Synthesis and Photochromic Properties of Poly(4-vinylpyridine-co-styrene) with Pendant Spiroxazine Moieties

2008 ◽  
Vol 8 (9) ◽  
pp. 4885-4888
Author(s):  
Yeong-Soon Gal ◽  
Won-Chul Lee ◽  
Won Seok Lyoo ◽  
Sung-Ho Jin ◽  
Kwon Taek Lim ◽  
...  
Keyword(s):  
Uv Irradiation ◽  
Ring Closure ◽  
Visible Range ◽  
Merocyanine Form ◽  
Colored Form ◽  
Photochromic Properties ◽  
Ionic Polymer ◽  
Absorbance Changes ◽  
Spiro Form ◽  
Photochromic Reaction

An ionic polymer with pendant photochromic moieties was prepared by the reaction of poly(4-vinylpyridine-co-styrene) and 1,3,3-trimethyl-6′-bromohexyloxyspiro[2H]-indol-2,3′-[3H]-naphth[2,1-b][1,4]oxazine. The photochromic reaction in question is caused by the reversible heterolytic cleavage of the C(spiro)—O bond under UV irradiation, yielding the colored form that can return to the colorless form by ring closure under visible light irradiation or in dark. The visible range absorption of the corresponding polymer increased gradually by UV irradiation which is ascribed to the generation of the open merocyanine form from the closed spiro form. The ionic conductivity of polymer increased upon UV irradiation, which brought about the generation of zwitterions form, and subsequently decreased in dark, which brought about the generation of closed spiro form. Sufficient reversibility was found in this polymer and this response was completely synchronized with that in the absorbance changes.

Light-induced change of the molecular charge in a spironaphthoxazine compound

1993 ◽  
Vol 71 (11) ◽  
pp. 1828-1833 ◽  
Author(s):  
Paul Rys ◽  
Ruth Weber ◽  
Qinglan Wu
Keyword(s):  
Flash Photolysis ◽  
Ph Value ◽  
Uv Light ◽  
Merocyanine Form ◽  
Acid Base ◽  
Experimental Conditions ◽  
Base Equilibrium ◽  
Acid Base Equilibrium ◽  
Molecular Charge ◽  
Spiro Form

To evaluate the experimental conditions for the light-induced change of the molecular charge, the dependence of the photochromic reaction behaviour of the indolino spiro naphthoxazine compound 1,3,3-trimethyl-spiro[2H-indol 2,3′-[3H]naphth[2,1-b]-[1,4]oxazine] on the pH value of the solution is investigated. In the absence of UV light an acid–base equilibrium between the spiro form and a protonated closed form is established. By irradiation under appropriate acidic conditions the spiro form can be transformed into an open cationic form through the merocyanine form. Between the two open forms an acid–base equilibrium is established. Except for the closed protonated form the structures are confirmed by mean of NMR. The kinetics of the thermal ring-closing reaction of both forms are investigated by flash photolysis. It is shown that the ring-closing reaction proceeds exclusively via the merocyanine form. The pK values determined for both equilibria give the pH range, in which the light-induced change of the molecular charge occurs.

Functionalization of Cellulose Paper by Coating Nano Metal-Organic Frameworks for Use as Photochromic Material

2021 ◽  
Vol 43 (1) ◽  
pp. 67-67
Author(s):  
Qiang Yang Qiang Yang ◽  
Wei Gong Wei Gong ◽  
Xiaowei Cui Xiaowei Cui ◽  
Chunsheng Zhou Chunsheng Zhou
Keyword(s):  
Functional Materials ◽  
Photochromic Properties ◽  
Coated Paper ◽  
Cellulose Paper ◽  
Chemical Structures ◽  
Coating Method ◽  
Potential Applications ◽  
Metal Organic ◽  
Light Green ◽  
Photochromic Reaction

The cellulose paper-based functional materials modified by Zn-NDI and Cu-NDI were prepared by the coating method. The chemical structures were characterized by FTIR, XRD, UV-vis and SEM, and the photochromic properties of the composite functional materials were studied. The results showed that Zn-NDI and Cu-NDI were successfully prepared and retained on the surface of copy paper, the wavelength of photochromic reaction is between 300-400 nm of MOFs materials. Optical analysis confirmed that the NDI/paper, Zn-NDI/paper and Cu-NDI/paper changed from tan to wheat, light green to olive, and dark tan to brown after 60 seconds of exposure to hernia light irradiations, the MOFs coated paper returned to its original color when it was placed in the dark for 4 hours. The above results indicated that the prepared Zn-NDI and Cu-NDI coated paper composites exhibited excellent photochromic ability and had potential applications in the field of anti-counterfeiting packaging materials.

scholarly journals Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

2019 ◽  
Vol 15 ◽  
pp. 2133-2141 ◽  
Author(s):  
Marco Santella ◽  
Eduardo Della Pia ◽  
Jakob Kryger Sørensen ◽  
Bo W Laursen
Keyword(s):  
Optical Properties ◽  
Nucleophilic Substitution ◽  
Ring Closure ◽  
Visible Range ◽  
Aromatic Nucleophilic Substitution ◽  
Methoxy Groups

Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φf = 0.1 to Φf = 0.3).

