25952-50-5

Usage

Uses

Used in Polymer Synthesis:
2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl)ethyl methacrylate is used as a monomer in polymer synthesis for the production of functionalized polymers. Its methacrylate group allows it to participate in polymerization reactions, creating polymers with specific properties.
Used in Drug Discovery:
In the pharmaceutical industry, 2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl)ethyl methacrylate is used as a building block in drug discovery. Its unique structure and functional groups make it a valuable component in the development of new pharmaceuticals.
Used in Material Science:
2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl)ethyl methacrylate is utilized in material science as a component for developing advanced materials. Its complex molecular structure and functional groups contribute to the creation of materials with novel properties.

Upstream product

• 98352-39-7 C₂₄H₂₄N₂O₅ 
• 79-41-4 poly(methacrylic acid) 
• 16111-07-2 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-ethanol 
• 169233-07-2 (S)-(-)-methacryloyl-L-lactic acid 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 97-51-8 5-Nitrosalicylaldehyde 
• 920-46-7 Methacryloyl chloride 
• 29636-94-0 1-(2-hydroxyethyl)-2,3,3-trimethyl-3H-indol-1-ium bromide 

Downstream Products

• 98352-39-7 C₂₄H₂₄N₂O₅ 
• 87495-24-7 C₂₄H₂₄N₂O₅ 

Relevant academic research and scientific papers

Photoreponsive Hybrid Nanoparticles with Inherent FRET Activity

The photoactivated inherent fluorescence resonance energy transfer (FRET) properties of a hard-and-soft hybrid nanosystem comprising poly(1′-(2-methacryloxyethyl)-3′,3′-dimethyl-6-nitrospiro-(2H-1-benzopyran-2,2′-indoline))-co-poly[2-(dimethylamino)ethyl methacrylate] (PSPMA-co-PDMAEMA) random copolymer brushes on silica nanoparticles are described. This unique FRET process is switched on by the simultaneous generation of isomer X and merocyanine (MC), which are bipolar in nature and comprise donor-acceptor dyads, from a single spiropyran (SP) chromophore upon UV irradiation. These X-MC species exhibit sufficient lifetimes to allow the read-out of the FRET process. The phenomenon is gradually switched off because of the thermal relaxation of the bipolar chromophores. This inherent property of the nanoemitters is employed in the development of biosensors of high specificity by monitoring variations in the FRET efficiency and lifetime of the hybrids in the presence of biological substances. More specifically, bovine serum albumin (BSA) augments the formation of MC species and retards the MC photobleaching process, leading to the enhancement of the FRET efficiency and lifetime, respectively. On the other hand, amino acid l-histidine further retards the MC thermal relaxation and prolongs the FRET process. We envisage that this platform opens new perspectives in the development of novel, optical nanosensors for applications in various fields including healthcare products and environmental monitoring.

Synthesis and characterization of new spiropyran micrometer-sized photochromic fluorescent polymeric particles of narrow size distribution by a swelling process

Photochromic fluorescent uniform micrometer-sized particles were prepared in two ways: (1) Swelling of polystyrene (PS) and poly(styrene-butylmethacrylate) (P(S-BMA)) template particles with spiropyran dye (FSP) to obtain PS/FSP and P(S-BMA)/FSP uniform particles; (2) A similar swelling process, replacing FSP by AIBN, styrene and a spiropyran monomer (MSP), followed by co-polymerization of the monomers within the swollen microspheres to obtain P(S-BMA)/P(S-MSP) uniform particles. The spiropyran dyes are not fluorescent in water or in non-polar organic solvents. In contrast, the dyes encapsulated within the particles exhibit strong red fluorescence in the merocyanine conformation. Fluorescence measurements reveal that the P(S-BMA)/FSP microspheres exhibit higher fluorescence than the PS/FSP particles. The microspheres aqueous dispersion was exposed to alternate UV and visible light cycles and it was found that the fluorescence intensity of the PS/FSP and the P(S-BMA)/FSP particles decreased by 30% of its original value after 5 photoswitching cycles while that of the P(S-BMA)/P(S-MSP) particles remained the same.

Reversible photoswitching aggregation and dissolution of spiropyran-functionalized copolymer and light-responsive FRET process

Well-defined, reversibly light-responsive amphiphilic diblock copolymer grafted with spiropyran, was prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. The copolymer self-assembles into polymeric micelles in water and exhibits reversible dissolution and re-aggregation characteristics upon ultraviolet (UV) and visible (Vis)-light irradiation. The fluorescence response of spiropyran immobilized onto the copolymer was light switchable. When nitrobenzoxadiazolyl derivative (NBD) dyes are encapsulated into the core of the micelles, a reversible, light-responsive, dual-color fluorescence resonance energy transfer (FRET) system is constructed and processed, which is well regulated by alternatively UV/vis irradiation. We anticipate these photoswitchable and FRET lighting up nanoparticles will be useful in drug delivery and cell imaging or tracking synchronously.

