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Photochemistry

DASA photoswitches work in chloroform if N-methyl

Mallo N, Foley ED, Iranmanesh H, et al. · Chemical science · 2018

Open access · cc by · source: Europe PMC

First-generation donor–acceptor Stenhouse adducts with a small N-methyl substituent switch well in chloroform; kinetics split photoisomerisation from cyclisation.

Study at a glance

Design
Other — Synthesis and photoswitching kinetics/fatigue of DASA photochromes 1–14
N
Molecular photochrome SAR — no sample N
Population
Donor–acceptor Stenhouse adduct photoswitches
Outcome
Photoswitching amplitude, kinetics, and fatigue related to substituents

Structured fields used in claim comparison tables when every cited study has a complete layer.

Key findings

Most alkyl-amine DASAs share λmax ≈ 567 nm; DASA 1 drops 94% absorbance on irradiation. N-methyl is needed for good switching; ring-closing rates track substituent parameters. Fatigue can exceed 99% recovery per cycle.

Methodology

Authors prepared DASAs 1–14, assigned linear/cyclic isomers by NMR and X-ray, measured photoswitching and 100–1000 cycle fatigue, and fitted a three-species kinetic model.

Limitations

Aqueous switching is not the focus; compound 14 (aniline) behaves differently; air still causes fatigue versus argon.

How this study connects

Role on claims

Each row is a claim on a concept or method page where this paper supports, challenges, or qualifies the statement. Roles are hand-checked — not a model guess.

  • SupportsPhotochemistryconcept

    This library holds 10 empirical chemistry papers on photochemistry with isolated findings, rates or spectra rather than reviews.

    Evidence for the claim as stated.

  • SupportsPhotochemistryconcept

    First-generation donor–acceptor Stenhouse adducts with a small N-methyl substituent switch well in chloroform; kinetics split photoisomerisation from cyclisation.

    Evidence for the claim as stated.

  • SupportsPhotochemistryconcept

    Quantum yield, wavelength and quencher identity vary widely; a 'photocatalyst' can be a chain initiator rather than a closed cycle.

    Evidence for the claim as stated.

Open questions

Tensions this paper is part of

From concept pages' “where studies disagree.” Disagreement means the same question; scope means different assays, populations, or outcomes.

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