Synthesis, Properties and Application in Optical Memory of a Novel Photochromic Diarylethene Bearing an Anthracene Ring

2011 ◽  
Vol 399-401 ◽  
pp. 1055-1058
Author(s):  
Shang Hua He ◽  
Gang Liu ◽  
Shi Qiang Cui
Keyword(s):  
Optical Memory ◽  
Order Reaction ◽  
Photochromic Properties ◽  
Strong Fluorescence ◽  
First Order ◽  
Cyclization Process ◽  
Open Ring ◽  
Synthesis Properties ◽  
Photochromic Reaction ◽  
Hexane Solution

In the present study, we designed a novel unsymmetrical isomeric diarylethene derivative bearing both thiophene and anthracene moieties. Its photochromic properties and fluorescence were investigated in detail. In hexane solution, the open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence. The photochromic reaction kinetics indicated that the cyclization process of 1o belongs to the zeroth order reaction and the cycloreversion process belongs to the first order reaction. This new photochromic system also exhibited remarkable optical storage character.

scholarly journals Preparation and Photochromic Performance of Homogeneous Phase Nitrocellulose Membrane Grafting Spirooxazine Moieties

Coatings ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 569
Author(s):  
Bin-Bin Sun ◽  
Bing-Hua Yao ◽  
Yang-Qing He ◽  
Bo Yang
Keyword(s):  
Ethyl Acetate ◽  
Acetate Solution ◽  
Ethyl Acetate Solution ◽  
Colored Form ◽  
Isobutyl Ketone ◽  
Photochromic Properties ◽  
Photochromic Behavior ◽  
Reaction Rate Constants ◽  
13C Nuclear Magnetic Resonance ◽  
Relative Absorption

The synthesis of 1,3,3-trimethyl-9′-acryloxyspiro[indoline-2,3′(3H)naphtho[2,1-b][l,4]-oxazine] (AISO) was carried out by catalytic esterification of 1,3,3-trimethyl-9′-hydroxyspiro-[indoline-2,3′(3H)naphtho[2,1-b][l,4]oxazine] (SO–OH) and acrylic acid in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and N-dimethylaminopyridine (DMAP). Then, the synthesis of the target copolymer (NC-g-AISO) was was carried out by benzoyl peroxide (BPO)-induced graft copolymerization of the AISO monomer onto nitrocellulose (NC) in a homogeneous methyl isobutyl ketone medium. The structure of NC-g-AISO was characterized by Fourier transform infrared (IR) spectroscopy, 13C Nuclear Magnetic Resonance (NMR) spectra and thermogravimetric (TG) analysis. The photochromic properties of NC-g-AISO were investigated by examining UV–Vis spectra in ethyl acetate solution and solid membrane. Compared with the AISO monomer in ethyl acetate solution, the thermal color decay stability of the colored form of NC-g-AISO in ethyl acetate solution and in solid membrane improved significantly. The thermal color decay reaction rate constants in ethyl acetate solution and membrane at 25 °C were 1.77 × 10–2 and 1.36 × 10–3 s–1, respectively, fitted using the first-order reaction equation. After ten photochromic cycles, the relative absorption intensity of the colored form of NC-g-AISO decreased by 0.85%, indicating that the NC-g-AISO membrane has good reversible photochromic behavior.

Theoretical investigation on a series of novel S,S-dioxide diarylethenes with abnormal photochromic properties and design of new dyads

2015 ◽  
Vol 39 (3) ◽  
pp. 1634-1642 ◽  
Author(s):  
Zhi-Xiang Zhang ◽  
Fu-Quan Bai ◽  
Li Li ◽  
Hong-Xing Zhang
Keyword(s):  
Theoretical Investigation ◽  
Conjugation System ◽  
Photochromic Properties ◽  
Photochromic Reaction

A novel diarylethene shows an abnormal conjugation system switch in a photochromic reaction, according to which new dyads were designed.

Functionalization of Cellulose Paper by Coating Nano Metal-Organic Frameworks for Use as Photochromic Material

2021 ◽  
Vol 43 (1) ◽  
pp. 67-67
Author(s):  
Qiang Yang Qiang Yang ◽  
Wei Gong Wei Gong ◽  
Xiaowei Cui Xiaowei Cui ◽  
Chunsheng Zhou Chunsheng Zhou
Keyword(s):  
Functional Materials ◽  
Photochromic Properties ◽  
Coated Paper ◽  
Cellulose Paper ◽  
Chemical Structures ◽  
Coating Method ◽  
Potential Applications ◽  
Metal Organic ◽  
Light Green ◽  
Photochromic Reaction

The cellulose paper-based functional materials modified by Zn-NDI and Cu-NDI were prepared by the coating method. The chemical structures were characterized by FTIR, XRD, UV-vis and SEM, and the photochromic properties of the composite functional materials were studied. The results showed that Zn-NDI and Cu-NDI were successfully prepared and retained on the surface of copy paper, the wavelength of photochromic reaction is between 300-400 nm of MOFs materials. Optical analysis confirmed that the NDI/paper, Zn-NDI/paper and Cu-NDI/paper changed from tan to wheat, light green to olive, and dark tan to brown after 60 seconds of exposure to hernia light irradiations, the MOFs coated paper returned to its original color when it was placed in the dark for 4 hours. The above results indicated that the prepared Zn-NDI and Cu-NDI coated paper composites exhibited excellent photochromic ability and had potential applications in the field of anti-counterfeiting packaging materials.

