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Peer-reviewedCC BY 4.0ACS Omega

Synthesis and Photophysical Properties of Electroactive Apocynin Derivatives as Potential Luminogens and Cellular Bioimaging Agents

  • Camila García-Aquite1
  • Luis Illicachi2
  • Joel José Montalvo Acosta3
  • Alejandro Ortiz1
  • Homero G. San-Juan-Vergara4
  • Juan D. Rodríguez5
  • Walter A. Martínez-De-La-Rosa6
  • Daniel Insuasty7
  • Alberto Insuasty1
7 affiliations
  1. 1Universidad del Valle , , ,
  2. 2Universidad Santiago de Cali , , ,
  3. 3Universidad de Cartagena , , ,
  4. 4Universidad del Norte , , Km 5 vía Puerto Colombia , ,
  5. 5Universidad Libre , , Km 5 vía Puerto Colombia , ,
  6. 6Universidad Metropolitana , , ,
  7. 7Universidad del Norte , , ,
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Abstract

This study describes the synthesis, photophysical characterization, and bioimaging properties of a series of chalcones derived from apocynin, functionalized with electroactive groups such as phenyldimethylamine (1), triphenylamine (2), tetraphenylethylene (3), and pyrene (4). These molecules featured donor−π–acceptor–donor (D−π–A–D) type architectures designed to promote intramolecular charge transfer (ICT) processes and notable emissive properties. Compounds 1 and 2 exhibited a marked aggregation-caused quenching (ACQ) behavior in THF/water mixtures while compounds 3 and 4 showed a marked enhancement of emission upon aggregation (AIE), associated with the restriction of intramolecular motions in the aggregated state. DFT/TD-DFT calculations and electrochemical studies revealed good electronic communications between the electroactive units. Cellular bioimaging studies performed on compounds 1–4 showed that only compounds 1, 2, and 4 are good fluorescent agents exhibiting notable cellular permeability in HEp-2 carcinoma cells. Overall, these findings demonstrate that apocynin α,β-unsaturated systems constitute versatile luminescent platforms with tunable photophysical properties, suitable for applications in cellular bioimaging and the development of remarkable fluorescent materials.

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Cite

BibTeXRIS
BibTeX
@article{garciaaquite2026synthesis,
  title = {{Synthesis and Photophysical Properties of Electroactive Apocynin Derivatives as Potential Luminogens and Cellular Bioimaging Agents}},
  author = {Camila García-Aquite and Luis Illicachi and Joel José Montalvo Acosta and Alejandro Ortiz and Homero G. San-Juan-Vergara and Juan D. Rodríguez and Walter A. Martínez-De-La-Rosa and Daniel Insuasty and Alberto Insuasty},
  journal = {ACS Omega},
  year = {2026},
  month = oct,
  doi = {10.1021/acsomega.6c09229},
  url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c09229/5458095/Synthesis-and-Photophysical-Properties-of},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Synthesis and Photophysical Properties of Electroactive Apocynin Derivatives as Potential Luminogens and Cellular Bioimaging Agents
AU  - Camila García-Aquite
AU  - Luis Illicachi
AU  - Joel José Montalvo Acosta
AU  - Alejandro Ortiz
AU  - Homero G. San-Juan-Vergara
AU  - Juan D. Rodríguez
AU  - Walter A. Martínez-De-La-Rosa
AU  - Daniel Insuasty
AU  - Alberto Insuasty
PY  - 2026
DA  - 2026/10/26
JO  - ACS Omega
DO  - 10.1021/acsomega.6c09229
UR  - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c09229/5458095/Synthesis-and-Photophysical-Properties-of
AB  - This study describes the synthesis, photophysical characterization, and bioimaging properties of a series of chalcones derived from apocynin, functionalized with electroactive groups such as phenyldimethylamine (1), triphenylamine (2), tetraphenylethylene (3), and pyrene (4). These molecules featured donor−π–acceptor–donor (D−π–A–D) type architectures designed to promote intramolecular charge transfer (ICT) processes and notable emissive properties. Compounds 1 and 2 exhibited a marked aggregation-caused quenching (ACQ) behavior in THF/water mixtures while compounds 3 and 4 showed a marked enhancement of emission upon aggregation (AIE), associated with the restriction of intramolecular motions in the aggregated state. DFT/TD-DFT calculations and electrochemical studies revealed good electronic communications between the electroactive units. Cellular bioimaging studies performed on compounds 1–4 showed that only compounds 1, 2, and 4 are good fluorescent agents exhibiting notable cellular permeability in HEp-2 carcinoma cells. Overall, these findings demonstrate that apocynin α,β-unsaturated systems constitute versatile luminescent platforms with tunable photophysical properties, suitable for applications in cellular bioimaging and the development of remarkable fluorescent materials.
SN  - 2470-1343
ER  -