Supramolecular Gel Phase Controlled [4 + 2] Diels–Alder Photocycloaddition for Electroplex Mediated White Electroluminescence

Diels–Alder photocycloaddition of 9-phenyl­ethynyl­anthracene results in multiple [4 + 2] and [4 + 4] cycloaddition products in solution, which can be controlled to form specific products under a restricted environment. We have exploited the gel phase of a 9-phenylethynyl­anthracence derivative as a...

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Veröffentlicht in:Journal of the American Chemical Society 2019-04, Vol.141 (14), p.5635-5639
Hauptverfasser: Das, Satyajit, Okamura, Naoki, Yagi, Shigeyuki, Ajayaghosh, Ayyappanpillai
Format: Artikel
Sprache:eng
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Zusammenfassung:Diels–Alder photocycloaddition of 9-phenyl­ethynyl­anthracene results in multiple [4 + 2] and [4 + 4] cycloaddition products in solution, which can be controlled to form specific products under a restricted environment. We have exploited the gel phase of a 9-phenylethynyl­anthracence derivative as a confined medium to specifically yield the [4 + 2] cycloadduct in >90% yield. The photocycloadduct (anti-form) exhibited a blue emission with CIE chromaticity of x = 0.16/y = 0.16. Construction of an organic light emitting device with the photocycloadduct, using a carbazole-based hole transporting host, resulted in white light emission with a CIE chromaticity of x = 0.33/y = 0.32. This observation not only highlights the use of gel chemistry to achieve the otherwise difficult to obtain photoproducts but also underlines their potential in optoelectronic device fabrication.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b00955