The synthesis and properties of naphthopyran– boradiazaindacene conjugates

Gabbutt, Christopher D.; Heron, B. Mark; Kilner, Colin A.; Kolla, Suresh B.

doi:10.1016/j.dyepig.2012.01.002

Cited by 11 publications

(3 citation statements)

References 42 publications

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“…Molecular design and synthesis of novel naphthopyran systems with large optical densities and fast photodynamics at ambient temperature are, therefore, essential for their industrial applications. Some studies, such as introducing COOH or CH 2 OH substituent in the five position of the naphthopyrans [4], fusing aromatic rings [5,6], annelating indeno-naphthopyrans that have an alcohol function near the oxygen pyranic atom [7], coupling with a BODIPY moiety [8], and attaching a soft segment [9], have been performed to improve these photochromic performances. However, there are few studies to utilize hydrogen boding to tune the properties of naphthopyran molecules.…”

Section: Introductionmentioning

confidence: 99%

A photochromic naphthopyran dye activated by the intramolecular hydrogen bond and its photodynamics in the ormosil matrix coating

Fang

Meng

Wang

et al. 2014

J Sol-Gel Sci Technol

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Naphthopyran dyes are one important family of photochromic compounds, and the understanding of the effects of internal and external factors on their functions is crucial to their development. In this study, the intramolecular hydrogen bond and host materials have been demonstrated to be essential to their applications. A novel N-(4-chlorophenyl)-3,3-diphenyl-3H-benzo[f]chromene-5-carboxamide (NPase) dye is designed and synthesized based on the condensation reaction of 1,1-diphenylprop-2-yn-1-ol and N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide in an acidic solution. Both the X-ray analysis of the NPase single crystal and theoretical calculation are used to investigate the molecular configuration and optical property. After the introduction of an intramolecular hydrogen bond by the substitute in the dye, an unusual coplanar structure is theoretically proposed and experimentally confirmed, which affects the tautomerization energy and bathochromic-shift in absorption characteristics greatly. Our results also confirm that the flexible segment of polymethylsiloxane (PDMS) in the host hybrid coating (PMS-PDMS) materials can accelerate the spectrokinetics of NPase which indicates a faster conversion process.

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Section: Introductionmentioning

confidence: 99%

A photochromic naphthopyran dye activated by the intramolecular hydrogen bond and its photodynamics in the ormosil matrix coating

Fang

Meng

Wang

et al. 2014

J Sol-Gel Sci Technol

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“…Some attempts were made for bonding a highly fluorescent boradiazaindacene core covalently or through hydrogen bonding to diarylethenes, spiropyrans, oxazines and recently even naphthopyrans. [13][14][15][16][17] There has also been a report on a photochromic naphthopyran bearing a fluorescent naphthalimide chromophore. 18 In this work, we report our results on the synthesis, characterization and optical properties of some new 3H-naphtho[2,1-b]pyran dyes in conjugation with stilbazolium moieties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and optical properties of naphthopyran dyes conjugated with fluorescent stilbazolium moieties

et al. 2013

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The synthesis of new 3H-naphtho[2,1-b]pyran dyes substituted at position 8 of the naphthalene ring by either a stilbazolium or an 4-ethenyl-quinolinium group and their photochemical properties are described. In non-polar media the naphthopyran-stilbazolium conjugates do not show any photochromic response while the formation of the ring opened species is promoted in strong polar media. Additional investigations of the new dyes within the pores of mesoporous MCM 41 particles showed a significant enhancement of the photochromism compared with that in solution. The generation of the ring-opened species upon irradiation with UV-light is accompanied by a decrease of the fluorescence intensity, which could be recovered by illumination with visible light

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“…[12][13][14] In addition, the colorimetric technique possesses a great advantage over other analytical methods because it has the capability to detect sulfite by the naked-eye, without the aid of any advanced instruments. [28][29][30][31][32][33][34] Thus, novel colorimetric and ratiometric fluorescent probes for sulfite with a large emission shift have become our target.…”

Section: Introductionmentioning

confidence: 99%

A Simple Levulinate-based Ratiometric Fluorescent Probe for Sulfite with a Large Emission Shift

Liu

Yang

et al. 2014

ANAL. SCI.

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A simple 4-hydroxynaphthalimide-derived colorimetric and ratiometric fluorescent probe (1) containing a receptor of levulinate moiety was designed and synthesized to monitor sulfite. Probe 1 could quantificationally detect sulfite by a ratiometric fluorescence spectroscopy method with high selectivity and sensitivity. Specially, probe 1 exhibited a 100 nm red-shifted absorption spectrum along with the color changes from colorless to yellow, and 103 nm red-shifted emission spectra upon the addition of sulfite. Thus, 1 can serve as a "naked-eye" probe for sulfite. Further, the recognition mechanism of probe 1 for sulfite was confirmed using nuclear magnetic resonance and electrospray ionization mass spectrometry. Also, the preliminary practical application demonstrated that our proposed probe provided a promising method for the determination of sulfite.

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The synthesis and properties of naphthopyran– boradiazaindacene conjugates

Cited by 11 publications

References 42 publications

A photochromic naphthopyran dye activated by the intramolecular hydrogen bond and its photodynamics in the ormosil matrix coating

A photochromic naphthopyran dye activated by the intramolecular hydrogen bond and its photodynamics in the ormosil matrix coating

Synthesis and optical properties of naphthopyran dyes conjugated with fluorescent stilbazolium moieties

A Simple Levulinate-based Ratiometric Fluorescent Probe for Sulfite with a Large Emission Shift

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