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

Author:
Das, Satyajit, Okamura, Naoki, Yagi, Shigeyuki, Ajayaghosh, Ayyappanpillai
Source:
Journal of the American Chemical Society 2019 v.141 no.14 pp. 5635-5639
ISSN:
1520-5126
Subject:
color, cycloaddition reactions, electrochemiluminescence, gels, white light
Abstract:
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.
Agid:
6368058