Nanocage-Confined Synthesis of Fluorescent Polycyclic Aromatic Hydrocarbons in Zeolite

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Polycyclic aromatic hydrocarbons (PAHs) attract much attention for applications to organic light-emitting diodes, field-effect transistors, and photovoltaic cells. The current synthetic approaches to PAHs involve high-temperature flash pyrolysis or complicated step-bystep organic reactions, which lead to low yields of PAHs. Herein, we report a facile and scalable synthesis of PAHs, which is carried out simply by flowing acetylene gas into zeolite under mild heating, typically at 400 degrees C and generates the products of 0.30 g g(-1) zeolite. PAHs are synthesized via acetylene polymerization inside Ca2+-ion-exchanged Linde type A (LTA) zeolite, of which the alpha-cage puts a limit on the product molecular size as a confined-space nanoreactor. The resultant product after the removal of the zeolite framework exhibits brilliant white fluorescence emission in N-methylpyrrolidone solution. The product is separated into four different color emitters (violet, blue, green, and orange) by column chromatography. Detailed characterizations of the products by means of various spectroscopic methods and mainly mass spectrometric analyses indicate that coronene (C24H12) is the main component of the blue emitter, while the green emitter is a mixture of planar and curved PAHs. The orange can be attributed to curved PAHs larger than ovalene, and the violet to smaller molecules than coronene. The PAH growth mechanism inside Ca2+ -exchanged LTA zeolite is proposed on the basis of mass spectral analyses and density functional theory calculations.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-06
Language
English
Article Type
Article
Keywords

OLEFIN METATHESIS; CHEMISTRY; ACETYLENE

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.140, no.23, pp.7101 - 7107

ISSN
0002-7863
DOI
10.1021/jacs.8b00900
URI
http://hdl.handle.net/10203/244286
Appears in Collection
CH-Journal Papers(저널논문)
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