A new synthetic route to 5,6,11,12-tetraarylethynyltetracenes

Kei Kitamura; Kenta Asahina; Yusaku Nagai; Keshu Zhang; Shogo Nomura; Katsunori Tanaka; Toshiyuki Hamura

doi:10.1039/C8OB02450B

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A new synthetic route to 5,6,11,12-tetraarylethynyltetracenes†

Kei Kitamura,^a Kenta Asahina,^a Yusaku Nagai,^a Keshu Zhang,^a Shogo Nomura,^b Katsunori Tanaka

^bc and Toshiyuki Hamura

*^a

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
E-mail: thamura@kwansei.ac.jp

^b Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan

^c Biofunctional Chemistry Laboratory, Kazan Federal University, 18 Kremlyovskaya street, Kazan 420008, Russia

Abstract

A new synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, π-extended rubrenes, was developed via [4 + 2] cycloadditions of dialkynylisobenzofuran and 1,4-naphthoquinone. Introduction of arylethynyl groups by double nucleophilic additions to tetracenequinone gave sterically congested (arylethynyl)tetracenes after reductive aromatization. The photophysical properties of the newly prepared π-conjugated molecules are also evaluated.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB02450B
Article type: Communication
Submitted: 01 Oct 2018
Accepted: 08 Nov 2018
First published: 13 Nov 2018

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Org. Biomol. Chem., 2018,16, 9143-9146

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A new synthetic route to 5,6,11,12-tetraarylethynyltetracenes

K. Kitamura, K. Asahina, Y. Nagai, K. Zhang, S. Nomura, K. Tanaka and T. Hamura, Org. Biomol. Chem., 2018, 16, 9143 DOI: 10.1039/C8OB02450B

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Organic & Biomolecular Chemistry

A new synthetic route to 5,6,11,12-tetraarylethynyltetracenes†

Abstract

Supplementary files

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A new synthetic route to 5,6,11,12-tetraarylethynyltetracenes

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