Color and Fluorescence Imaging with t-Boc-protected Dihydroxynaphthacenedione

Abstract

In recent years, generation of patterned images in polymer films has become a central focus in a variety fields of chemistry. Recently, generation of functional images by selective immobilization of organic dyes in the polymer film has been reported.1-3 Selective removal of acid labile protecting groups through photoinduced chemical transformation followed by chemisorption of organic dyes from solution into the patterned polymer film afforded µm-scale functional images.

Mapping Acid‐Catalyzed Deprotection in Thin Polymer Films: Fluorescence Imaging Using Prefluorescent 7‐Hydroxycoumarin Probes

“…The highly fluorescent nature of these probes allows fluorescence imaging with much lower loadings than used previously reported probes. [17,18] Varying substituents at the 3-position altered the fluorescence spectra such that a variety of differently colored images were obtained, thus providing flexibility for fluorescence microscopy applications, and a useful tool in the resolution of polymer-compatibility issues. This system may prove useful in the preparation of functional fluorescent images in polymer films and in studying lithographically relevant processes.…”

“…[17] In this case, deprotection of a hydroxyl group also results in the formation of an intramolecular hydrogen bond, but unlike the quinizarin case, the fluorescence quantum yield decreases due to quenching by an excited state intramolecular proton transfer. In both of these systems as much as 20 [17] and 50 [18] wt.-% of dye relative to the polymer matrix were used to make fluorescent images.…”

The “Precursor Approach” to Patterned Fluorescence Images in Polymer Films

“…[50][51][52][53][54] Aromatic compounds in which strong intramolecular hydrogen bonds or aromatic stacking interactions exist tend to self-aggregate when placed in common organic solvents. Owing to their poor solubilities, dissolution of these materials often requires highly polar solvents, such as DMF or DMSO.…”

The first synthesis of a transition metal-catalyzed homopolymer having pendentt-boc-protected quinizarin for patterned fluorescence images

“…This is mainly because most transition metal catalysts rapidly react with functional groups and become inactive for polymerization. As part of our on going efforts for the development of photoinduced color/fluorescence changing polymers, [13][14][15][16][17][18][19] we now report the first successful transition metal-catalyzed synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties for patterned fluorescence images.…”