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

• Published in: Journal of the American Chemical Society Vol. 141; no. 14; pp. 5635 - 5639
• Main Authors: Das, Satyajit, Okamura, Naoki, Yagi, Shigeyuki, Ajayaghosh, Ayyappanpillai
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 10.04.2019; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; color; cycloaddition reactions; electrochemiluminescence; gels; Physical Sciences; Science & Technology; white light; LIGHT; ENHANCEMENT; EXCIMER PHOSPHORESCENCE; PHOTOCHEMISTRY; PI; SINGLE-EMITTING-COMPONENT; COMPLEXES BEARING; EMISSION; PHOTOCYCLODIMERIZATION
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/jacs.9b00955

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.