A New Photochromic Spiro[3<i>H</i>-1,4-oxazine]

Kawauchi, Susumu; Yoshida, Haruo; Yamashina, Naoko; Ohira, Manabu; Saeda, Shigeru; Irie, Masahiro

doi:10.1246/bcsj.63.267

Cited by 60 publications

(13 citation statements)

References 3 publications

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“…Here, we describe the design of a nonwhite cool material that can be intelligently temperature regulated, where indolinospirooxazine (NISO) is incorporated onto ethylene‐vinyl acetate copolymer (EVA). As a class of photosensitive color‐changing compounds, NISO has a variety of colors, good reversibility, excellent fatigue resistance, and the ability to regulate color according to the intensity of sunlight . Besides, most of photochromic materials on the market are currently applied for anticounterfeiting or decoration, while some are applied to block sunlight with discoloration such as color‐changing sunglasses .…”

Section: Introductionmentioning

confidence: 99%

Incorporation of indolinospirooxazine on ethylene‐vinyl acetate copolymer to produce a intelligently temperature‐regulated nonwhite cool material

Zhang

2019

J of Applied Polymer Sci

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Cool materials that adjust cooling efficiency according to sunlight intensity are needed because people have different needs for cooling at different times. Several colors of commercial microencapsulated photochromic powder were melt blended with ethylene-vinyl acetate copolymer in a two-roll mill at 90 C to prepare the photochromic films of corresponding colors. Pink photochromic films [the organic photochromic compound is indolinospirooxazine (NISO)] were selected to continue the following variable experiment due to its best performance in the indoor cooling test. The pink photochromic films change color as well as transmittance according to the intensity of sunlight, thereby achieving an intelligent cooling effect. A maximum decrease around 10 C was observed in natural environment when the addition amount of pink photochromic powder reaches 2.0 phr under strong sunlight and all films did not show cooling effect under weak sunlight. This material can be covered on buildings to regulate the indoor temperature.

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Section: Introductionmentioning

confidence: 99%

Incorporation of indolinospirooxazine on ethylene‐vinyl acetate copolymer to produce a intelligently temperature‐regulated nonwhite cool material

Zhang

2019

J of Applied Polymer Sci

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“…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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“…(Fig. 1) Due to the easy light fatigue of spirobenzopyrans (SP) [23], our studies were extended to spironaphthoxazines (NO) [8,23] and naphthopyrans (chromens, NP) [24,25] because of their greater resistence to photodegradation. The UV light induced ring opening of the colorless NO and NP photochromes is similar to that of SP (C -O cleveage), but here quinoidal and not zwitterionic structure of the open forms is responsible for the coloration [26,27] (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…In contrast, crowned NP molecules were published to resist to alkali cation-facilitated thermal isomerization, while Ca 2þ and Mg 2þ induce moderate coloration. Upon UV irradiation, however, the opening of the pyran ring of NP dyes was markedly facilitated by alkali-and alkaline earth metal cations as well [23,24]. Consequently, the crowned SP, NO and NP molecules are regarded as special chromogenic receptors of dual character.…”

Section: Introductionmentioning

confidence: 99%

1,1'-Binaphtho(aza)crowns Carrying Photochromic Signalling Unit, I: Synthesis, Characterization and Cation Recognition Properties

Kőszegi

Grűn

Bitter

2006

Supramolecular Chemistry

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S)-1,1'-Binaphtho(monoaza)crown-5,-6 and-7 ionophores carrying photochromic indolospirobenzopyran (SP), naphthoxazine (NO) and naphthopyran (NP) signalling groups were synthesized and their cationinduced isomerisation to the colored merocyanine or quinone forms was studied by UV/Vis spectroscopy in the presence of alkali and alkaline earth metal ions. Under dark conditions the equilibrium of SP and NO dyes were remarkably shifted to the colored form by cations of high positive charge density (Li 1 and alkaline earth metal ions). The same effects were observed with crowned NPs after UV irradiation. The stability of some merocyanine-cation complexes were evaluated by calculating the kinetic parameters of the coloration process.

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A New Photochromic Spiro[3H-1,4-oxazine]

Cited by 60 publications

References 3 publications

Incorporation of indolinospirooxazine on ethylene‐vinyl acetate copolymer to produce a intelligently temperature‐regulated nonwhite cool material

Incorporation of indolinospirooxazine on ethylene‐vinyl acetate copolymer to produce a intelligently temperature‐regulated nonwhite cool material

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

1,1'-Binaphtho(aza)crowns Carrying Photochromic Signalling Unit, I: Synthesis, Characterization and Cation Recognition Properties

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