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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10.1016/j.tetlet.2011.11.132

Cite this

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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",

note = "Funding Information: We thank the faculty members of the Instrumental Analysis Center at Tohoku University for the measurement of NMR and mass spectra. This work was supported by World Premier International Research Center Initiative (WPI), MEXT, Japan. ",

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doi = "10.1016/j.tetlet.2011.11.132",

language = "English",

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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

N1 - Funding Information: We thank the faculty members of the Instrumental Analysis Center at Tohoku University for the measurement of NMR and mass spectra. This work was supported by World Premier International Research Center Initiative (WPI), MEXT, Japan.

PY - 2012/2/22

Y1 - 2012/2/22

N2 - 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.

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.

KW - Aryl- and heteroaryl-annulated carbazoles

KW - Benzothiadiazole

KW - Donor-acceptor-donor material

KW - Double cascade cyclization

KW - Gold catalysis

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VL - 53

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EP - 918

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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

Abstract

Keywords

ASJC Scopus subject areas

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