Electrochemical reduction and oxidation of some photochromic compounds

Saraç, A. Sezai̊; Ustamehmetoğlu, Belkıs; Leiminer, A.; Stephan, Barbara; Mannschreck, Albrecht

doi:10.1016/s0013-4686(97)00030-3

Cited by 8 publications

(8 citation statements)

References 15 publications

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“…A similar trend was also observed in the spectroelectrochemical study of these compounds, i.e. except for SP 2 , the other spirochromenes show electrochromism (at 2.0 V applied potential), supporting the idea of resistance in the ring opening process in the case of SP 2 [4]. Figure 3 shows the decoloration kinetics of SP 1 , SP 2 , SP 3 and SP 4 at 50°C.…”

Section: Ring Opening Process Of Other Spirocompounds By Photoproducesupporting

confidence: 80%

“…Preliminary investigations suggested that both oxidative and reductive processes may be relevant in the degradation of these compounds [3]. In order to gain further insight into the properties of both the closed and open forms of them, we recently reported the electrochemical behavior of some photochromic compounds [4] of which four were investigated in this study.…”

Section: (Coloured)mentioning

confidence: 99%

“…In the photosensitive system, the three major components are PVCz, CCl 4 and SP at average ratios of 5, 1 and 0.1 respectively in dichloromethane.…”

Section: Preparationmentioning

confidence: 99%

“…In this part, the system contains PVCz CCl 4 (instead of CBr 4 ) [6] and spirochromenes (SP 1 , SP 2 , SP 3 , SP 4 ) at an average molar ratio of 5, 1 and 0.1 respectively [5]. The addition of reactants was performed in two steps.…”

Section: Ring Opening Process Of Sp 3 By Photoproduced Hclmentioning

confidence: 99%

See 3 more Smart Citations

Ring opening process of some spirochromenes by photoproduced HCl in poly(N-vinyl carbazole)

Sarac

Sezer

Ustamehmetoğlu

et al. 1997

Polym. Adv. Technol.

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The coloration reaction of some spirochromenes (SP) has been investigated in the case of a free radical photosensitive system composed of a poly(N‐vinylcarbazole) matrix (PVCz) in dichloromethane containing carbon tetrachloride as an activator at average ratios of 5:1:0.1 for PVCz, CCl4 and SP, respectively. In this system, photoproduced HCl leads to the formation of the colored forms of SP. Acidification and irradiation of the variety of spirochromene solutions in the presence and absence of PVCz were also investigated and compared with the effect of photoproduced HCl on the reversibility of the ring opening process. The opened forms of the compounds were characterized by UV–visible spectra, pH and conductivity measurements. The effect of solvent and the substituent of SP were investigated. Decoloration reactions of the opened forms of SP at 50°C were followed using UV–visible spectroscopy, pH and conductivity measurements. © 1997 John Wiley & Sons, Ltd.

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Section: Ring Opening Process Of Other Spirocompounds By Photoproducesupporting

confidence: 80%

Section: (Coloured)mentioning

confidence: 99%

“…In the photosensitive system, the three major components are PVCz, CCl 4 and SP at average ratios of 5, 1 and 0.1 respectively in dichloromethane.…”

Section: Preparationmentioning

confidence: 99%

Section: Ring Opening Process Of Sp 3 By Photoproduced Hclmentioning

confidence: 99%

See 2 more Smart Citations

Ring opening process of some spirochromenes by photoproduced HCl in poly(N-vinyl carbazole)

Sarac

Sezer

Ustamehmetoğlu

et al. 1997

Polym. Adv. Technol.

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“…optical devices, smart windows, electronic data storages, and light-sensitive sunglasses. In order to gain further insight into the properties of both the closed and open forms of these compounds we have studied both electrochemical reduction and oxidation of 11 different spirocompounds by electrochemically inducing of radical ions [1]. The electronic structures of the same compounds have also been confirmed with semiempirical quantum mechanical calculations [2].…”

mentioning

confidence: 99%

Matrix effect on the electrochromism of spirochromics

1999

Polym. Adv. Technol.

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The reduction of six spirocompounds in the absence and presence of polymethylmethacrylate (PMMA) matrix was investigated by in situ spectrochemical measurements. The effect of polymer concentration and chemical structure of spirocompounds on the electrochromism in solution was investigated and an advantage of the presence of the PMMA matrix for two spirooxazine compounds in the bleaching process was reported. The vertical ionization potentials obtained with semiempirical quantum mechanical calculations and those obtained from λmax of the sample solutions in PMMA proved to be consistent with oxidation potentials obtained from cyclic voltammetry experiments. This correlation can be explained by the stability of compounds in the PMMA matrix. Copyright © 1999 John Wiley & Sons, Ltd.

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A quantum mechanical approach to electrochemical behavior of spirochromics

Yurtsever

Ustamehmetoğlu

Sarac

et al. 1999

Int. J. Quant. Chem.

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ABSTRACT:Fully optimized semiempirical quantum-chemical calculations of photochromic spiropyrans are presented. The vertical ionization potentials are calculated and their variation with substitutions are correlated to experimental oxidation potentials. The effects of the substitutions are studied and the partial charges on indoline and pyran components generated by HOMO are found to be responsible for the variations. The deactivating groups on the indoline ring system and deactivating groups on the pyran system increase the ionization potential and, consecutively, the oxidation potential.

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Electrochemical reduction and oxidation of some photochromic compounds

Cited by 8 publications

References 15 publications

Ring opening process of some spirochromenes by photoproduced HCl in poly(N-vinyl carbazole)

Ring opening process of some spirochromenes by photoproduced HCl in poly(N-vinyl carbazole)

Matrix effect on the electrochromism of spirochromics

A quantum mechanical approach to electrochemical behavior of spirochromics

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