Synthesis, characterization, and emulsion polymerization of polymerizable coumarin derivatives

Abstract

We describe the synthesis of a new polymerizable coumarin derivative, [6‐(β‐acryloxyethoxy)‐7‐isopropoxy‐4‐methyl coumarin (3)], whose UV absorption spectrum significantly overlaps the emission spectrum of 9‐alkyl phenanthrene chromophore. This dye can serve several purposes in latex films. It can be a tracer for fluorescence microscopy experiments, or it can act as a donor or acceptor dye in nonradiative energy transfer experiments. Here we emphasize its role as an energy transfer acceptor in experiments with phenanthrene as the corresponding donor. Coumarin‐labeled poly(butyl methacrylate) latex dispersions could be synthesized by conventional batch emulsion polymerization with complete monomer conversion, complete dye incorporation, and uniform dye distribution. Attempts to extend this reaction to poly(vinyl acetate) copolymers failed because the dye inhibited monomer conversion. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3479–3489, 2004

Preparation and fluorescent properties of poly(vinyl alcohol) bearing coumarin

“…4 Materials containing a coumarin component have been useful in many fields due to their characteristics of high emission yield, excellent photo-stability, and extended spectral range, such as fluorescent images, 5 non-linear optical materials, 6 liquid crystals, 7 and fluorescent labels for fluorescence energy transfer experiments. 8 7-Hydroxy-4-methyl coumarin (7-HMC) and its derivatives are strongly fluorescent laser dyes, whose ground state and excited state photophysical properties have been the subject of many studies. [9][10][11][12][13] Desai et al 14 have synthesized 4-methyl-7-(2,3expoxypropoxy) coumarin (MEC).…”

Biotransformation of 4-methylcoumarins by cambial meristematic cells of Camptotheca acuminata

“…The structure of III-1 was determined as 6-hydroxy-7-methoxyl-4-methylcoumarin based on the comparison of the NMR spectra with known compound. 28 Compound 13 C NMR spectra of compound IV-1 were similar to that of compound IV, and the major differences were the presence of signals for a sugar residue, namely d Table 2).…”

Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

“…First, our key intermediate was the dipolarophiles 2 and 3, which can easily be obtained by O-propargylation and O-allylation 41,42 , respectively of 4-methylumbelliferone 1 in one step (Scheme 1). Indeed, in our investigation, dimethylformamide was found to be an excellent solvent for the reaction of allyl and propargylbromide with 4-methylumbelliferone 1, in the presence of NaH.…”