Calix[3]carbazole: One-Step Synthesis and Host-Guest Binding

Peng Yang; Yong Jian; Xue Zhou; Gang Li; Tuo Deng; Hongyan Shen; Zhaozheng Yang; Zhangmin Tian

doi:10.1021/acs.joc.6b00252

Calix[3]carbazole: One-Step Synthesis and Host-Guest Binding

Peng Yang, Yong Jian, Xue Zhou, Gang Li, Tuo Deng, Hongyan Shen, Zhaozheng Yang, Zhangmin Tian

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38 Scopus citations

Abstract

The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C₂H₅)₄⁺ cation (tetraethylammonium, TEA) via cation-π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.

Original language	English (US)
Pages (from-to)	2974-2980
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.6b00252
State	Published - Apr 15 2016

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.6b00252

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title = "Calix[3]carbazole: One-Step Synthesis and Host-Guest Binding",

abstract = "The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C2H5)4+ cation (tetraethylammonium, TEA) via cation-π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.",

author = "Peng Yang and Yong Jian and Xue Zhou and Gang Li and Tuo Deng and Hongyan Shen and Zhaozheng Yang and Zhangmin Tian",

note = "Funding Information: We acknowledge support from the National Natural Science Foundation of China (Grant 21102095), Liaoning Provincial Natural Science Foundation (Grant 2015020752), and programs for the innovative research team of the Ministry of Education and for the Liaoning innovative research team in university. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.6b00252",

language = "English (US)",

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TY - JOUR

T1 - Calix[3]carbazole

T2 - One-Step Synthesis and Host-Guest Binding

AU - Yang, Peng

AU - Jian, Yong

AU - Zhou, Xue

AU - Li, Gang

AU - Deng, Tuo

AU - Shen, Hongyan

AU - Yang, Zhaozheng

AU - Tian, Zhangmin

N1 - Funding Information: We acknowledge support from the National Natural Science Foundation of China (Grant 21102095), Liaoning Provincial Natural Science Foundation (Grant 2015020752), and programs for the innovative research team of the Ministry of Education and for the Liaoning innovative research team in university. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/4/15

Y1 - 2016/4/15

N2 - The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C2H5)4+ cation (tetraethylammonium, TEA) via cation-π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.

AB - The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C2H5)4+ cation (tetraethylammonium, TEA) via cation-π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.

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Calix[3]carbazole: One-Step Synthesis and Host-Guest Binding

Abstract

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