Synthesis and properties of ionic conjugated polymer with spiroxazine moiety

Kim, Sung-Hoon; Lee, Soo-Jong; Park, So‐Yeon; Suh, Hee-Jung; Jin, Sung‐Ho; Gal, Yeong‐Soon

doi:10.1016/j.dyepig.2004.12.017

Cited by 24 publications

(5 citation statements)

References 36 publications

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“…Because the MC form of spirooxazines has a predominant keto-type structure, polymers covalently linked to spirooxazine groups exhibit positive photochromic phenomena, even in water solutions [ 24 ], or when the polymers are polyelectrolytes. [ 74 – 76 ] In contrast with spirooxazines, the MC forms of some special spiropyran compounds, especially those with free nitro, carboxy, or sulfo groups, exhibit negative photochromic phenomena in a strong polar solvent [ 72 , 73 ]. This means that the MC forms of those spiropyran compounds essentially possess a zwitterion-type structure; therefore, the strong polar solvent stabilizes the MC.…”

Section: Resultsmentioning

confidence: 99%

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Sun

Yao

et al. 2020

Designed Monomers and Polymers

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1ʹ-(2-Acryloxyethyl)-3,3ʹ-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2ʹ-indoline] (SPA) was synthesized and grafted onto a water-soluble carboxymethyl chitin (CMCH) macromolecule to prepare a photochromic copolymer (CMCH-g-SPA). The structure of CMCH-g-SPA was characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric (TG) analysis, X-ray diffraction (XRD) analysis, water-solubility evaluation, and UV-vis spectroscopy. XRD patterns of CMCH-g-SPA revealed that grafting copolymerization disrupts the CMCH semicrystalline structure, thus improving water solubility. UV-vis spectroscopy results supported the negative photochromic behavior of the merocyanine (MC) form of CMCH-g-SPA (CMCH-g-MCA) present in a water solution of the target copolymer. In addition to high solvent polarity, the intermolecular and intramolecular electrostatic attraction between the indolenine cation and the COO − anion were found to be influencing factors, which stabilize these MC form of spiropyran groups grafted onto CMCH. In a water solution, visible light bleaching was completed over a short period (8 minutes) under artificial visible light irradiation and the thermal coloration reaction, whose rate constant at 25 °C was 4.64 × 10 −4 s −1 , which fit the first-order reaction equation. After ten photochromic cycles in water solution, the relative absorption intensity of CMCH-g-MCA decreased by 7.92%.

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Section: Resultsmentioning

confidence: 99%

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Sun

Yao

et al. 2020

Designed Monomers and Polymers

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“…In recent years, photochromic materials have been widely applied in protective ophthalmic lenses, security printing, optical memory and switching, solar energy storage and electrophoretic displays [1,2] because they can change from colorless to colorful when exposed to UV light but can become colorless again after the UV light is removed [2][3][4][5]. Among photochromic materials, spirooxazines have received considerable attention due to their intense photocoloration [6][7][8], fatigue resistance and ease of synthesis [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Fabrication and Characterization of Photochromic Spirooxazine/Polyvinylidene Fluoride Fiber Membranes via Electrospinning

Peng

Guo

Lan

et al. 2018

Fibres and Textiles in Eastern Europe

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In this study, photochromic spirooxazine material of N-methyl-3,3-dimethyl-9’-hydroxy-spiro [2H-indole-2-[3H] naphtho [2,1-b] [1,4] oxazine] was synthesised. Spirooxazine/PVDF fiber (SPF) membranes with different contents of spirooxazine were successfully prepared by electrospinning. The SPF membranes were characterised by FTIR and SEM. The photochromic properties and contact angle of the SPF membranes were evaluated. The results show that the SPF membranes change from colorless to blue when exposed to UV light, but they revert to their original colour after the UV light disappears. The colour difference and contact angle of the SPF membranes firstly increase and then decrease with a rise in the content of spirooxazine.

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“…Photochromism studies of spirooxazine in polymer matrices [17], liquid crystal polymers containing spirooxazine as mesophases [18], spirooxazine grafted, poly[2-ethynyl-pyridinum bromide] ionic conjugated polymer [19], poly[N,N- [20] and other synthetic polymers [21,22] have recently been developed. However, photocontrollable fluorescent changes of spirooxazine are very scarce [23]; in particular, photoswitchable fluorescent photochromic spirooxazine polymers are virtually unknown.…”

Section: Introductionmentioning

confidence: 99%