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- Title
Dansylated Nitrile N‐Oxide as the Fluorescent Dye Clickable to Unsaturated Bonds without Catalyst.
- Authors
Oku, Yuki; Nakajima, Noriyuki; Hamada, Masahiro; Koyama, Yasuhito
- Abstract
Fluorescent polymeric materials have been exploited in the fields of aesthetical purposes, biomedical engineering, and three‐dimensional printing applications. While the fluorescent materials are prepared by the polymerization of fluorescent monomer or the blending a fluorescent dye with common polymer, the covalent immobilization of fluorescent dye onto common polymers is not the practical technique. In this paper, dansylated nitrile N‐oxide (Dansyl‐NO) has been designed and synthesized to be a stable nitrile N‐oxide as the derivative of 2‐hydroxy‐1‐naphthaldehyde. While Dansyl‐NO shows good reactivity to an alkene and an alkyne to give fluorescent Dansyl‐Ene and Dansyl‐Yne, respectively, it hardly reacts to a nitrile. The results indicate that Dansyl‐NO serves as a fluorescent dye clickable to alkenes and alkynes. To know the effects of solvent on the fluorescent properties, the UV‐vis and fluorescence spectra of Dansyl‐Ene are measured in three solvents. Dansyl‐Ene shows fluorescent solvatochromism, which appears to be red‐shifted along with the increase in solvent polarity. Poly(styrene‐co‐butadiene) directly reacts with Dansyl‐NO to give fluorescent modified SB. The emission spectrum of modified SB is blue‐shifted compared with that of Dansyl‐Ene. The blue‐shift could be possibly attributed to the presence of less polar polymer skeleton around the dansyl moieties of modified SB.
- Subjects
FLUORESCENT dyes; THREE-dimensional printing; NITRILE oxides; FLUORESCENCE spectroscopy; NITRILE derivatives; POLYMER blends; MOLECULAR spectra
- Publication
Chemistry - A European Journal, 2024, Vol 30, Issue 14, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202400092