Novel synthesis and characterisation of 3,3-dimethyl-5′-(2-benzothiazolyl)-spironaphth(indoline-2,3′-[3H]naphth[2,1-b] [1,4]oxazine) derivatives

Alhashimy, Nameer; Byrne, Robert; Minkovska, Stela; Diamond, Dermot

doi:10.1016/j.tetlet.2009.03.080

Cited by 18 publications

(5 citation statements)

References 47 publications

(20 reference statements)

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“…reported that the cyclic isomers of benzothiazolyl‐spironaphthopyran derivatives possess a longest wavelength absorption band at 381–404 nm. Upon irradiation of these cyclic compounds with UV light in acetone, the photomerocyanine was formed as expected17 with a new absorption band centered at 640 nm, and these results corroborate our study.…”

Section: Resultssupporting

confidence: 90%

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water

Mahapatra

Maiti

Manna

et al. 2014

Chemistry An Asian Journal

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A new benzimidazole-spiropyran conjugate chemosensor molecule (BISP) has been synthesized and characterized by (1)H NMR spectroscopy, mass spectrometry (ESI-MS), and elemental analysis. The two isomeric forms (BISP↔BIMC) were shown to be highly selective and sensitive to CN(-) among the ten anions studied in aqueous HEPES buffer, as shown by fluorescence and absorption spectroscopy and even by visual color changes, with a detection limit of 1.7 μM for BIMC. The reaction of CN(-) with BIMC was monitored by (1)H NMR spectroscopy, high-resolution mass spectrometry (HRMS), UV/Vis measurements, and fluorescence spectroscopy in HEPES buffer of pH 7.4. TDDFT calculations were performed in order to correlate the electronic properties of the chemosensor with its cyanide complex. Further, titration against thiophilic metal ions like Au(3+), Cu(2+), Ag(+), and Hg(2+) with [BIMC-CN] in situ showed that it acts as a secondary recognition ensemble toward Au(3+) and Cu(2+) by switch-on fluorescence. In addition, a reversible logic-gate property of BIMC has been demonstrated through a feedback loop in the presence of CN(-) and Au(3+) ions, respectively. Furthermore, the use of BIMC to detect CN(-) in live cells by fluorescence imaging has also been demonstrated. Notably, test strips based on BIMC were fabricated, which could serve as convenient and efficient CN(-) test kits.

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Section: Resultssupporting

confidence: 90%

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water

Mahapatra

Maiti

Manna

et al. 2014

Chemistry An Asian Journal

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“…In some instances, the ring-opening reaction may also be induced in the dark through the addition of particular metal cations that are able to coordinate to the phenolate oxygen atom and/or other additional coordinating atoms and substituents that have been introduced into the structure of the spirooxazine and spiropyran derivatives [17][18][19][20][21][22][23][24][25][26]. Regardless of whether the ring-opening reaction is induced by cations or irradiation, the coordination of metal ions to the substrate usually results in a negative photochromism, i.e., a blue shift of the absorption maximum of the merocyanine form [5,19,[27][28][29], and increased stability of the latter towards the thermal back reaction [21,28,[30][31][32][33][34]. In this context, the complexation of metal cations has also been exploited to utilize this compound class for the development of photochromic chemosensors that allow the colorimetric or fluorimetric detection of particular analytes [5,29,[35][36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Pithan¹,

Ihmels²

2020

Beilstein J. Org. Chem.

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Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectrometric studies that the addition of particular metal ions (Cu2+, Fe3+, and to a certain extent Hg2+) initially induced a ring-opening reaction that was irreversibly followed by a fast ring closure–deprotonation–oxidation sequence to give styryl-substituted naphthoxazole derivatives as the products quantitatively. For the quinolizinium-substituted spirooxazine derivative, the formation of the respective oxidation product caused the development of a broad absorption band between 425 nm and 500 nm and a new emission band at λfl = 628 nm, so that it may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3+.

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“…Several reports of spiropyran derivatives with a second chelating group or a crown ether attached to spiropyran to aid in metal ion binding have been detailed in the literature. [22][23][24][25][26][27][28][29] However, in these reports an in-depth analysis of the interaction between ligand and metal ion for a variety of metal ions has not been studied. A better understanding of the complexation would open the possibility of designing spiropyran-based receptors for selective binding of metal ions.…”

Section: Introductionmentioning

confidence: 99%

Tuning chelating groups and comonomers in spiropyran-containing copolymer thin films for color-specific metal ion binding

et al. 2014

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Photochromic molecules can be used to selectively bind divalent metal ions. In order to study the influence of increased chelation in spiropyran-containing copolymers, we synthesized two derivatives: spiropyran methacrylate (SPMA) and spiropyran methacrylate with a methoxy substituent in the 8 0 position of the benzopyran ring (MEO). Additionally, the comonomer with which spiropyran was polymerized is also varied between methyl methacrylate (MMA) and 2,2,2-trifluoroethyl methacrylate (TFEMA) to tune the colorimetric response. Fourier transform-infrared (FT-IR) spectroscopy was used to characterize the photoinduced conversion of spiropyran to merocyanine, as well as the merocyanine-metal ion (MC-M 2+ ) interaction. By means of UV-Vis absorption spectroscopy, we demonstrate that each metal ion gives rise to a unique colorimetric response for the various spiropyran-containing copolymers studied.

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Novel synthesis and characterisation of 3,3-dimethyl-5′-(2-benzothiazolyl)-spironaphth(indoline-2,3′-[3H]naphth[2,1-b] [1,4]oxazine) derivatives

Cited by 18 publications

References 47 publications

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Tuning chelating groups and comonomers in spiropyran-containing copolymer thin films for color-specific metal ion binding

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Novel synthesis and characterisation of 3,3-dimethyl-5′-(2-benzothiazolyl)-spironaphth(indoline-2,3′-[3H]naphth[2,1-b] [1,4]oxazine) derivatives

Cited by 18 publications

References 47 publications

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN− in Water

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN− in Water

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Tuning chelating groups and comonomers in spiropyran-containing copolymer thin films for color-specific metal ion binding

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Product

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Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water

Unique Fluorogenic Ratiometric Fluorescent Chemodosimeter for Rapid Sensing of CN⁻ in Water