Spectroscopic analysis of metal ion binding in spiropyran containing copolymer thin films

In this article, we describe the synthesis and characterization of a series of spiropyran containing copolymers that were used as colorimetric sensors for a series of divalent metal ions. The composition of spiropyran contained in the polymer backbone was varied from 10?100 mol % to investigate the influence of free volume and sterics on the photochromic response. Fourier transform-infrared (FT-IR) spectroscopy was used to characterize the photoinduced conversion, as well as the merocyanine?metal ion (MC?M2+) interaction. FT-IR spectra were analyzed using chemometric methods to elucidate the chemical binding environment between MC and M2+ and to selectively identify different metal ions bound to MC. By means of UV?vis absorption spectroscopy, we also demonstrate that each metal ion gives rise to a unique colorimetric response that is dependent on the amount of spiropyran comonomer contained in the polymer backbone and that by increasing the concentration of chromophore in the copolymer, the selectivity between different metal ions decreases. With the use of chemometric methods, UV?vis spectra can be analyzed to quantitatively identify metal ions in a concentration range from 1 ?M to 100 mM.

Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

Photoswitchable fluorescent polymeric nanoparticles (PFPNs) with controllable molecular weight, high contrast, biocompatibility, and prominent photostability are highly desirable but still scarce for rewritable printing, super-resolution bioimaging, and r

Photo, pH, and thermo triple-responsive spiropyran-based copolymer nanoparticles for controlled release

A spiropyran-based amphiphilic random copolymer was synthesized and self-assembled into photo-, pH-, and thermo-responsive micellar nanoparticles. The triple-stimuli triggered morphological changes of the nanoparticles were revealed by TEM and DLS. Highly efficient controlled release of encapsulated molecules, coumarin 102, from the nanoparticles under stimulation of UV light, acid and the combined stimuli could be realized.

Synthesis of photochromic monomers derived from 1′-(2- methacryloxyethyl)-3,3-dimethyl-2-[2H]-spirobenzopyran indoline

The syntheses of five photochromic monomers derived from N- (2-methacryloxyethyl)-3′, 3′-dimethylspiro-[2H-1] benzopyrane-2,2′-indoline are reported. The preparation of these compounds involves the heterogeneous reaction between the N-(hydroxyethyl)-2,3,3- trimethylindolenonium bromide and methacryloyl chloride in a polar solvent. The esterificated salt is easily purified by crystallization in chloroform-hexane. Further condensation with the proper 2-hydroxybenzaldehyde produces the photochromic monomer in high yield. This method can also be applied in the preparation of other spiropyrane derivatives.

Unlocking Chemically Encrypted Information Using Three Types of External Stimuli

Encryption is critical to information security; however, existing chemical-based information encryption strategies are still in their infancy. We report here a new approach to chemical encryption involving a supramolecular gel QR (quick response) code wit

Photoactive nano composite as well as preparation method thereof and application thereof

The invention discloses photoactive nano composite as well as a preparation method thereof and application thereof. The nano composite is prepared from nucleic acid molecules and a cationic polymer; the cationic polymer consists of a positive electrical chain segment, a hydrophilic chain segment, and a photosensitive chain segment which is a spiropyrane chain segment. The preparation method for the nano composite comprises the steps of putting the cationic polymer solution in ultraviolet light to irradiate, then, mixing the cationic polymer solution with nucleic acid molecules, and standing toobtain the photoactive nano composite. The preparation method has the advantage that the photoactive nano composite is formed by spontaneous interaction of the cationic polymer and nucleic acid molecules with negative electricity. The preparation method is simple process; and the photoactive nano composite can be used as a photoswitch and also can be used as a photosensitizer, and has a wide prospect in the field of guiding disease diagnosis and treatment and photodynamics therapy.

Light-responsive amphiphilic copolymer coated nanoparticles as nanocarriers and real-time monitors for controlled drug release

Herein, light-responsive nanocarriers based on hollow mesoporous silica (HMS) nanoparticles modified with spiropyran-containing light-responsive copolymer (PRMS-FA) were fabricated via a simple self-assembly process. HMS modified with long-chain hydrocarb