Peculiarities of photochromic behaviour of spiropyrans and spirooxazines

Marevtsev, V. S.; Zaichenko, N. L.

doi:10.1016/s1010-6030(96)04566-2

Cited by 33 publications

(27 citation statements)

References 15 publications

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“…We examined 1`,3`3`-trimethylspiro[indoline-2,2`-2H-naphtho [2,1-b] [1,4]oxazine, mp 124 3125oC, R f = 0.93 (benzene : ether, 7 : 3, Silufol); l max 300 and 320 nm (dioxane, e = 9.75 0 10 35 l mol 31 cm 31 ); 1H NMR spectra (C 6 …”

Section: Methodsmentioning

confidence: 99%

Coloration of Spirooxazine in Various Organic Matrices under Plastic Flow at High Pressure

et al. 2005

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The behavior of 1,3,3-trimethylspiro[indoline-2,3`-2H-naphtho[2,1-b][1,4]oxazine under plastic deformation was studied on high-pressure Bridgman anvil-type apparatus at 0.53 4 GPa and room temperature.High pressures strongly modify various solids, e.g., cause an insulator3conductor transition, unusual chemical processes, changes in phase diagrams, etc. Substances subjected to high pressures are often exposed to shear stresses responsible for plastic deformations substantially affecting their behavior. A combined effect of high pressures and shear deformations on substances is strongly manifested in the case of high-pressure Bridgman anvil-type apparatus. In particular, various chemical reactions were revealed in the absence of initiators and catalysts for many classes of organic compounds. This suggests an electronic excitation of substances under such impacts. The rate of chemical processes under plastic deformations at high pressures is very weakly dependent on temperature, which supports the athermal mechanism of excitation of chemical transformations.In the context of studying the excitation mechanisms of the electronic subsystem of solids under mechanical impacts, of much interest are organic reactions that can be photochemically initiated under ordinary conditions. For such systems, the positions of the ground and excited levels of the reacting molecules, the transition energies, and transformation pathways of the excited states are well understood. We have applied such an approach to a study of the behavior of linear annelated aromatic compounds [1]. It was shown that, under plastic deformation at high pressures, only 20% of the energy required for a chemical reaction to occur in the substances under study is due to high pressures, and the remainder comes from plastic deformation. In [2], we analyzed the baric dependences of a purely mechanical characteristic of solids (flow stress) for a wide variety of organic compounds and found that such dependences can be correlated with the processes occurring in the electronic subsystem of organic substances.Another class of organic compounds whose photochemical transformations in solutions and polymer films are well understood are photochromes and, in particular, spiropyrans and spirooxazines [3 3 6]. Under photoirradiation in solution, they acquire a predominantly dark blue color (l max~6 00 nm and over) owing to a transition of the molecule from a colorless initial state A with opening of the spiro bond into a colored merocyanine form B:

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Section: Methodsmentioning

confidence: 99%

Coloration of Spirooxazine in Various Organic Matrices under Plastic Flow at High Pressure

et al. 2005

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“…The properties of spironaphthoxazines and their derivatives have been reported in detail previously 34, 35, 38–48. The swelling properties of hydrogels having spironaphthoxazine moieties as pendant groups following treatment with light and heat have not been reported.…”

Section: Introductionmentioning

confidence: 99%

“…Many photochromic functionalities have been used including triphenylmethane leuco dye derivatives, modified azobenzenes, and spirobenzopyran derivatives 2, 6, 7, 20, 32, 33. Among a plethora of photochromic compounds, spironaphthoxazines are of particular value because of their resistance to photo‐fatigue and excellent coloring power 34–37. The spiro pyranyl CO bond dissociates following absorption of UV radiation, converting from its colorless closed form 1 into the highly blue colored open merocyanine form 2 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Dual responsive poly(N‐isopropylacrylamide) hydrogels having spironaphthoxazines as pendant groups

Kulawardana

Kuruwita-Mudiyanselage

Neckers

2009

J. Polym. Sci. A Polym. Chem.

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Stimuli responsive hydrogels (PNIPAAm‐MSp) with a thermoresponsive backbone and photochromic pendant groups were synthesized via free radical polymerization using N‐isopropylacrylamide, modified spironaphthoxazines with a polymerizable double bond (MSp) as photochromic monomer, the crosslinker N,N′‐methylenebis(acrylamide) and the initiator 2,2′‐azobis(isobutyronitrile) in dimethylsulfoxide. The polymers are dual responsive, in that poly(N‐isopropylacrylamide) (PNIPAAm) responds to temperature changes whereas the pendant spironaphthoxazines respond to light. Irradiation enhanced the water absorption of the polymers while increases in temperature decreased it. The irradiated PNIPAAm‐MSp showed best water absorption at 0 °C (Q = 3.25) while water desorbed at higher temperatures (35 °C; Q = 0.30); where Q is the amount of water absorbed by a gram of dry polymer. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3318–3325, 2009

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“…The photoresponsive site of the SPO comes from the center sp 3 spiro carbon. Upon UV irradiation, the carbonoxygen bond cleaves and achieves sp 2 hybridization, yielding an open planar merocyanine (MC), which is metastable and readily isomerizes [11,12]. So it can revert back to the spiro form via ring closing when irradiated with visible light or thermal radiation.…”

Section: Introductionmentioning

confidence: 99%

A Photochromic Copolymer Hydrogel Contact Lens: From Synthesis to Application

Yang

Huang

Zhou

et al. 2016

International Journal of Polymer Science

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A photochromic poly(2-hydroxyl-ethyl methacrylate-N-vinylpyrrolidone-spironaphthoxazine) hydrogel (p(HEMA-NVP-SPO)) has been designed and synthesized by free radical polymerization in this work. The chemical and structural information of hydrogels was investigated by IR spectra, equilibrium water content (EWC), and SEM. The IR spectra confirmed successful synthesis of copolymer. The domain of NVP contributed to not only EWC but also inner structure of hydrogel, while SPO had little influence on these properties of hydrogel. The photochromic behaviors of hydrogel including photochromic properties and thermal fading kinetics were systematically studied and compared with hydrogel made by immersing method. Results showed that when SPO was incorporated in hydrogel by polymerization, maximum absorbance wavelength got shorter, and the relaxation half-life became longer. In addition, salicylic acid as a drug model could be loaded into hydrogel by immersing method, and its sustained drug release in a given period was dependent on the characteristics of solution and loading time.

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Peculiarities of photochromic behaviour of spiropyrans and spirooxazines

Cited by 33 publications

References 15 publications

Coloration of Spirooxazine in Various Organic Matrices under Plastic Flow at High Pressure

Coloration of Spirooxazine in Various Organic Matrices under Plastic Flow at High Pressure

Dual responsive poly(N‐isopropylacrylamide) hydrogels having spironaphthoxazines as pendant groups

A Photochromic Copolymer Hydrogel Contact Lens: From Synthesis to Application

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