Micro-environmental fine-tuning of electronic and kinetic properties of photochromic dyes

Whelan, Jamie; Abdallah, Dalia; Wojtyk, James T. C.; Buncel, Erwin

doi:10.1039/c0jm00585a

Cited by 35 publications

(34 citation statements)

References 114 publications

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“…[25] The MC-to-SP isomerization usually happens spontaneously,a gain followingafirst-order process, and it can be accelerated by visible light. [26] SP cannot transform into MCH + completely,e ven by using an excess amount of acid, so the transformation from SP into MCH + is an equilibrium process. [27] Therefore, the conversion of S1 from the closed-ring form to the open-ring form is usually only partially complete.…”

Section: Resultsmentioning

confidence: 99%

Tunable Morphology of Spiropyran Assemblies: From Nanospheres to Nanorods

Pan

Lü

et al. 2016

Chemistry An Asian Journal

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Spiropyran (SP), which can respond to acid, ultraviolet irradiation, and mechanical force, has received great attention as a classic molecule for the construction of stimuli-responsive materials. However, the self-assembly behavior of SP with a tunable morphology has rarely been investigated. In the present work, a SP derivative bearing two carboxyl groups and one hydroxyl group was prepared and used as a model to investigate the optical properties, molecular self-assembly, and morphology of SP. This pH-responsive derivative could undergo a large morphology variation from a sphere- to a rodlike structure by adjusting the acidity. The indoline and pyridopyran fragments contributed to π-π stacking, whereas the carboxyl groups contributed to hydrogen bonding. Both π-π stacking and hydrogen bonding contributed to the pH-responsive self-assembly. The morphologies of spiropyran aggregates formed under different conditions were characterized by SEM, TEM, and FTIR spectroscopy. Control of the morphology of the spiropyran nanostructure was achieved.

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Section: Resultsmentioning

confidence: 99%

Tunable Morphology of Spiropyran Assemblies: From Nanospheres to Nanorods

Pan

Lü

et al. 2016

Chemistry An Asian Journal

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“…SP-1 is an important model of spiropyran type photochromic compounds [10][11][12][13][14][15][16][17]. Various derivatives of SP-1 have been synthesized that form complexes of high stability with metal ions, like the 'bidentate' ligands (they bridge the metal ion by the phenolic oxygen of their MC form and an additional receptive site) [18,19], the multidentate ligands [20,21] and the spiropyrans with attached macrocyclic coordination spheres [22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Metal complexes of the merocyanine form of nitrobenzospyran: Structure, optical spectra, stability

Kubinyi

Varga

Baranyai

et al. 2011

Journal of Molecular Structure

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“…The transformation of spiropyran into merocyanine can also be induced by pH, solvent polarity, electricity, cations, and mechanical force . This photoisomerization is thermally reversible, and the merocyanine‐spiropyran conversion can be accelerated with visible light (520 nm) . Merocyanine tends to aggregate with other merocyanine and spiropyran molecules .…”

Section: Figurementioning

confidence: 99%

“…[18][19][20][21][22][23][24][25] This photoisomerization is thermally reversible, and the merocyanine-spiropyran conversion can be accelerated with visible light (520 nm). [26] Merocyanine tends to aggregate with other merocyanine and spiropyran molecules. [27,28] Aggregation stabilizes the merocyanine form, and can even prevent spontaneous transformation of merocyanine back to the spiropyran form.…”

Section: Photobreathing Zwitterionic Micellesmentioning

confidence: 99%

Photobreathing Zwitterionic Micelles

Niskanen

Vapaavuori

2019

ChemSystemsChem

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A significant and reversible size change (up to 80 nm, representing 100 % increase in diameter, i. e. “breathing”) of polymeric micelles of poly(styrene)‐block‐poly(3‐(4‐vinylpyridin‐1‐ium‐1‐yl)propane‐1‐sulfonate) (PS‐P4VP‐zwitter) was observed during phototriggered loading and release of spiropyran. The breathing (i. e. “inhaling/exhaling” of the small molecules by the micelles) could be controlled by switching the wavelength of the light used. Spiropyran, which was converted into the zwitterionic merocyanine by UV light, was readily diffused and incorporated into the zwitterionic micelle cores, thus causing the micelles to expand. At the same time, the merocyanine was stabilized by the polyzwitterionic core of the micelles. To the best of our knowledge, this is the first report of a supramolecular and reversibly photoloadable system that can be converted from a thermodynamically stable self‐assembled equilibrium system into a dynamic, self‐assembled system that is sustained by illumination.

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Micro-environmental fine-tuning of electronic and kinetic properties of photochromic dyes

Cited by 35 publications

References 114 publications

Tunable Morphology of Spiropyran Assemblies: From Nanospheres to Nanorods

Tunable Morphology of Spiropyran Assemblies: From Nanospheres to Nanorods

Metal complexes of the merocyanine form of nitrobenzospyran: Structure, optical spectra, stability

Photobreathing Zwitterionic Micelles

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