Lactone-fused naphthopyran UV photoswitches with fast bleaching in the dark

Sousa, Céu M.; Coelho, Paulo J.

doi:10.1016/j.jphotochem.2021.113649

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Cited by 6 publications

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“…It exhibits well separated absorption spectra for their open and closed forms, both materials absorbing in the visible spectrum (most photoswitches change from colourless to coloured). [54][55][56][57][58] It also offers a blue-shi in the absorbance upon the photochemical reaction, when the conventional effect is an absorbance displacement to the IR upon photo-excitation. [59][60][61][62][63]…”

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confidence: 99%

Truncated conjugation in fused heterocycle-based conducting polymers: when greater planarity does not enhance conjugation

et al. 2023

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Section: Discussionmentioning

confidence: 99%

Truncated conjugation in fused heterocycle-based conducting polymers: when greater planarity does not enhance conjugation

et al. 2023

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Influence of Triptycene Annulation on the Photochromism of Diphenylnaphthopyrans: Entropic Control of Thermal Reversion

Jana

Moorthy

2023

Chemistry A European J

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Regioisomeric naphthopyrans annulated with triptycene, i. e., Prox‐NP and Dist‐NP, display divergent photochromic behaviors. While steady‐state photolysis of Dist‐NP led to a very labile colored intermediate that is not observable at room temperature, Prox‐NP yielded a remarkably stable species characterized by X‐ray crystallography as the TT isomer of o‐quinonoid intermediate (Prox‐NPQ) with t1/2 ca. 0.18 years at 298 K. The kinetic analysis of thermal reversion reveals that the bleaching of Prox‐NPQ is entropically controlled; the steric effect due to the rigid triptycene scaffold renders Prox‐NP a highly constrained system such that the photogenerated colored o‐quinonoid form is more entropically relaxed. This constitutes the first instance of an entropically‐controlled thermal reversion for the celebrated class of photochromic naphthopyrans. Based on the response of Prox‐NP and its colored intermediate Prox‐NPQ to different stimuli, namely, light, heat, and acid, the molecular system can be likened to a logic gate with the ‘INHIBIT’ function.

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Experimental and theoretical study on photochromism of triphenylvinyl-naphthopyrans

Yan

et al. 2023

Dyes and Pigments

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Lactone-fused naphthopyran UV photoswitches with fast bleaching in the dark

Cited by 6 publications

References 23 publications

Truncated conjugation in fused heterocycle-based conducting polymers: when greater planarity does not enhance conjugation

Truncated conjugation in fused heterocycle-based conducting polymers: when greater planarity does not enhance conjugation

Influence of Triptycene Annulation on the Photochromism of Diphenylnaphthopyrans: Entropic Control of Thermal Reversion

Experimental and theoretical study on photochromism of triphenylvinyl-naphthopyrans

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