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The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety.

ABSTRACT: Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and fluorescence quantum yield. The cyclization quantum yields of these compounds increased in the order of para < ortho < meta, whereas their cycloreversion quantum yields decreased in the order of meta > para > ortho. Additionally, all of these diarylethenes functioned as effective fluorescent switches in both solution and PMMA films. Cyclic voltammograms proved that the formyl group and its position could effectively modulate the electrochemical behaviors of these diarylethene derivatives.

SUBMITTER: Wang R

PROVIDER: S-EPMC3458719 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety.

Wang Renjie R Pu Shouzhi S Liu Gang G Cui Shiqiang S

Beilstein journal of organic chemistry 20120705

Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and fluorescence quantum yield. The cyclization quantum yields of these compounds increased in the o ...[more]

PMID: 23019429

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Project description:Herein, Ni-W alloy matrixes were successfully fortified with two salen-type Schiff bases 1-((E)-(2-((E)-(2-hydroxynaphthalen-1-yl)methyleneamino)phenylimino)methyl)naphthalen-2-ol (OPD) and 1-((E)-(2-((E)-(2-hydroxynaphthalen-1-yl)methyleneamino)phenylimino)methyl)naphthalen-2-ol (PPD) as additives, of similar molecular structure but varied isomeric spacers, using a facile direct current electrodeposition technique. The resulting coatings from the additive-introduced reaction system were termed as Ni-W/OPD and Ni-W/PPD throughout the study. The deterioration process (0.5 M H2SO4), surface properties, elemental composition, functional groups, and structurs of the resultant coatings were analyzed by means of Tafel and electrochemical impedance spectroscopy, field emission scanning electron microscopy (FESEM), X-ray photoelectron spectroscopy, atomic force microscopy, energy dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, and X-ray diffraction (XRD). The bare Ni-W alloy deposition resulted in a loose microstructure with higher porosity density (12.2%), while that of additive-doped plating electrolytes resulted in a compact and dense microstructure with lesser porosity density (6.3%) and minimal porosity density (3.7%) as for Ni-W/OPD and Ni-W/PPD alloy coatings, respectively. Improved corrosion parameters presented superior corrosion characteristics of Ni-W alloy coatings from an additive (PPD)-induced bath, i.e., Ni-W/PPD. Synergetic adsorption of imine groups (N atoms), hydroxyl groups (O atoms), and aromatic electron clouds and reduction in steric hindrance produced by a larger isomeric spacer strengthened the surface adsorption of additives, yielding a fine nanocrystalline Ni-W coating with reduced porosity and well-refined grains, implying the outstanding shielding effect. Results of FESEM, AFM, and XRD analyses revealed a complete cohesion between two neighboring islands, resulting in a fine planar structure with minimal coating defects for Ni-W/PPD coatings, authenticating the corrosion parameters.

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The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety.

Publications

The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety.

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