Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Frigoli, Michel; Jousselin‐Oba, Tanguy; Mamada, Masashi; Marrot, Jérôme; Zangarelli, Agnese; Pannacci, Danilo; Adachi, Chihaya; Ortica, F.

doi:10.1039/d0pp00202j

Cited by 5 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The set of sub-mechanisms worked out from Scheme 1 includes, but is not limited to, those of the primary photoprocess with a transparent photoproduct (as for photochromic diarylethenes under visible light ( Crano and Guglielmetti, 2003 ; Nakatani et al, 2016 ; Maafi and Alqarni, 2022 ; Pianowski, 2022 )), the primary photoprocess with an absorbing photoproduct (as for nifedipine, nisoldipine, and dacarbazine drugs ( Tonnesen, 2004 ; Maafi and Maafi, 2013 ; Maafi and Lee, 2015a )), the photoreversible reaction (as for stilbenoids ( Crano and Guglielmetti, 2003 ; Maafi and Al-Qarni, 2019 ), anti-cancer drugs ( Tonnesen, 2004 ; Maafi and Lee, 2015b ), and dimethylhydropropenes ( Ziani et al, 2021 )), the consecutive double photoreversible system (as for fulgides in solution or in the solid state ( Crano and Guglielmetti, 2003 ; Weerasekara et al, 2017 ; Kochman et al, 2022 ; Pianowski, 2022 ) and benzopyrans ( Frigoli et al, 2020 )), the multi-consecutive photoreaction (as for riboflavin ( Maafi and Maafi, 2016 )), and other more complex systems ( Nakatani et al, 2016 ; Scaiano, 2020 ; Malato et al, 2021 ; Pianowski, 2022 ). The mechanisms and molecular systems reviewed previously have been extensively investigated, but their photokinetic studies tended to be either performed by using the equations of thermal kinetics (e.g., first-order exponential models), using various proposed (non-analytical) equations, or employing numerical integration.…”

Section: Resultsmentioning

confidence: 99%

On photokinetics under monochromatic light

Maafi

2023

Front. Chem.

View full text Add to dashboard Cite

The properties of photokinetics under monochromatic light have not yet been fully described in the literature. In addition, for the last 120 years or so, explicit, handy model equations that can map out the kinetic behaviour of photoreactions have been lacking. These gaps in the knowledge are addressed in the present paper. Several general features of such photokinetics were investigated, including the effects of initial reactant concentration, the presence of spectator molecules, and radiation intensity. A unique equation, standing for a pseudo-integrated rate law, capable of outlining the kinetic behaviour of any photoreaction is proposed. In addition, a method that solves for quantum yields and absorption coefficients of all species of a given photoreaction is detailed. A metric (the initial velocity) has been adopted, and its reliability for the quantification of several effects was proven by theoretical derivation, Runge–Kutta numerical integration calculations and through the model equation proposed. Overall, this study shows that, under monochromatic light, photoreaction kinetics is well described by Φ-order kinetics, which is embodied by a unifying model equation. This paper is aimed at contributing to rationalising photokinetics via reliable, easy-to-use mathematical tools.

show abstract

Section: Resultsmentioning

confidence: 99%

On photokinetics under monochromatic light

Maafi

2023

Front. Chem.

View full text Add to dashboard Cite

show abstract

“…[ 30,31 ] Indeed, it is known that trans‐cis coloured isomers (TC) could upon prolonged irradiation, evolve into more stable trans–trans open isomers (TT) responsible for a persistent coloration. [ 32,33 ] These results prove that the strategy of increasing the bulkiness of the substituents attached on the indene unit is a powerful and efficient method to control the kinetics of decolouration without altering the colourability at the PSS.…”

Section: Resultsmentioning

confidence: 81%

Strategies to Improve the Photochromic Properties and Photovoltaic Performances of Naphthopyran Dyes in Dye‐Sensitized Solar Cells

Mwalukuku

Liotier

Riquelme

et al. 2023

Advanced Energy Materials

View full text Add to dashboard Cite

HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

show abstract

“…Indeed, it was demonstrated that trans-cis colored isomers could upon prolonged irradiation, evolve into the more stable transoidtrans open isomers (TT) responsible for a persistent coloration. [29] 2.3. Dye-Sensitized Solar Cells…”

Section: Dft Calculationsmentioning

confidence: 99%

Photochromic Naphthopyran Dyes Incorporating a Benzene, Thiophene, or Furan Spacer: Effect on Photochromic, Optoelectronic, and Photovoltaic Properties in Dye‐Sensitized Solar Cells

et al. 2021

View full text Add to dashboard Cite

We recently demonstrated that diaryl-naphthopyran photochromic dyes are efficient for sensitization of TiO2 mesoporous electrodes, thus allowing the fabrication of photo-chromovoltaic cells that can self-adapt their absorption of light and their generation of electricity with the light intensity. Herein we report the synthesis, the characterisation of two novel photochromic dyes based on diaryl-naphthopyran core i.e NPI-ThPh and NPI-FuPh for use in Dye Sensitized Solar Cells (DSSCs). Compared to our reference dye NPI, the molecules only vary by the nature of the spacer, a thiophene or a furan, connecting the photochromic unit and the phenyl-cyano-acrylic acid moiety used as the anchoring function. We found that swapping a phenyl for a thiophene or a furan leads to an improvement of the absorption properties of the molecules both in solution and after grafting on TiO2 electrodes, however their photochromic process becomes not fully reversible. Despite better absorption in the visible range, the new dyes show poorer photochromic and photovoltaic properties in devices compared to NPI.Thanks to UV-Vis spectroscopy, DFT calculation, electrical characterization of the cells, and impedance spectroscopy, we unravel the factors limiting their performances. Our study Received: ((will be filled in by the editorial staff))Revised: ((will be filled in by the editorial staff)) Published online: ((will be filled in by the editorial staff))The data that support the findings of this study are available from the corresponding author upon reasonable request and in the supporting information. References

show abstract

Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Abstract: Five new N-phenyl-carbazole benzopyrans bearing different substitution on one of the phenyl rings at the sp3 carbon have been synthesized. Their molecular structures were investigated by X-ray and NMR analyses...

Cited by 5 publications

References 42 publications

On photokinetics under monochromatic light

On photokinetics under monochromatic light

Strategies to Improve the Photochromic Properties and Photovoltaic Performances of Naphthopyran Dyes in Dye‐Sensitized Solar Cells

Photochromic Naphthopyran Dyes Incorporating a Benzene, Thiophene, or Furan Spacer: Effect on Photochromic, Optoelectronic, and Photovoltaic Properties in Dye‐Sensitized Solar Cells

Contact Info

Product

Resources

About