Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Synthesis and characterization of oxadisilole-fused 1H-benzo[f]indazoles and 1H-naphtho[2,3-f]indazoles

Language

English

Abstract

Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f]indazoles have been synthesized by the 1,3-dipolar cycloaddition reactions of benzo- or naphtho-oxabicycloalkenes with nitrile imines generated in situ from N-arylhydrazonoyl chlorides followed by deoxygenation and aromatization. The photophysical, redox and thermal properties of these compounds have been characterized. Some of the indazoles show potential as deep-blue emitters for OLED applications as a result of their high fluorescence quantum yields and good thermal stabilities. Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f] indazoles have been synthesized by the 1,3-dipolar cycloaddition of benzo- or naphtho-oxabicycloalkenes with nitrile imines followed by deoxygenation and aromatization. Their photophysical, redox and thermal properties show that some of the indazoles show potential as deep-blue emitters for OLED applications. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

Cyclic voltammetry, Cycloaddition, Fluorescence, Fused-ring systems, Heterocycles

Publication Date

2013

Source Publication Title

European Journal of Organic Chemistry

Volume

2013

Issue

15

Start Page

3005

End Page

3012

Publisher

Wiley-VCH Verlag

DOI

10.1002/ejoc.201300110

Link to Publisher's Edition

http://dx.doi.org/10.1002/ejoc.201300110

ISSN (print)

1434193X

ISSN (electronic)

10990690

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