Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Abstract

Bicolor fluorescent micro‐patterns in the polymer film are prepared through the use of a new group of photobase generator containing phthalimido carbamate groups. The photobase generation from phthalimide carbamates is studied by examining the changes in pH, fluorescence intensity, and photo‐crosslinking of poly(glycidyl methacrylate). The product analysis of a model compound indicates that amine groups are produced from the photolytic cleavage of the C–N bond of the phthalimide carbamate groups. A copolymer containing phthalimide carbamate groups is applied to a bicolor fluorescent imaging material. Red‐yellow fluorescent micropatterns are obtained by treating the copolymer film, which is irradiated with 254 nm UV light through a photomask, with fluorescamine and rhodamine, consecutively. Various colored fluorescent micropatterns – green, red, or red‐yellow, are obtained on a single polymer film by varying the excitation wavelength.

Study on synthesis and photochemical behavior of carbamate photobase generators for fluorescence imaging

“…Self‐quenching experiments of fluorescamine‐amine adducts using alkylamines show that the maximum fluorescence intensity is observed at an alkylamine concentration of 0.1 m M , in which solution the pH value is ca. 8.3–9.0 . It's worth mentioning that the pH values of PPrC and BPrC solutions are over 8.3, which are in the self‐quenching pH value range of the alkylamine.…”

“…The final concentrations are 0.6 m M for PPrC and PPhC, 1.2 m M for SPrC, and 0.1 m M for TKPrC and BPrC, respectively. The absorption band at 280–300 nm (PPrC and PPhC), 250–276 nm (SPrC), 245–310 nm (TKPrC), and 230–277 nm (BPrC) decreases upon irradiation owing to the photodecomposition of the carbamate group . Correspondingly, the band at 300–400 nm (PPrC and PPhC), 276–400 nm (SPrC), 310–400 nm (TKPrC), and 280–400 nm (BPrC) increases upon UV irradiation due to the formation of photo‐products.…”

“…In the system, green‐fluorescent fluorescein molecules were encapsulated in red‐fluorescent polydiacetylene (PDA) vesicles, and blue‐fluorescence component was introduced through the reaction between fluorescamine and the amine groups on the PDA vesicle surfaces. Won et al reported fluorescence imaging processes based on polymeric photobase generators containing oxime‐urethane groups, phthalimido carbamate groups, and anilide groups through the use of fluorescamine, in which fluorescamine function as the sensitive fluorometric determination of primary amines.…”

Formation of Various Bicolor Fluorescent Micropatterns on a Single Polymer Film Based on Concurrent Photobleaching and Photobase Generation

“…In a previous study, we reported on fluorescence imaging based on a polymeric photobase generator containing oxime–urethane groups through use of a prefluorescent dye for amino groups . Another study described a polymer containing phthalimido carbamate groups as a bicolored fluorescent imaging material . Here, we report forming various bicolored fluorescent micropatterns on a polymer film using a concurrent photobleaching reaction of anthracene groups and photobase generation of oxime–urethane groups followed by dyeing with rhodamine B (RhB) isothiocyanate using one wavelength (310 nm) photolysis.…”

“…A binary fluorescence patterned image (blue and bluish green) was fabricated using a branched‐type aromatic oxazole polymer . Red‐yellow fluorescence micropatterns have been reported using a polymeric photobase generator bearing phthalimido carbamate groups . A polydiacetylene supramolecular system that emits red, green, and blue fluorescence has been constructed .…”