Functionalization of Cellulose Paper by Coating Nano Metal-Organic Frameworks for Use as Photochromic Material

2021 ◽  
Vol 43 (1) ◽  
pp. 67-67
Author(s):  
Qiang Yang Qiang Yang ◽  
Wei Gong Wei Gong ◽  
Xiaowei Cui Xiaowei Cui ◽  
Chunsheng Zhou Chunsheng Zhou
Keyword(s):  
Functional Materials ◽  
Photochromic Properties ◽  
Coated Paper ◽  
Cellulose Paper ◽  
Chemical Structures ◽  
Coating Method ◽  
Potential Applications ◽  
Metal Organic ◽  
Light Green ◽  
Photochromic Reaction

The cellulose paper-based functional materials modified by Zn-NDI and Cu-NDI were prepared by the coating method. The chemical structures were characterized by FTIR, XRD, UV-vis and SEM, and the photochromic properties of the composite functional materials were studied. The results showed that Zn-NDI and Cu-NDI were successfully prepared and retained on the surface of copy paper, the wavelength of photochromic reaction is between 300-400 nm of MOFs materials. Optical analysis confirmed that the NDI/paper, Zn-NDI/paper and Cu-NDI/paper changed from tan to wheat, light green to olive, and dark tan to brown after 60 seconds of exposure to hernia light irradiations, the MOFs coated paper returned to its original color when it was placed in the dark for 4 hours. The above results indicated that the prepared Zn-NDI and Cu-NDI coated paper composites exhibited excellent photochromic ability and had potential applications in the field of anti-counterfeiting packaging materials.

scholarly journals 5-Ureido-3,3-diphenyl-3H-naphtho[2,1-b]pyrans: Photoswitchable self-assembling architectures

2004 ◽  
Vol 6 (4) ◽  
pp. 169-173 ◽  
Author(s):  
X. Sallenave ◽  
S. Delbaere ◽  
S. Ahmed ◽  
G. Vermeersch ◽  
J. L. Pozzo
Keyword(s):  
Carbonyl Group ◽  
Uv Irradiation ◽  
2D Nmr ◽  
Intramolecular Interactions ◽  
The Self ◽  
Visible Spectroscopy ◽  
Photochromic Properties ◽  
Self Assembling ◽  
Amino Derivatives ◽  
Uv Visible

5-Ureido-3,3-diphenyl-3H-naphtho[2,1-b]pyrans have been synthesized and their photochromic properties have been quantified using UV-Visible spectroscopy. The urea pattern is responsive for the selfassembling properties under both colourless and coloured forms whereas the corresponding amino derivatives do not show any aggregative properties. The geometries of the different states have been assigned using1Hand19FNMR spectroscopies, and thereafter their respective kind of aggregates could be proposed through the different inter- and intramolecular interactions. Upon UV irradiation, the pyranic ring is opened and the resulting photogenerated carbonyl group is competing with the urea in the self-assembling process and consequently strongly affects the supramolecular assemblies. The inter- and intramolecular contributions have been quantified through 1D and 2D NMR experiments along with the variation in the concentration.

Synthesis of a New Photochromic Compound for Optical Storage

2010 ◽  
Vol 156-157 ◽  
pp. 462-466
Author(s):  
Shi Qiang Cui ◽  
Shou Zhi Pu ◽  
Gang Liu ◽  
Wei Jun Liu
Keyword(s):  
Reaction Kinetics ◽  
Uv Light ◽  
Optical Storage ◽  
Order Reaction ◽  
Pmma Film ◽  
Zeroth Order ◽  
Photochromic Compound ◽  
Photochromic Properties ◽  
First Order ◽  
Photochromic Reaction

A new photochromic compound 1-[2,5-dimethyl-3-thienyl]-2-[2-methyl-5-pyridine-3-yl-3-thieyl] perfluoroyclopentene(1a) was synthesized, its photochromic properties were examined, the result indicated that the color of the compound 1a changed from colorless to a purple one upon irradiation with 297 nm UV light, a new absorption maxima were observed at 549 and 553 nm in hexane and PMMA film, respectively. The the photochromic reaction kinetics indicated that the cyclization processes of 1 belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction.This new photochromic system also exhibited remarkable optical storage character.

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