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Synlett 2012(7): 973-989  
DOI: 10.1055/s-0031-1290566
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Silicon-Bridged Biaryls: Molecular Design, New Synthesis, and Luminescence Control

Masaki Shimizu*a, Tamejiro Hiyamab
a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Fax: +81(75)3832445; e-Mail: m.shimizu@hs2.ecs.kyoto-u.ac.jp;
b Research & Development Initiative, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
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Received 25 October 2011
Publikationsdatum:
24. Februar 2012 (online)

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Abstract

This Account describes our contribution to the development of synthetic methods for silicon-bridged biaryls such as 9-­silafluorenes and [1]benzosilolo[3,2-b][1]indoles and the photophysical characteristics of compounds obtained using these brand-new syntheses, along with those of 4,5-silicon-bridged silafluorenes prepared using the conventional synthesis.

1 Introduction

2 Design, Preparation, and Photophysical Properties of Silicon-Bridged Silafluorenes

2.1 Molecular Design

2.2 Synthesis

2.3 Structures

2.4 Photophysical Properties

3 Palladium-Catalyzed Intramolecular Coupling of 2-(Aryl­silyl)aryl Triflates: New Synthetic Method for Silicon-Bridged Biaryls

3.1 Reaction Design

3.2 Optimization and Scope

3.3 Synthetic Methods for 9-Silafluorenes Developed by Other Groups

4 Photophysical Properties of Functionalized 9-Silafluorenes

4.1 Violet-Emissive 9-Silafluorenes

4.2 D-π-A-type 9-Silafluorenes

5 Palladium-Catalyzed Intramolecular Coupling of 2-(2-Indolylsilyl)aryl Triflates through 1,2-Silicon Migration

5.1 Discovery

5.2 Scope and Mechanism

6 Photophysical Properties of Silicon-Bridged 2-Arylindoles

6.1 Fluorescence

6.2 Comparison with Carbon Analogue

7 Conclusion

Keywords

arenes - cyclization - fluorescence - materials - silicon

    References and Notes

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23

Unpublished result.

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Fluorescence of 7 in cyclohexane was very weak (λmax = 451 nm, Φ = 0.02).

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Shimizu, M.; Mochida, K.; Katoh, M.; Hiyama, T. Sci. China Chem. 2011, 54, 1937.

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The structure and properties of the bis(dimethylsilylene) analogue of 9r and its polysubstituted derivatives were studied independently by Xu [²0c] and Murakami, [²7] respectively, including solution-phase absorption and fluorescence, but not solid-state fluorescence.

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Dielectric constants of solvents are as follows: 2.02 (cyclohexane), 2.28 (benzene), 9.08 (CH2Cl2), 25.07 (EtOH), 38.8 (MeCN), and 48.9 (DMSO).