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Open AccessCommunication

Microwave-Assisted Synthesis and Fluorescent Properties of 4-Phenyl-1,8-naphthalimide

Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON L2S 3A1, Canada
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Molbank 2020, 2020(2), M1127; https://doi.org/10.3390/M1127
Received: 1 April 2020 / Revised: 20 April 2020 / Accepted: 21 April 2020 / Published: 24 April 2020
(This article belongs to the Section Organic Synthesis)
4-Phenyl-1,8-naphthalimide was synthesized by imidation of commercially available 4-bromo-1,8-naphthalic anhydride, followed by Suzuki coupling with phenyl boronic acid, both under microwave heating. The microwave-assisted reactions were found to be faster and more efficient than reactions carried out by heating in oil-baths. While this compound was quite fluorescent in solvents such as chloroform, methanol and ethanol, it is virtually non-fluorescent in DMSO; however, upon the addition of water to DMSO solutions of this dye, fluorescence was restored, suggesting a tendency for aggregation-induced emission. The fluorescent properties of 4-phenyl-1,8-naphthalimide were found to be influenced by salt concentrations, likely as a result of hydrophobic effects. While this dye does not show binding to DNA, presence of bovine serum albumin leads to effective fluorescence quenching. View Full-Text
Keywords: aggregation-induced emission; fluorescence; microwave-assisted synthesis; 1,8-naphthalimide; solvent-dependence aggregation-induced emission; fluorescence; microwave-assisted synthesis; 1,8-naphthalimide; solvent-dependence
MDPI and ACS Style

Betancourt, F.; Helmkay, J.; Yan, H. Microwave-Assisted Synthesis and Fluorescent Properties of 4-Phenyl-1,8-naphthalimide. Molbank 2020, 2020, M1127.

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