "Aryl- and heteroaryl-annulated carbazoles, Benzothiadiazole, Donor-acceptor-donor material, Double cascade cyclization, Gold catalysis",

author = "Giovanni Ferrara and Tienan Jin and Kazuaki Oniwa and Jian Zhao and Asiri, {Abdullah M.} and Yoshinori Yamamoto",

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T1 - Synthesis of new donor-acceptor-donor materials via Au-catalyzed double cascade cyclization

AU - Ferrara, Giovanni

AU - Jin, Tienan

AU - Oniwa, Kazuaki

AU - Zhao, Jian

AU - Asiri, Abdullah M.

AU - Yamamoto, Yoshinori

PY - 2012/2/22

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AB - A new class of symmetric π-conjugated donor-acceptor-donor (D-A-D) materials, with aryl- or heteroaryl[a]annulated carbazole (AHA[a]C) moieties as the donors and with 2,1,3-benzothiadiazole (BT) as an acceptor, has been synthesized via NaAuCl 4-catalyzed double cascade cyclization of arenyl tetraynes in ethanol in good to high yields. Photophysical and electrochemical properties of the new D-A-D materials were investigated.

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KW - Benzothiadiazole

KW - Donor-acceptor-donor material

KW - Double cascade cyclization

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