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RESEARCH ARTICLE

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Fluorescent Ethenyl- and Ethynyl-dimesitylboranes Derived from 5-(Dimethylamino)-N-(prop-2-ynyl)naphthalene-1-sulfonamide

Wai-Yeung Wong ^A ^B , Suk-Yue Poon ^A , Mei-Fang Lin ^A and Wai-Kwok Wong ^A

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry and Centre for Advanced Luminescence Materials, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong, ROC.

^B Corresponding author. Email: rwywong@hkbu.edu.hk

Australian Journal of Chemistry 60(12) 915-922 https://doi.org/10.1071/CH07242
Submitted: 16 July 2007 Published: 4 December 2007

Abstract

Two new fluorescent ethenyl- and ethynyl-dimesitylboranes functionalized with a dansyl group 1 and 2 have been synthesized in good yields. Compound 1 was prepared by the hydroboration of 5-(dimethylamino)-N-(prop-2-ynyl)naphthalene-1-sulfonamide I with dimesitylborane (HB(Mes)₂) in dry tetrahydrofuran at room temperature, and compound 2 was synthesized by Pd-catalyzed cross-coupling of I with 4-I-C₆H₄B(Mes)₂. Both organoborane compounds 1 and 2 have been characterized by infrared spectroscopy, NMR spectroscopy, and mass spectrometry. The molecular structures of I and 1 were confirmed by X-ray crystallography. The electronic absorption and redox properties of 1 and 2 were investigated. They both exhibit large positive solvatochromism and their emission spectra have been recorded in a range of organic solvents with the fluorescence maxima exhibiting large bathochromic shifts in highly polar solvents, indicative of charge transfer which leads to large dipole moments in the excited state. The application of 1 as a blue fluorescent dopant in doped guest–host organic light-emitting diodes is also described.

Acknowledgements

Financial support from a CERG Grant from the Hong Kong Research Grants Council (HKBU 202005P) and a Faculty Research Grant from the Hong Kong Baptist University (FRG/05-06/II-71) is gratefully acknowledged. We thank Dr J. C. Collings and Professor T. B. Marder (Durham University) for assistance with the syntheses of the compounds.

References

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