Overview

The main objective of GICOBIORG is to continue to stand out in the area of Organic Chemistry through its research. As a result, the group has published more than fifty research articles, several review articles, and some book chapters. Since 2016, the group's work has focused mainly on synthesizing nitrogenous heterocyclic compounds with biological (1) and photophysical (2) potential using simple and ecological approaches, for example, by reactions induced by microwave (MW) or ultrasound (US) radiation. The image shows the MW and US equipment used by our laboratory.

As a result of its research, GICOBIORG has obtained many new functionalized molecules, leading to appropriate interdisciplinarity reflected in his most recent work (since 2015). GICOBIORG's research work has also been disclosed in various specialized scientific events (in America, Europe, etc.), four doctoral theses have been held (3 with a scholarship from MINCIENCIAS - Ministerio de Ciencia, Tecnología e Innovación), and more than 12 master's degrees, more than 20 undergraduate projects and four postdoctoral assistant contracts (two with resources from MINCIENCIAS). The group also links collaboration with several national and international research centers (in America and Europe).

Research Topics

As already mentioned, the research carried out at GICOBIORG focuses on ecological synthesis strategies, with a particular interest in obtaining N-heterocyclic compounds with biological (1) and photophysical (2) potential, as well as the correlation of these properties with the solid state. Current projects focus on:

1. Compounds of biological interest.
   - Azole antifungal compound derivatives containing the privileged 2-haloaryl-2-hydroxyethyl moiety on the pyrrole-type nitrogen atom on imidazole, triazole, or benzimidazole rings.
   - Synthesis of compounds with potential antitumor or antimicrobial activity with a simple or fused structure (pyrazoles, imidazoles, benzimidazoles, pyrazolopyrimidines, etc.), which, in general, are substituted with halogen atoms (F, Cl) and alkoxyl groups.

2. Compounds of photophysical interest. Synthesis and functionalization of fluorescent heterocyclic compounds of π-extended conjugation, which have pyrazole, coumarin, pyrazolopyrimidine, bis-pyrazolopyridine, pyrroloquinoline, and benzimidazole rings. These molecules possess important fluorochromes (i.e., triphenylamine, coumarin, alkoxyaryl, pyrenyl, or fluorenyl rings) that are appropriately substituted for molecular probes designed for the detection of ions (anions and cations) of biological and environmental interest. These compounds are investigated for their solvatofluorochromism and nonlinear optical properties towards the design of chemosensors and/or materials of optoelectronic importance.

Relevant articles in each year since 2015

1. Orrego-Hernández, J.; Cobo, J.; Portilla, J. Chemoselective Synthesis of 5-Alkylamino-1H-Pyrazole-4-Carbaldehydes by Cesium- and Copper-Mediated Amination. Eur. J. Org. Chem. 2015, 2015 (23). https://doi.org/10.1002/ejoc.201500505.
2. Orrego-Hernández, J.; Nuñez-Dallos, N.; Portilla, J. Recognition of Mg²⁺ by a New Fluorescent “Turn-on” Chemosensor Based on Pyridyl-Hydrazono-Coumarin. Talanta 2016, 152, 432–437. https://doi.org/10.1016/j.talanta.2016.02.020.
3. Charris-Molina, A.; Castillo, J.-C.; Macías, M.; Portilla, J. One-Step Synthesis of Fully Functionalized Pyrazolo[3,4-b]Pyridines via Isobenzofuranone Ring Opening. J. Org. Chem. 2017, 82 (23). https://doi.org/10.1021/acs.joc.7b02471.
4. Castillo, J. C.; Tigreros, A.; Portilla, J. 3-Formylpyrazolo[1,5-a]Pyrimidines as Key Intermediates for the Preparation of Functional Fluorophores. J. Org. Chem. 2018, 83 (18), 10887–10897. https://doi.org/10.1021/acs.joc.8b01571.
5. Tigreros, A.; Rosero, H.-A.; Castillo, J.-C.; Portilla, J. Integrated Pyrazolo[1,5-a]Pyrimidine–Hemicyanine System as a Colorimetric and Fluorometric Chemosensor for Cyanide Recognition in Water. Talanta 2019, 196, 395–401. https://doi.org/https://doi.org/10.1016/j.talanta.2018.12.100.
6. Tigreros, A.; Aranzazu, S.-L.; Bravo, N.-F.; Zapata-Rivera, J.; Portilla, J. Pyrazolo[1,5-a]Pyrimidines Based Fluorophores: A Comprehensive Theoretical-Experimental Study. RSC Adv. 2020, 10, 39542–39552. https://doi.org/https://doi.org/10.1039/D0RA07716J.
7. Tigreros, A.; Zapata-Rivera, J.; Portilla, J. Pyrazolo[1,5-a]Pyrimidinium Salts for Cyanide Sensing: A Performance and Sustainability Study of the Probes. ACS Sustain. Chem. & Eng. 2021, 9 (36), 12058–12069. https://doi.org/10.1021/acssuschemeng.1c01689.
8. Aranzazu, S. L.; Tigreros, A.; Arias-Gómez, A.; Zapata-Rivera, J.; Portilla, J. BF₃-Mediated Acetylation of Pyrazolo[1,5-a]Pyrimidines and Other π-Excedent (N-Hetero)Arenes. J. Org. Chem. 2022, 87 (15), 9839–9850. https://doi.org/10.1021/acs.joc.2c00881.