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Peer-reviewedCC BYLuminescence : the journal of biological and chemical luminescence

Tuning the Molecular Rotor Dynamics of Pyrrolo[3,4-b]Pyridin-5-Ones: Steric and Electronic Control of Environmental Sensing.

  • Ivette Morales-Salazar1
  • Carlos E Garduño Albino1
  • Alejandro Valderrama-Celestino2
  • Federico González-García3
  • Alberto Rojas1
  • Annia Galano1
  • Yoarhy A Amador-Sánchez1
  • Cesar A Guarin4
  • Eduardo González-Zamora1
  • Alejandro Islas-Jácome1
4 affiliations
  1. 1Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Ciudad de México, Mexico.
  2. 2Department of Chemistry and Biochemistry, Baylor University, Waco, Texas, USA.
  3. 3Departamento de Ingeniería de Procesos e Hidráulica, Universidad Autónoma Metropolitana-Iztapalapa, Ciudad de México, Mexico.
  4. 4Departamento de Física, Universidad Autónoma Metropolitana-Iztapalapa, Ciudad de México, Mexico.
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Abstract

A series of seven pyrrolo[3,4-b]pyridin-5-ones were synthesized via a one-pot process involving an Ugi-Zhu reaction followed by a cascade sequence (N-acylation/aza Diels-Alder cycloaddition/decarboxylation/dehydration) incorporating different substituents no aromatic and aromatic such as furan, tetrahydrofuran, and pyridine. The pyrrolo[3,4-b]pyridin-5-ones were optically characterized through their photoluminescence spectra, quantum yields, and fluorescence lifetimes. By combining spectroscopic measurements with DFT/TDDFT calculations, photophysical behavior was elucidated, specifically addressing solvent effects on transition magnitudes and the electronic nature of absorption and emission states. Structure-property relationship analyses revealed that steric and electronic substituent effects govern the interplay between charge-transfer (CT) and locally excited (LE) states. Finally, the most promising candidates were successfully evaluated as fluorogenic microviscosity and polarity sensors, demonstrating their potential for advanced sensing applications.

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Cite

BibTeXRIS
BibTeX
@article{moralessalazar2026tuning,
  title = {{Tuning the Molecular Rotor Dynamics of Pyrrolo[3,4-b]Pyridin-5-Ones: Steric and Electronic Control of Environmental Sensing.}},
  author = {Ivette Morales-Salazar and Carlos E Garduño Albino and Alejandro Valderrama-Celestino and Federico González-García and Alberto Rojas and Annia Galano and Yoarhy A Amador-Sánchez and Cesar A Guarin and Eduardo González-Zamora and Alejandro Islas-Jácome},
  journal = {Luminescence : the journal of biological and chemical luminescence},
  year = {2026},
  month = oct,
  doi = {10.1002/bio.70655},
  url = {https://europepmc.org/article/MED/42905480},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Tuning the Molecular Rotor Dynamics of Pyrrolo[3,4-b]Pyridin-5-Ones: Steric and Electronic Control of Environmental Sensing.
AU  - Ivette Morales-Salazar
AU  - Carlos E Garduño Albino
AU  - Alejandro Valderrama-Celestino
AU  - Federico González-García
AU  - Alberto Rojas
AU  - Annia Galano
AU  - Yoarhy A Amador-Sánchez
AU  - Cesar A Guarin
AU  - Eduardo González-Zamora
AU  - Alejandro Islas-Jácome
PY  - 2026
DA  - 2026/10/01
JO  - Luminescence : the journal of biological and chemical luminescence
DO  - 10.1002/bio.70655
UR  - https://europepmc.org/article/MED/42905480
AB  - A series of seven pyrrolo[3,4-b]pyridin-5-ones were synthesized via a one-pot process involving an Ugi-Zhu reaction followed by a cascade sequence (N-acylation/aza Diels-Alder cycloaddition/decarboxylation/dehydration) incorporating different substituents no aromatic and aromatic such as furan, tetrahydrofuran, and pyridine. The pyrrolo[3,4-b]pyridin-5-ones were optically characterized through their photoluminescence spectra, quantum yields, and fluorescence lifetimes. By combining spectroscopic measurements with DFT/TDDFT calculations, photophysical behavior was elucidated, specifically addressing solvent effects on transition magnitudes and the electronic nature of absorption and emission states. Structure-property relationship analyses revealed that steric and electronic substituent effects govern the interplay between charge-transfer (CT) and locally excited (LE) states. Finally, the most promising candidates were successfully evaluated as fluorogenic microviscosity and polarity sensors, demonstrating their potential for advanced sensing applications.
SN  - 1522-7235
SN  - 1522-7243
ER  -