Synthesis and photochromic properties of naphthopyran polymer containing photocrosslinkable coumarin moiety

Xie, Bijun; Wang, Guang; Zhao, Xiancai

doi:10.1002/app.34427

Cited by 10 publications

(4 citation statements)

References 49 publications

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“…UV irradiation of these uncolored molecules leads to the formation of highly conjugated colored species that, in the absence of light, return thermally, with variable speed, to the closed form . The phenomen occurs in solution or when the molecules are dispersed in polymeric matrices, although the kinetics of the process is highly affected by the nature of the host matrix. − The relative ease of chemical synthesis, the versatility of the photochromic activity, the thermal stability, and the notable fatigue resistance made these compounds the most commercially important class of photochromic molecules used for the production of photochromic plastic ophthalmic lenses that show a rapid and reversible color change at room temperature when exposed to the sunlight. − …”

Section: Introductionmentioning

confidence: 99%

Photochromic Fused-Naphthopyrans without Residual Color

et al. 2012

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A series of new photochromic fused-naphthopyrans with an alkyl bridge between the pyran ring and the naphthalenic core was synthesized in several steps from 4-(bromomethyl)benzocoumarin. The presence of the alkyl bridge in these new fused-naphthopyrans prevents the formation of one long-lived photoisomer and therefore has a dramatic effect on their photochromic properties: UV irradiation of common naphthopyrans gives rise to two isomeric colored photoisomers, one of which fades very slowly and is responsible for a persistent residual color. UV excitation of these new uncolored fused-naphthopyrans leads to the formation of only one colored photoisomer that fades completely to the uncolored state in few seconds/minutes following a monoexponential decay law, thus avoiding the problem of the residual coloration typically observed with naphthopyrans.

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Section: Introductionmentioning

confidence: 99%

Photochromic Fused-Naphthopyrans without Residual Color

et al. 2012

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“…In addition, Wang et al demonstrated a reduced decoloration of a copolymer bearing naphthopyran and Cou7 moieties in the side-chains due to the preferred dimerization of the coumarin in comparison to the photoinduced ring-opening of the naphthopyran. 164 The copolymers were obtained by ATRP using CuBr complexed with PMDETA as catalyst and ethyl-bromoisobutylate as initiator. In contrast, a living cationic polymerization of Cou8 was reported by Minoda and coworkers.…”

Section: Coumarinsmentioning

confidence: 99%

Fluorescent monomers as building blocks for dye labeled polymers: synthesis and application in energy conversion, biolabeling and sensors

2013

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This review focuses on side-chain functionalized polymers derived from direct (co)polymerization of fluorescent dyes. This overview about polymerizable dyes includes 1,8-naphthalimides, fluoresceins, rhodamines, coumarins, azo-dyes, oxadiazoles, diverse aromatic dyes as well as selected other dyes that cannot be classified within these groups. The discussed dyes have been functionalized with a polymerizable unit in order to apply straight-forward polymerization procedures. Therefore, the center of attention is set to the optical properties of the polymerizable dyes and the applicable polymerization techniques. Furthermore, the various applications (i.e., in biomedicine and pharmacy, as thermo-responsive materials and energy transfer materials, for dispersion of carbon nanotubes and others) of each polymer are discussed.

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“…Previous studies showed that the molecular structure and properties of the medium in which photochromic dyes are dispersed play a very important role with respect to the photochromic performance of these dyes . Properties of the medium such as chain stiffness, viscosity, polarity, and fractional free volume affect the photochromic activity by, for example, constraining the rotational mobility of the dyes.…”

Section: Introductionmentioning

confidence: 99%

The effect of molecular structure on the secondary transitions and their influence on the decoloration kinetics of photochromic dyes in co‐polycarbonates

Micciché

Ramakrishnan

Hoeks

2016

J Polym Sci B Polym Phys

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Photochromic dyes have restricted use in rigid polycarbonates because of slow coloration and decoloration kinetics. In this study, it is shown that the decoloration kinetics of two photochromic dyes can be controlled by tuning the chain stiffness and free volume of the host matrix. The introduction of flexible moieties in rigid BPA-based polycarbonate chain accelerates the decoloration of these dyes whereas a rigid comonomer delays the decoloration kinetics. Although T g might be used as a parameter to improve photochromism in polymer matrices, dynamic mechanical analysis demonstrates that the decoloration kinetics of the dyes in host polymer matrices having similar T g depends primarily on the secondary relaxations and, thus, on the polymer architecture. The effect of the comonomer type on the characteristic ratio is also discussed underlining the potential relationship between the free volume and chain stiffness. These results open the possibility to develop transparent or semitransparent photochromic materials based on tailor-made co-polycarbonates.

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Synthesis and photochromic properties of naphthopyran polymer containing photocrosslinkable coumarin moiety

Cited by 10 publications

References 49 publications

Photochromic Fused-Naphthopyrans without Residual Color

Photochromic Fused-Naphthopyrans without Residual Color

Fluorescent monomers as building blocks for dye labeled polymers: synthesis and application in energy conversion, biolabeling and sensors

The effect of molecular structure on the secondary transitions and their influence on the decoloration kinetics of photochromic dyes in co‐polycarbonates

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