PHOTOCHROMISM IN SPIROPYRANS. PART IV.<sup>1</sup> EVIDENCE FOR THE EXISTENCE OF SEVERAL FORMS OF THE COLORED MODIFICATION

Heiligman-Rim, Rahel; Hirshberg, Yehuda; Fischer, Ernst Otto

doi:10.1021/j100818a035

Cited by 119 publications

(40 citation statements)

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“…8, where the authors showed that in viscous solutions several MC forms can exist and transform into each other upon photoexcitation or thermal treatment. In our case, the conformers are most characteristic in the luminescence spectra upon photoexcitation at different wavelengths (Fig.…”

Section: Resultsmentioning

confidence: 99%

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

et al. 2006

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1´,3´,3´ Trimethyl 6 nitro 8 pyridiniomethylspiro[2H [1]benzopyran 2,2´ indoline] chlo ride (1) was synthesized. Single crystals (crystal hydrates) of the open merocyanine form of compound 1 were obtained under the dark conditions, and their crystal structure was studied. On irradiation with visible light compound 1 crystallizes from propan 2 ol in the polycrystal line closed form. The spectral and photochemical properties of compound 1 in the polycrystal line state and the kinetic characteristics on thermal transformation of the closed form to the open form were studied.Hybrid polyfunctional compounds of a principally new class have recently been synthesized. 1,2 They combine two sublattices in one crystal structure: the photo chromic cationic sublattice of spiropyrans and magnetic anionic sublattice, for instance, of bimetallic oxalate [Cr III Mn II (ох) 3 ] -. Spiropyran (SP) acts as a photochemi cal molecular switcher perturbing the magnetic sublattice. The main problem of design of these polyfunctional com pounds is to collect different functional "building" blocks in one crystal structure retaining specific features of the crystal structures of the blocks, which determine their properties in individual compounds. The design of hybrid materials is also impeded by the fact that the photo chromic transformations of SP require a considerable free volume and, hence, they are hindered in the crystalline state. It has recently been shown 3,4 that the structure of the magnetic anionic sublattice of bimetallic oxalates [M III M II (ох) 3 ] -allows cation size variation to perform in a wide range, and the crystal structure of the spiropyran cation in salts with chloride and iodide anions is found to be favorable for reversible photochromic transformations of spiropyrans. 5,6 These features of the structures of the cationic and anionic sublattices allowed crystal chemical modeling of photochromic ferromagnets to be per formed. 1,2 In this case, it was important that the SP + cation was involved in the reaction in the closed form. Therefore, the equilibrium "closed form of the spiropyran cation SP + open cationic merocyanine form MC + " in solution was shifted to the closed SP form using irra diation with the visible light. No hybrid structure can be obtained from the merocyanine form.In the present work, we repeated the synthesis of pho tochromic 1´,3´,3´ trimethyl 6 nitro 8 pyridiniomethyl spiro[2H [1]benzopyran 2,2´ indoline] chloride (1) con taining the pyridinium fragment in the lateral aliphatic chain and prepared two forms: closed SP form (1a) (poly crystals) and open MC form (1b) (single crystals) as shown Scheme 1

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Section: Resultsmentioning

confidence: 99%

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

et al. 2006

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“…As a result, the structure of MC is formed, leading to intense absorption in the visible spectral region (500−600 nm). [47] 3.4. Circulation of the copolymer P(SPMA-co-DMAEMA) in THF In order to evaluate the cycling performance of the amphiphilic random copolymer, the repeatability of the transformation between SP and MC is investigated by the alternating illumination of UV and visible lights.…”

Section: Kinetics Of Photo-induced Ring-openingmentioning

confidence: 99%

Synthesis of spiropyran-containing random copolymer by atom transfer radical polymerization and its complexation with metal ions

