Photochromic cross-linked copolymer containing thermally stable fluorescing 2-indolylfulgimide

Liang, Yongchao; Dvornikov, Alexander; Rentzepis, P. M.

doi:10.1039/b002335n

Cited by 16 publications

(9 citation statements)

References 7 publications

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“…Rentzepis et al reported photochromic linear and cross-linked copolymers of methyl methacrylate and 2-indolylfulgimides with pendant vinyl benzenes [17,18]. These copolymers had similar properties as the corresponding monomeric 2-indolylfulgimides.…”

Section: Introductionmentioning

confidence: 99%

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Islamova

Chen

Fan

et al. 2013

Polymer Degradation and Stability

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Photochromic indolylfulgimides covalently attached to polymers have beneficial properties for optical switching. A 3-indolylfulgide and two 3-indolylfulgimides with one or two polymerizable styrene groups attached on the nitrogen atom(s) were synthesized. Copolymerization with methyl methacrylate (MMA) provided linear copolymers (one styrene group) or a cross-linked copolymer (two styrene groups). The properties of the monomers and copolymers in toluene or as thin films were characterized. The new copolymers were photochromic (reversible Z-to-C isomerization), absorbed visible light, and revealed good thermal and photochemical stability. At room temperature, all copolymer films showed no loss of absorbance after 5 weeks. At 80 °C in either toluene or as films, the Z-forms copolymers were less stable than the C-form copolymers, which showed little or no degradation after 400 h. The degradation rate due to repeated ring-closing – ring opening cycles was less than 3% per 100 cycles. The cross-linked copolymer showed photochemical stability comparable to monomeric fulgides in toluene, <1% per 100 cycles. In general, the properties of the linear and cross-linked copolymers were similar to the corresponding monomers in toluene. In films, the conformations of the Z-form were restricted due to the matrix indicating that the preparation of films from the C-form is advantageous.

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Section: Introductionmentioning

confidence: 99%

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Islamova

Chen

Fan

et al. 2013

Polymer Degradation and Stability

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“…Concentrations of 10 −1 M and higher are needed for the device to perform at the required writing and reading efficiencies 13. To achieve the high concentrations of photochromism in the polymer matrix, Rentzepis and coworkers14 synthesized photochromic crosslinked copolymers by attaching the photochromic fulgimide molecules to the polymer chain and copolymerizing it with methyl methacrylate and characterizing their switching properties. Cu (I)‐catalyzed ligation of organic azides and terminal alkynes belong to a group of reactions referred as “Click Chemistry,” a term coined by Huisgen et al15 These compounds are well known for their biological properties such as antiallergic,16 antiviral applications and also in materials chemistry 17.…”

Section: Introductionmentioning

confidence: 99%

Optical switching, photophysical, and electrochemical behaviors of pendant triazole‐linked indolylfulgimide polymer

Nithyanandan

Kannan

Karuppannan

et al. 2011

J. Polym. Sci. A Polym. Chem.

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Triazole-linked 2-indolylfulgimide polymer has been synthesized and its photochromic switching behavior has been characterized by NMR, IR, GPC, TGA, DSC, and UV-Vis spectroscopy. The synthesized photochromic polymer showed absorption peak maxima at 386 and 510 nm wherein the absorption at 510 nm was attributed to charge transfer from triazole ring nitrogen to carbonyl carbon of fulgimide unit. Fluorescence lifetime studies on exciting at 550 nm reveals triexponential behavior with fluorescence decay around 0.1, 1 and 4.2 ns, which correspond to open (E), closed (C) form of fulgimide and triazole ring, respectively. Whereas exciting at 470 nm evidences biexponential fit with fluorescence decay around 0.1 and 2.2 ns, which corresponds to the closed (C) form and triazole ring, respectively. Fluorescence decay of tria-zole ring was found to be influenced by the excitation wavelength. The cyclic voltammogram of open form of polymer depicts irreversible reductive wave at À1.4 V. On illumination with 360-nm light, the reduction wave of polymer was shifted toward less cathodic wave at À0.9 V; this leads to formation of the closed form of fulgimide unit. V

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“…Most of the optoelectronic devices, for example 3D optical memory devices, demand photochromic material at higher concentrations and in the robust medium such as beads, films and moldable materials.. 41 Rentzepis et al 42,43…”

Section: Synthesis Of Copolymer Containing Fulgide or Fulgimidementioning

confidence: 99%

Synthesis and Characterization of a Hydrolytically Stable Photochromic Copolymer Containing an N-alkylindolylfulgimide

yasmeen¹

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Fulgides and fulgimides comprise one class of thermally irreversible photochromic organic compounds. Light dependent isomerization, has made these organic molecules promising materials for several applications, including optical memory devices, and switches. Hydrolytic stability of fulgides and fulgimides is crucial for their practical applications in biological systems and humid environments. Fulgimides, the most important derivative of fulgides, have a succinimide ring, which, unlike the anhydride ring, of fulgides, is resistant to hydrolytic degradation. A novel N-alkylindolylfulgimide was synthesized and copolymerized with acrylamide. The photochromic and hydrolytic properties of the copolymer in phosphate (pH 7.4) and acetate (pH 5.0) buffer solutions were characterized. The N-alkylindolylfulgimide based copolymer exhibited significantly enhanced hydrolytic stability (50 times better in phosphate buffer) and similar photochromic properties as a copolymer containing an N-arylindolylfulgimide. vii

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Photochromic cross-linked copolymer containing thermally stable fluorescing 2-indolylfulgimide

Cited by 16 publications

References 7 publications

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Optical switching, photophysical, and electrochemical behaviors of pendant triazole‐linked indolylfulgimide polymer

Synthesis and Characterization of a Hydrolytically Stable Photochromic Copolymer Containing an N-alkylindolylfulgimide

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