1,8‐Naphthalimides as Blue Emitting Fluorophores for Polymer Materials

Abstract

The copolymerization of 1,8‐naphthalimide derivatives (as fluorophore) with acrylonitrile has been investigated. The photophysical characteristics of monomeric and polymeric fluorophores in N,N‐dimethylformamide solution have been determined and discussed. During copolymerization, no changes in the chromophoric systems of the fluorophore occur. The influence of the studied monomeric 1,8‐naphthalimide fluorophores upon the structurally bleached polyacrylonitrile has been determined. Infrared absorption characteristics of the polymerizable 4‐alkoxy‐ and 4‐allyloxy‐N‐substituted‐1,8‐naphthalimides have been measured and discussed. The effect of the substituents upon the vibration frequencies of the carbonyl and allylic groups has been established.Blue fluorescent polyacrylonitrile copolymers with 1,8‐naphthalimides side‐group.magnified imageBlue fluorescent polyacrylonitrile copolymers with 1,8‐naphthalimides side‐group.

Synthesis and Photophysical Investigations of Novel Polymerizable Blue Emitting Fluorophores – Combination of a Hindered Amine with a Benzo[de]isoquinoline‐1,3‐dione

“…In order to receive a more complete comparative picture for the influence of the hindered amine fragment in the molecule of the examined compounds on the both monomer and polymer photostability, two other not containing 2,2,6,6-tetramethylpiperidine moiety benzo-[de]isoquinoline-1,3-dione derivatives 1b (Scheme 1) and 2c (Scheme 2) synthesized before, [27,29] were involved in the present study. Scheme 1.…”

“…6-Allyloxy-2-butylbenzo[de]isoquinoline-1,3-dione 1b, 2-allyl-6-propylbenzo[de]-isoquinoline-1,3-dione 2c and 1,2,2,6,6-pentamethylpiperidin-4-ol were synthesized and purified by methods previously described. [27,29,35] Commercial methyl methacrylate (MMA, Merck) was distilled under reduced pressure in nitrogen atmosphere before use. Dibenzoyl peroxide (DBP, Fluka, 99.6%) re-crystallized from chloroform was used as an initiator of the free radical co-polymerization.…”

“…The quantum yield of fluorescence was determined on the basis of the absorption and fluorescence spectra at a concentration of 10 À5 mol Á L À1 , using quinine bisulfate (F 0 ¼ 0.55), as a standard. [27] Elemental analysis data were obtained on a Perkin-Elmer 240 automatic analyzer. The melting points were determined by means of a Kofler melting point microscope.…”

“…The presence of a polymerizable group made it feasible to polymerize with some commercial monomers, allowing obtaining copolymers with an intense blue fluorescence. [26][27][28][29][30] Photostability of the polymers is one of their most important properties. To solve the problem of polymer stabilization, a number of different stabilizers have successfully been applied.…”

Synthesis, third-order nonlinear optical (NLO) properties of polystyrene containing 1,8-naphthalimide chromophores in the side chain

“…Such phenomenon indicates that the basic chromophoric system of naphthalimide monomers does not change after the polymerization [21,22]. Figure 4 shows the emission spectra of NAOPH, NA3OPH, p(st-co-NAOPH) and p(st-co-NA3OPH) in THF solutions excited at 450 nm.…”