Chen

Liu

Cui

et al. 2015

Designed Monomers and Polymers

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(2015) Synthesis of spiropyran-containing random copolymer by atom transfer radical polymerization and its complexation with metal ions, Designed Monomers and Polymers, 18:6, 574-582, DOI: 10.1080/15685551.2015 An amphiphilic random copolymer containing a monomer 2-(dimethylamino) ethyl methacrylate (DMAEMA) and a light-responsive unit 1′-(2-acryloxyethyl)-3′,3′-dimethyl-6-nitrospiro-(2H-1-benzopyran-2,2′-indoline) (SPMA) was synthesized by atom transfer radical polymerization. The solvatochromic and light responsive behaviors of the resulting P (SPMA-co-DMAEMA) copolymer in solution were investigated by UV-vis absorption spectroscopy. The 'negative' solvatochromism upon the increasing solvents polarity was observed. A strong absorption band was recorded at 589 nm in THF, while the lower values were found at 542 and 520 nm in methanol and water, respectively. Moreover, the random copolymer exhibited a good cycling performance by the alternating illumination with ultraviolet (UV) and visible (Vis) lights. Finally, we studied the complexation of zwitterionic merocyanine (MC) with divalent metal ions, and an obvious shift of the location for the maximum absorption peak was found upon addition of Co 2+ or Mn 2+ . A slight color change of the copolymer solution from blue to purple after complexation with Co 2+ or Mn 2+ was also observed and this phenomenon might provide a potential visual observation for the complexation of P(SPMA-co-DMAEMA) with different metal ions.

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“…Such a device based on two‐photon writing, reading, and erasing in a photochromic dye embedded in a polymer matrix was proposed by Rentzepis . However, the original idea for using spiropyran photochromic dyes for possible data storage purposes had been proposed by Hirshberg . Other two‐photon absorbing dyes also being investigated include fluorescent, fluorene, diarylethene, triphenylamine, and oxazine .…”

Section: Image Storagementioning

confidence: 99%

The role of colorants in the generation, storage, and output of digital still images

Kazlauciunas

2013

Coloration Technology

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The purpose of this review is to highlight the important role that dye and pigment colorants play in the areas of image generation, image storage, and image output with respect to digital still images. Colorants in the form of dyes and pigments play an integral part in the digital still imaging process, from the initial conversion of the original greyscale image into a full‐colour RGB additive image, followed by electronic image storage, and finally to hard‐copy output via non‐impact printing technologies such as inkjet and thermal dye transfer. In addition, both dyes and pigments are also utilised for image generation in the fast‐developing world of electronic paper display technologies. Dyes and pigments were the mainstay of many of the early analogue photographic processes in the areas of image capture and image reproduction, and this review sets out to show that, in the new age of digital imaging, this situation is still prevalent.

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PHOTOCHROMISM IN SPIROPYRANS. PART IV.¹ EVIDENCE FOR THE EXISTENCE OF SEVERAL FORMS OF THE COLORED MODIFICATION

Cited by 119 publications

References 1 publication

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

Synthesis of spiropyran-containing random copolymer by atom transfer radical polymerization and its complexation with metal ions

The role of colorants in the generation, storage, and output of digital still images

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PHOTOCHROMISM IN SPIROPYRANS. PART IV.1 EVIDENCE FOR THE EXISTENCE OF SEVERAL FORMS OF THE COLORED MODIFICATION

Cited by 119 publications

References 1 publication

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

Photo-and thermochromic properties of 1′,3′,3′-trimethyl-6-nitro-8-pyridiniomethylspiro[2H-[1]benzopyran-2,2′-indoline] chloride in the crystalline state

Synthesis of spiropyran-containing random copolymer by atom transfer radical polymerization and its complexation with metal ions

The role of colorants in the generation, storage, and output of digital still images

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PHOTOCHROMISM IN SPIROPYRANS. PART IV.¹ EVIDENCE FOR THE EXISTENCE OF SEVERAL FORMS OF THE COLORED MODIFICATION