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Peer-reviewedCC BYCommunications Chemistry

Exploring the photodynamical landscape of biomimetic lumichrome–ephedrine-class amine complexes across femtosecond to millisecond regimes

  • Subhrakant Jena1
  • Mario de la Hoz Tomás1
  • Juan Ángel Organero1
  • Miquel Moreno Ferrer2
  • Abderrazzak Douhal1
  1. 1Departamento de Química Física, Facultad de Ciencias Ambientales y Bioquímica, y INAMOL, Universidad de Castilla-La Mancha, Avenida Carlos III, S/N
  2. 2Departament de Química, Universitat Autònoma de Barcelona
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Abstract

Flavin–amine interactions are central to neurotransmitter metabolism, yet how H-bonding and amine structure govern excited-state pathways remains unclear. Using lumichrome (LC) as a biomimetic model, we examine interactions and photobehaviour with sympathomimetic amines, norephedrine (Neph), ephedrine (Eph), and pseudoephedrine (Peph). In water, LC with amines readily forms anions. In dichloromethane, H-bonding drives ultrafast single-proton transfer (SPT) in the LC–Neph complex (~800 fs), followed by population redistribution (~14 ps) and a long-lived anion (τ ~5.4 ns), while LC–Eph and LC–Peph complexes show shorter lifetimes (~4.3–4.8 ns). Control experiments with phenethylamine confirm that the amine group drives SPT-mediated anion formation. Computational calculations support excitation-induced charge redistribution and SPT-mediated zwitterionic stabilisation. Nanosecond-millisecond transient absorption shows minor triplet quenching by Neph (τ ~0.74 → 0.66 μs), but Eph and Peph enhance quenching (τ ~0.45-0.55 μs) and photoproduct formation. This study unravels LC–sympathomimetic amine interactions, offering an avenue to interrogate excited-state pathways in flavin photochemistry.

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Cite

BibTeXRIS
BibTeX
@article{jena2026exploring,
  title = {{Exploring the photodynamical landscape of biomimetic lumichrome–ephedrine-class amine complexes across femtosecond to millisecond regimes}},
  author = {Subhrakant Jena and Mario de la Hoz Tomás and Juan Ángel Organero and Miquel Moreno Ferrer and Abderrazzak Douhal},
  journal = {Communications Chemistry},
  year = {2026},
  month = jul,
  doi = {10.1038/s42004-026-02110-7},
  url = {https://doi.org/10.1038/s42004-026-02110-7},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Exploring the photodynamical landscape of biomimetic lumichrome–ephedrine-class amine complexes across femtosecond to millisecond regimes
AU  - Subhrakant Jena
AU  - Mario de la Hoz Tomás
AU  - Juan Ángel Organero
AU  - Miquel Moreno Ferrer
AU  - Abderrazzak Douhal
PY  - 2026
DA  - 2026/07/01
JO  - Communications Chemistry
DO  - 10.1038/s42004-026-02110-7
UR  - https://doi.org/10.1038/s42004-026-02110-7
AB  - Flavin–amine interactions are central to neurotransmitter metabolism, yet how H-bonding and amine structure govern excited-state pathways remains unclear. Using lumichrome (LC) as a biomimetic model, we examine interactions and photobehaviour with sympathomimetic amines, norephedrine (Neph), ephedrine (Eph), and pseudoephedrine (Peph). In water, LC with amines readily forms anions. In dichloromethane, H-bonding drives ultrafast single-proton transfer (SPT) in the LC–Neph complex (~800 fs), followed by population redistribution (~14 ps) and a long-lived anion (τ ~5.4 ns), while LC–Eph and LC–Peph complexes show shorter lifetimes (~4.3–4.8 ns). Control experiments with phenethylamine confirm that the amine group drives SPT-mediated anion formation. Computational calculations support excitation-induced charge redistribution and SPT-mediated zwitterionic stabilisation. Nanosecond-millisecond transient absorption shows minor triplet quenching by Neph (τ ~0.74 → 0.66 μs), but Eph and Peph enhance quenching (τ ~0.45-0.55 μs) and photoproduct formation. This study unravels LC–sympathomimetic amine interactions, offering an avenue to interrogate excited-state pathways in flavin photochemistry.
SN  - 2399-3669
ER  -