The synthesis and spectroscopic properties of novel, photochromic indolinobenzospiropyran-based homopolymers prepared via ring-opening metathesis polymerization

Keum, Sam‐Rok; Ahn, Su-Mi; Roh, Se-Jung; Ma, So-Young

doi:10.1016/j.dyepig.2009.12.002

Cited by 24 publications

(21 citation statements)

References 41 publications

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“…The synthesis concept for SP-OH (4) and the active ester mediated coupling of the norbornene polymerizable unit (5) to SP-OH (4) are based on previously reported studies. [33][34][35] The NMR analysis shows a pure SP-Nb monomer (6) with a total yield of around 20% after four reaction steps, which is close to the literature yield of 25%. 33 This synthetic approach is successfully transferred to SPO-Nb (7) with a comparable total yield.…”

Section: Synthesis Of Spiropyran and Spirooxazine Monomerssupporting

confidence: 83%

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

et al. 2016

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Section: Synthesis Of Spiropyran and Spirooxazine Monomerssupporting

confidence: 83%

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

et al. 2016

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“…The monomer (SP-norbornene) was prepared from the reaction of exo-5-norbornyl carboxylic acid with SP1 in the presence of N,N′-Dicyclohexylcarbodiimide (DCC) and 4-(Dimethylamino) pyridine (DMAP) as described elsewhere [34,35]. For the SP-norbornene and poly (SP-norbornene) synthesis, dry tetrahydrofuran and dry dichloromethane solvents were purchased from Sigma-Aldrich and used as received.…”

Section: Methodsmentioning

confidence: 99%

Microcantilever arrays functionalised with spiropyran photoactive moieties as systems to measure photo-induced surface stress changes

Grogan¹,

Florea

Koprivica

et al. 2016

Sensors and Actuators B: Chemical

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Herein we investigate the feasibility of detecting photo-induced surface stress changes using the deflection response of cantilevers. For this purpose, silicon microcantilevers have been functionalised with spiropyran photochromic molecules, using both a monolayer and a polymeric brushes approach. Upon ultraviolet light irradiation, the spiropyran unit is converted to the merocyanine form due to the photo-induced cleavage of the C spiro -O bond. The two forms of the molecule have dramatically different charge, polarity and molecular conformations. This makes spiropyrans an ideal system to study the correlation between photo-induced molecular changes and corresponding changes in surface stress. Our investigations include monitoring the changes in static cantilever deflection, and consequently, surface stress of the spiropyran functionalised cantilevers on exposure to ultraviolet light. Cantilever deflection data reveals that ultraviolet induced conformational changes in the spiropyran moiety cause a change in compressive surface 2 stress and this varies with the type of functionalisation method implemented. The change in surface stress response from the spiropyran polymer brushes functionalised cantilevers gives an average surface stress change of 98 Nm -1 (n = 8) while the spiropyran monolayer coated cantilevers have an average surface stress change of about 446 Nm -1 (n = 24) upon irradiation with UV light.

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“…1 H NMR (CDCl 3 , 600 MHz), δ (ppm) = 11.3 (s, 1H), 9.96 (s, 1H), 7.89 (s, 1H), 7.78 (d, 1H), 7.13 (d, 1H) (Figure S1). Then, 1‐(2‐carboxyethyl)‐2,3,3‐trimetyl‐3H‐indolium bromide was synthesized following a modified published procedure . An orange solid was obtained with a 59.0% yield.…”

Section: Methodsmentioning

confidence: 99%

“…In the last step, L was prepared from 5‐cyanosalicylaldehyde and 1‐(2‐carboxyethyl)‐2,3,3‐trimetyl‐3H‐indolium bromide as previously reported, with some modifications . Briefly, a mixed solution of 1‐(2‐carboxyethyl)‐2,3,3‐trimetyl‐3H‐indolium bromide (100 mg, 0.320 mmol) and 5‐cyanosalicylaldehyde (40.0 mg, 0.270 mmol), and triethylamine (0.600 mL) in ethanol (10.0 mL) was refluxed in the dark for 19 h. Evaporation of the solvent left a purple powdery solid.…”

Section: Methodsmentioning

confidence: 99%

Selective sensing Ca²⁺ with a spiropyran‐based fluorometric probe

et al. 2019

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Spiropyran (SP) and its derivatives operate between their ring opening and closing forms as a versatile molecular platform for the fluorescence detection of cations and anions, using a colour change for signalling. A functionalized SP fluorescence probe, L, was prepared and characterized. Probe L can detect Ca 2+ with a fluorescence 'turn-on' response in ethanol solution. It selectively binds Ca 2+ to form a 1:1 ligand/metal complex, which produced a new emission band centred at 604 nm. The sensing result was clearly observed by the solution colour change from colourless to pink under visible light, and from blue to red under ultraviolet light. The detection limit was calculated to be 4.53 × 10 −8 M for Ca 2+ . The probe provides another possibility that SP-based derivatives could be used for the development and detection of metal ions in environmental and physiological systems.

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The synthesis and spectroscopic properties of novel, photochromic indolinobenzospiropyran-based homopolymers prepared via ring-opening metathesis polymerization

Cited by 24 publications

References 41 publications

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

Microcantilever arrays functionalised with spiropyran photoactive moieties as systems to measure photo-induced surface stress changes

Selective sensing Ca²⁺ with a spiropyran‐based fluorometric probe

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The synthesis and spectroscopic properties of novel, photochromic indolinobenzospiropyran-based homopolymers prepared via ring-opening metathesis polymerization

Cited by 24 publications

References 41 publications

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

Photochromic spiropyran- and spirooxazine-homopolymers in mesoporous thin films by surface initiated ROMP

Microcantilever arrays functionalised with spiropyran photoactive moieties as systems to measure photo-induced surface stress changes

Selective sensing Ca2+ with a spiropyran‐based fluorometric probe

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Selective sensing Ca²⁺ with a spiropyran‐based fluorometric probe